My D*ck is Exhausted with Boom Boom "Jeff" Hiller

Summary

Podcast Summary: "My D*ck is Exhausted with Boom Boom 'Jeff' Hiller"

Episode Information:

• Title: My D*ck is Exhausted with Boom Boom "Jeff" Hiller
• Release Date: July 3, 2025
• Host/Author: iHeartPodcasts, hosted by Chelsea Handler and co-host Catherine Law
• Guest: Jeff Hiller (known as Boom Boom Hiller)

---

1. Introduction to Jeff Hiller

[02:18] Katherine: "We have a really fun guest today... his name is Jeff Hiller."

[03:38] Katherine: Introduces Jeff Hiller, affectionately dubbed "Boom Boom," highlighting his popularity from the HBO show Somebody Somewhere.

---

2. Upbringing and Early Struggles

Jeff shares his experiences growing up in Texas as a gay boy, dealing with bullying, and how these challenges shaped his resilience and humor.

[04:34] Jeff Hiller: "I think that's why I'm funny now. I think that was like a self coping mechanism, you know, to try and make you laugh so you won't hit me."

[05:04] Katherine: "Your childhood in school and the torturing or the teasing and the bullying just sounded terrible."

Jeff reflects on how bullying, while harsh, inadvertently built his character and comedic talent.

[07:17] Jeff Hiller: "I think I could have gotten sufficient character with just, you know, 80% less torture."

---

3. Career and Book: Actress of a Certain Age

Jeff discusses his book, Actress of a Certain Age: My 20-Year Trail to Overnight Success, sharing humorous and humiliating stories from his auditions and early career.

[04:11] Katherine: "Boom Boom, otherwise known as Jeff Hiller, has a new book called Actress of a certain age. My 20-year trail to Overnight Success."

[10:33] Katherine: "There is two scenes that I'm thinking of right off the top of my head... waxing the butthole."

[10:45] Jeff Hiller: Recounts a particularly embarrassing audition scene involving laser hair removal on an actor's butthole, humorously titled "Leather Cheerio."

---

4. Navigating Success and Timelines

The hosts and Jeff delve into societal expectations around success timelines, emphasizing flexibility and personal growth over rigid benchmarks.

[13:45] Katherine: "People have these timelines... I always thought, as long as by 32, if I've got my... that's so silly and so stupid."

[14:12] Jeff Hiller: "Nobody wants to hire you when you're like, please, please hire me. I've only got this one season left."

They discuss how success often arrives unpredictably and the importance of adapting expectations.

---

5. Personal Growth and Self-Reflection

Jeff shares insights into his journey of self-improvement, emphasizing compassion for others and self-compassion.

[22:17] Jeff Hiller: "My dick is also exhausted."

[23:31] Katherine: Reflects on her own experiences with intervening in conflicts, highlighting personal growth and reliability.

[24:04] Katherine: "I have compassion for everyone, but I'm not ever compassionate to me, towards yourself."

---

6. Relationships and Emotional Maturity

The conversation shifts to the dynamics of long-term relationships, the necessity of communication, and emotional growth.

[28:28] Jeff Hiller: "You've got to work at it. You have to like, check in with people."

[29:16] Katherine: "I have to carve out that kind of time."

They discuss the complexities of maintaining a healthy relationship over time, including setting aside dedicated time and addressing annoyances constructively.

---

7. Audience Q&A and Advice Segment

The hosts and Jeff tackle listener questions, offering candid and humorous advice.

a. Rob’s Dilemma: Overwhelmed by Mother's Religious Gifts

Question Summary: Rob, a 36-year-old gay man from a conservative evangelical family, is frustrated with his mother continuously sending him Bibles and religious items despite his progressive lifestyle.

[38:03] Katherine: Suggests having a direct and gentle conversation with his mother to express his feelings.

[39:33] Jeff Hiller: "A polite, tactful way of saying, I think I'm good on Bibles is maybe enough."

b. Timothy’s Relationship Crisis in the Netherlands

Question Summary: Timothy, moving from South Africa to the Netherlands with his less emotionally mature boyfriend, faces challenges in their relationship, including poor sex life and the suggestion of an open relationship.

[41:39] Jeff Hiller: Advises focusing on communication, setting boundaries, and seeking couples therapy to address underlying issues.

[46:04] Katherine: Encourages Timothy to frame therapy as a means to improve their sex life, thereby making it less intimidating for his boyfriend.

c. Judith’s Family Complexities: Mother Remarrying a Step-Sister’s Husband

Question Summary: Judith, a 47-year-old single mom, is distressed by her 72-year-old mother marrying her stepsister's socially difficult husband, Larry, leading to familial tensions.

[62:00] Katherine: Recommends setting boundaries and asserting her feelings by choosing not to engage with Larry while maintaining a loving relationship with her mother.

[66:34] Jeff Hiller: "It's clear. Your mom has terrible taste in men."

[69:35] Katherine: "You've done the work. You got this. Don't do it. Be nice to your mother. Tell her you love her and that you're always open to seeing her. But you're not interested in hanging out with Larry."

---

8. Conclusion

The episode wraps up with reflective banter between the hosts and Jeff, emphasizing the importance of self-awareness, setting boundaries, and proactive communication in personal relationships.

[73:16] Jeff Hiller: "Thank you. Seriously, thank you."

[73:52] Katherine: Highlights upcoming performances and encourages listeners to support Jeff by ordering his book.

---

Notable Quotes:

• Jeff Hiller [05:35]: "I think that's why I'm funny now. I think that was like a self coping mechanism..."

• Katherine [14:12]: "I always had that in my head based on her success, which is so silly and so stupid."

• Jeff Hiller [22:17]: "My dick is also exhausted."

• Judith [69:30]: "I'm not a people pleaser anymore... I don't want to put myself in a situation where I'm not being real."

---

Key Takeaways:

• Resilience Through Adversity: Jeff's experiences with bullying in his youth fostered his comedic talent and personal strength.

• Flexible Success Timelines: Success doesn't adhere to a strict timeline; personal growth and adaptability are crucial.

• Importance of Self-Compassion: Being kind to oneself is as vital as showing compassion to others.

• Healthy Relationships Require Work: Open communication, setting boundaries, and dedicating time are essential for maintaining long-term relationships.

• Assertive Boundaries with Family: It's important to assert personal boundaries, even with family members, to maintain healthy relationships and personal well-being.

---

This episode of Dear Chelsea offers a blend of humor, personal anecdotes, and heartfelt advice, making it both entertaining and insightful for listeners navigating their own personal and professional challenges.

Transcript

[Chelsea Handler]

This is an I Heart podcast.

[Katherine]

Listen up. You know what's better than being a jittery mess after your third coffee? Actually functioning like a normal human being. Beyond Brew by Live Conscious is a six in one mushroom blend that won't make you trip balls, but it will give you mental clarity, focus and less bloating. Forbes called Beyond Brew a deliciously potent coffee alternative and 400,000 people can't be wrong. It comes in cacao, beautiful caramel macchiato and vanilla latte. Because we are not savages, your mind and body will thank you later. Go to liveconscious.com and use code Chelsea for 15% off let's take a quick vital break for our sponsor Vital Proteins, the number one collagen peptides brand in the US. After 30, unfortunately, your body's natural collagen production starts to dip, leading to fine lines and saggy skin. But a daily serving of Vital Proteins Collagen Peptides helps helps keep your skin hydrated and elastic. Vital Proteins is basically the secret to your youthful glow. Enter Promo code [e-mail] to get 20% off. These statements have not been evaluated by the Food and Drug Administration. This product is not intended to diagnose, treat, cure or prevent any disease who.

[Ryan Seacrest]

Needs headphones when you have glasses? Ray Ban Meta Glasses with discreet open ear speakers and built in microphones, you can play your favorite tunes. Hey Meta Play hip hop music while staying in tune with the world around you. Ray Ban Meta Glasses choose from a variety of classic Ray Ban frames, all with Meta [e-mail] AI glasses and don't forget to say hey meta play iheartradio to enjoy your favorite radio stations, artists and podcasts on the iHeart app.

[Jeff Hiller]

Hey, it's Ryan Seacrest for Albertsons and safeway now through July 15th. Stock up on all your favorite personal care brands and earn four times points to use on later purchases. For discounts on groceries or gas, shop in store or online for items like Pantene Shampoo, Old Spice, Total Body Deodorant, Tampax Pearl, Venus Razors, Head and Shoulder Shampoo, Olay Body Wash and Pantene conditioner and earn 4 times points. Hurry before these deals are gone. Offer ends July 15th. Restrictions apply. Offers may vary. Visit albertsons or safeway.com for more details.

[Katherine]

Hi Katherine.

[Chelsea Handler]

Hi Chelsea. Where in the world are you right now?

[Katherine]

I'm in London. I'm in London. I just finished Glastonbury. I still have my voice intact. I have my body parts intact. It was a wild, wild ride I'm hoping. Well, I don't know what kind of photographs are out there, but there might be some things. Got pretty. Pretty carried away, as one can imagine. And I had never been to Glastonbury before, and now I know what it's all about, and it was ridiculous.

[Chelsea Handler]

It is one of those ones you hear about always being, like, very epic, very wild, but very fun. Yeah.

[Katherine]

I usually don't like a music festival just by the nature of being outside and, like the heat and all those people. But Glastonbury just has a different ring to it. And so I had to come up and I had so many friends that are going. And so, yes, we had a wild, wild time. And let's just say I dosed a lot of people.

[Chelsea Handler]

Oh, fantastic. Fantastic. With your lsd that you're no longer traveling.

[Katherine]

I don't travel with drugs. I don't travel anywhere with drugs. I don't have drugs. I don't do drugs.

[Chelsea Handler]

She's drug free.

[Katherine]

As long as I'm in London, that's the story I'm sticking to. And my name is Chelsea Handler and I am drug free. I only like alcohol.

[Chelsea Handler]

Excellent. Well, we have a really fun guest today.

[Katherine]

I know. He's so funny. Oh, my God. You guys know him from somebody somewhere. He's hilarious. And he has a new book that's out. And his name is. Well, his Instagram name is Boom Boom Hiller. And that's what I call him during the entire episode, but his name is Jeff Hiller. Okay, we're sitting here with Jeff. I want to call you Boom Boom. Do I want to call you Boom Boom because that's your Instagram, man.

[Boom Boom Hiller]

That is my Instagram name.

[Katherine]

Okay, Boom Boom Hiller is here, everybody. For anybody who knows him on Instagram, and for those of you who know him from his hit show on HBO with Bridget Everett Somebody Somewhere, which is in its third season. Right. You're about to shoot your third season, or is it about to air?

[Boom Boom Hiller]

The third season already aired?

[Katherine]

Yeah, third season already aired. Okay. Boom Boom, otherwise known as Jeff Hiller, has a new book called Actress of a certain age. My 20 year trail to Overnight. This is a very, very, very funny book. And there's a lot of highlights. So let's get into it. First, I want to talk about your upbringing. Cause you grew up in Texas.

[Boom Boom Hiller]

Yeah.

[Katherine]

Okay. As a gay boy, man, you were yet a man. Right.

[Boom Boom Hiller]

And a little bit of a girl.

[Katherine]

Yeah. And your childhood sounded. I mean, your school experience just made me want to start a group. Like, I want to start a parenting group for parents to make sure that their children don't treat other children so horrendously. I wouldn' I wonder if there are actual parents out there that are proud of having their children be bullies.

[Boom Boom Hiller]

I mean, there's all kinds, right?

[Katherine]

That's right. Of course there are all kinds. But it's just harrowing to go through. I mean, I was bullied. I was a bully at certain points.

[Boom Boom Hiller]

Okay.

[Katherine]

I was. Yeah. Because I had to flip the switch. I was like, fuck this shit. I'm gonna be the fucking bully if you're gonna bully me.

[Boom Boom Hiller]

Oh, my God. I think I'm, I, I'm. I think I'm feeling like support for bullies now. Yes. That's so beautiful.

[Katherine]

Yeah. I need a support group for other bullies this next. Actually, that's actually what I'm trying to get. Helping me get there. But your childhood in school and the torturing or the teasing and the bullying just sounded terrible.

[Boom Boom Hiller]

Yeah, it was bad.

[Katherine]

It was, right? Yeah, yeah. I mean, and when you look back at that now, what do you think? Do you think it helped build character?

[Boom Boom Hiller]

I mean, it probably did. I wouldn't say that that's a reason to encourage it for your children, but I. Yeah, I think it did. I think that's why I'm funny now. I think that was like a self coping mechanism, you know, to try and be like, let me make you laugh so you won't hit me.

[Katherine]

That kind of a thing. Absolutely. You're like, I have to find out. Like in one scene, you're on the bleachers with somebody and you're like, why do you keep kicking me? Why? And he says it's because of the way you hold your books in school. So you were. Cause you were holding them to your chest like a little girl. And so they were making fun of you for not holding your books to the side. Like the way a strong man should hold his books.

[Boom Boom Hiller]

Exactly. And to this day, I can't hold my. I can't. If I ever hold myself like this, I'm like, oh, butch it up. You know, I have to put my hand in.

[Katherine]

Yeah, don't get a briefcase. You're gonna walk holding it to your chest looking like a real asshole, you know? Well, I mean, when they say it builds character, it's always like, you know, I remember going through high school and going through those periods of time where some girl would call me up and be like, we're going to kick the fucking shit out of you tomorrow. And you're like, my mom's like, it's okay. Everything's going to be. I'm like, it doesn't sound like it's going to be okay. And how is this character, like, sweet.

[Boom Boom Hiller]

Of your mom, though?

[Katherine]

It's like, character building. Like, I don't know how it builds character, because it seems like a nice, pat answer for when the bullying is happening, but I wonder if it really does build care. It definitely builds a resourcefulness for you to deflect, deter, and wiggle.

[Boom Boom Hiller]

Yeah. And I. And I mean, whatever. I think it's always nice to find the silver lining, but I wouldn't. It was really. I think I could have gotten sufficient character with just, you know, 80% less torture.

[Katherine]

Yeah. No, when I was reading it, I was traumatized for you. I was like, this poor kid. I was like, no wonder. I mean, no, I mean, no wonder. I don't know what, but no wonder.

[Boom Boom Hiller]

Like, no wonder you're like this.

[Katherine]

Just no wonder you're like this. Absolutely. So you grew up in Texas and you fantasized about becoming a pastor, but that wasn't gonna work because.

[Boom Boom Hiller]

Big ol homo.

[Katherine]

Yeah.

[Boom Boom Hiller]

Yeah. And I mean, like, thank God. I don't think I would have been happy being a pastor, you know, And I feel like if I had been born straight, I probably would be a pastor right now and have, like, you know, a nice life, I guess. But I think I would have not been able to perform in the way I wanted to perform. So it's good. It's good. I got to be gay.

[Katherine]

Well, you're still a churchgoer, though. You like church?

[Boom Boom Hiller]

Yeah, yeah.

[Katherine]

Which is kind of similar to your character on the show.

[Boom Boom Hiller]

Yes, yes.

[Katherine]

You're kind of pastor, like, on the show as well.

[Boom Boom Hiller]

Yeah, yeah. And that's just a coincidence. They had written that. They didn't write it for me.

[Katherine]

How funny.

[Boom Boom Hiller]

I know. Isn't that weird? Yeah, yeah, yeah. That was just a beautiful little coincidence. And I do like Jewish. I don't go every Sunday or anything like that.

[Katherine]

You don't?

[Boom Boom Hiller]

No. And my husband's Jewish, so it's not like.

[Katherine]

So there's a conflict.

[Boom Boom Hiller]

Exactly.

[Katherine]

Well, congratulations on getting a husband. See, Everything worked out for you. Okay. That's all any girl needs is a husband.

[Boom Boom Hiller]

It's true. It's all I've wanted since I was playing with my doll.

[Katherine]

The book talks about all sorts of things. It talks to you, quote, lots of different memoirs of lots of different famous people, myself included. I believe I was in there. And you also go over lots of humiliating auditions and on camera roles. So let's start with some of those. What do you think was your most. I find auditioning degrading. Also, like, I find that to be an insult to anyone's. First of all, you have such beautiful teeth. I just want to say that.

[Boom Boom Hiller]

Thank you.

[Katherine]

I'm very much into teeth and I like when they are put together. Well. And yours, I don't know if they were put together or if that happened naturally, but they're nice, you know, I.

[Boom Boom Hiller]

Just went to the dentist and the hygienist was like, there's nothing to clean. You must floss. You must actually floss. And I was so proud.

[Katherine]

God, that is something to be proud of.

[Boom Boom Hiller]

I was like, yes, give me a.

[Katherine]

Star every time I go to the dentist. She's like, oh, my God. When was the last time you were here? I was like, two fucking months ago, bitch. You told me to come every two months. And then she's like, I told you to come two months. And I don't know if she's trying to hose me. Cause she knows I'll just pay for it because I care so much about dental hygiene. But she'll be like, oh, there's a lot of plaque buildup. I'm like, that's impossible. I just got here two months ago. I haven't even eaten anything since I last saw you. How could there be plaque buildup?

[Boom Boom Hiller]

That is shocking. Sometimes I actually just left one dentist for another because I felt like the other dentist was like shaking me down. It was like every time I went there, there was something else crazy wrong.

[Katherine]

You're like, you need an X ray. It's like, do I? I'm pretty sure my teeth are set. Like, I'm not pretty sure. You're not gonna find a fucking cavity now. I'm 50.

[Boom Boom Hiller]

Exactly. But then I went to this new one and they were like, no, we still need an X ray. And I was like, oh, maybe they're all shaking us down. But to go back to auditioning, you know what? I feel like my self esteem is so low that I'm just like, I deserve to audition. So I'm like, let me dance for you. Let me dance for you, daddy.

[Katherine]

Yeah, but I mean, some of your on camera work, your early on camera work was as degrading as an audition.

[Boom Boom Hiller]

Absolutely.

[Katherine]

Let's talk about the one in the stall where you had to basically. Well, there's two scenes that I'm thinking of right off the top of my head. One is the butthole. Waxing the butthole. And then the second one was the stall, by the way.

[Boom Boom Hiller]

I don't want us to explain either of these. I just want them to be like.

[Katherine]

Waxing the butthole out there. I mean, elaborate, please.

[Boom Boom Hiller]

Okay?

[Katherine]

For our listeners, these are fun stories that are within the book, along with many other fun stories. But I'm gonna focus, obviously, on the.

[Boom Boom Hiller]

Most humiliating aspects which I truly appreciate. So I got hired to be in this sitcom that was originally supposed to be a straight woman. And they sold it to Logo. And they were like, can you just. The lady a homo? And they were like, sure. And so then one of the scenes, they were like, we wanna spice it up, make it more gay. So I was playing an esthetician, and they were like, we're gonna have you do laser hair removal on your client's butthole while you're doing this scene. And I was like, so I have to just stare at an actor's bare butthole? And they were like, he'll be wearing a modesty pouch and a modesty.

[Katherine]

And you're like, what am I gonna be wearing, a fucking face mask? Who gives a shit what he's.

[Boom Boom Hiller]

And also, a modesty pouch just covers your balls and your dick. It doesn't cover the hole. So it was just like staring into an abyss. Yes, exactly.

[Katherine]

What did you call it in your book? A chocolate Cheerio. What did you say?

[Boom Boom Hiller]

Leather Cheerio.

[Katherine]

A leather leather. I want everyone to visualize a leather Cheerio. And if you can't find one, get a mirror, put it on the ground, take your pants down and do a squat. Okay? Then there was another scene in a bathroom where you had to simulate. You were like. You're giving a blowjob, right? Yeah.

[Boom Boom Hiller]

I was hired as a gay hooker, and I was. Yeah. On my knees, giving a blowjob. I mean, you know, I wasn't actually. It was for fx.

[Katherine]

For the purposes of this story, I would like to pretend that you were actually giving a blowjob. Okay?

[Boom Boom Hiller]

I'd do anything for this job. Anything. But I just had to sit on my. Or be on my knees and hold this background actor's butt. You know, be going like this. And then I had to go, like, peek around and say my one line. And then they ended up not even using that footage. They just had me come in and do audio.

[Katherine]

Audio. They came in and having him loop the. Which ADR means audio for the movie when he's not even on camera now. And then being directed by a guy that's not the director.

[Boom Boom Hiller]

No, he was just like. Just because it was Only one line. And he was like, oh, they want it pretty flamboyant. And so I jokingly did it. The line was, that's just so wrong. Or that's just wrong. And I went like, that's just wrong. And I was, like, joking, like. Like that. And he was like, yeah, that's perfect. Thank you. And I was done.

[Katherine]

Yeah. God. So humiliating, right? I mean, this business is so fucked up. I know, it is. It's unbelievable the things that people have to go through. I mean.

[Boom Boom Hiller]

I know. But also, if that show had called me back, I would have gone in a heartbeat.

[Katherine]

Of course. Of course you would have. If they called. Yeah. I mean, you know what? I. There's not a lot to stop you. You talk a lot about, you know, achieving success and how long it's taken you, and that you would always kind of use as a barometer other people's like, when was it stupid?

[Boom Boom Hiller]

But yes.

[Katherine]

Well, it's not, because I think it's very common. You know, people have these timelines and everything. People get very rigid about when they're going to achieve certain things in their life. Like, when am I going to be successful? I remember always looking at Jennifer Aniston, that she got friends when she was 32 years old. So I related to this part of your book because I always thought, as long as by 32, if I've got my. I have until I'm 32. Like, I always had that in my head based on her success, which is so silly and so stupid. I know.

[Boom Boom Hiller]

But then I would move the line sometimes.

[Katherine]

Yeah, of course. Because you get older, you're like, why am I still fucking waiting tables? You're like, oh, my God, how long is this gonna go on?

[Boom Boom Hiller]

I know. And I was in LA for pilot season and I heard a podcast with Megan Mullally and Nick Offerman, and they were like, we both got our shows at 39, and I was 39. And I was like, I've got one pilot season left. And of course. But nobody wants to hire you when you're like, please, please hire me. I've only got this one season left.

[Katherine]

Yeah. So talk about how somebody somewhere came along. Cause that really just came right out of. Came right for you.

[Boom Boom Hiller]

It did.

[Katherine]

It's. I mean, a perfect role for you.

[Boom Boom Hiller]

I know.

[Katherine]

After reading your book, I'm like, this is kind of exactly who this character is.

[Boom Boom Hiller]

I know. And it was. Again, it was like just whatever. Fate. I have not a friend, a person. I know I write about this in the last chapter, but it's like a sponsor? No, just a frenemy I think is more the word.

[Katherine]

I'm looking for a frenemy.

[Boom Boom Hiller]

Okay, not even a frenemy, just someone I'm like, oh, what are you doing anyway? This person told me a friend that you don't like.

[Katherine]

It's a friend that you don't like. Let's just say what it is. We all have them.

[Boom Boom Hiller]

This person said to me, the reason you got your sitcom is cause your mom died. And so all of her good energy went out in the world and helped you. And part of me is like, what are you talking about? Also don't say that to people that are gonna kill their mom to get a sitcom. But I do kind of feel like there is some truth to that.

[Katherine]

Cause it does feel like you meet somebody somewhere.

[Boom Boom Hiller]

Yeah, yeah.

[Katherine]

That doesn't feel like a sitcom to me. So that's where you threw me off. That doesn't feel like a sitcom. You're right. I feel like sitcoms. I think of like multicam, live audience.

[Boom Boom Hiller]

You know, what a dream. I would have loved to.

[Katherine]

Well, for you it would be because you're gay. But for me that's like, I fucking hate that shit. And I love live audience. Cause I'm a stand up. But I like cameras.

[Boom Boom Hiller]

And like you had your own multicam.

[Katherine]

Did I? Barely. I mean it was about one of my books and then they forced me to be in it. It was just not, it was not running on all cylinders, that's for sure. That's not my world. Like I have to be real. I can't be like that.

[Boom Boom Hiller]

You know what I mean?

[Katherine]

I can't be like doing things 50 times and over, you know, like in front of a live audience. Like I find that very cheesy. There's no improvisation. Like I like to be able to improvise. So a sitcom is not for. That's not my bucket, in case you haven't fucking caught on.

[Boom Boom Hiller]

Okay, see that's what's so great about you is you know yourself so well.

[Katherine]

Don't you know yourself well at this age? How old are you right now?

[Boom Boom Hiller]

I'm 49.

[Katherine]

Okay, I'm 50. I just turned 50. So we're the same age.

[Boom Boom Hiller]

Yeah, exactly.

[Katherine]

So I would. Don't you think you know yourself really well too?

[Boom Boom Hiller]

I guess I'm not as emphatic about it.

[Katherine]

Do you think that you're actively learning new things about yourself?

[Boom Boom Hiller]

I mean, it's not as frequent that I'm learning something really shocking about myself as it was in your twenties. Or something. But, yeah, I think.

[Katherine]

What was something that you found out about yourself in your 20s that shocked you?

[Boom Boom Hiller]

Well, that I was fine with rejection. Cause I told my mom I wanted to be an actor, and she's like, oh, you could never handle the rejection. I was just like, oh, okay. And then I started doing it, and I was like, this is nothing compared to getting bullied in high school or whatever.

[Katherine]

Holy shit.

[Boom Boom Hiller]

I was like a soft ghost where they never tell me if I got it. Totally fine.

[Katherine]

Rather than getting hit in the head with a fucking Trapper Keeper. Absolutely. I would choose that any day of the week. Excuse me. I just quiet burped just for our guest. I love that Boom Boom is your Instagram name, because I call everything a boom boom. Like, when I say, lower the volume, I always go, lower it one boom boom. Like, if I'm talking to someone about a remote, I always say, oh, did you. Like, if someone farts, I go, is that a boom? Did you make a boom boom? And I mean, boom boom is applicable to, like, if my bra strap is like. Like, I'll say, like, can you, like, tighten it? Like, if they're getting me dressed, I'll say, can you tighten it one boom boom? Like, I use boom boom all the time, so I just love that that's your Instagram name. That was what first drew me to you.

[Boom Boom Hiller]

Well, I feel like when I started it, it was. Cause whenever anybody would say anything slightly sexy, I'd be like, bom bom.

[Katherine]

But then recently, you realize how unsexy that is. Yeah.

[Boom Boom Hiller]

Yeah, exactly. And also, people told me that a lot of. A lot of. When people were children, a lot of parents called taking a crap a boom boom.

[Katherine]

A boom boom. Yeah. Like, I call it a should do be. But there is a boom boom factor to that, too. I didn't want to throw your name in shit right there. I actually left that part out, but you brought it back, so good for you.

[Boom Boom Hiller]

Thanks.

[Judith]

Yeah.

[Boom Boom Hiller]

Still learning about myself.

[Katherine]

Yeah, you're still learning, so. We all are. So talk to me now about the success of being on this show for three seasons, what it means to you about your relationship with Bridget, whom I love.

[Chelsea Handler]

And of course, you guys mean Bridget Everett. Jeff stars with on Somebody Somewhere.

[Katherine]

Bridget once told me we were on the Vineyard, Martha's Vineyard, at Amy Schumer's house. And she told me one of the funniest sex stories I've ever heard, one of the most enthralling sex stories I've ever heard, and I could not ever get it out of my mind. But I will leave that to Cher on her own. But tell me about working with her. Tell me about working on the show.

[Boom Boom Hiller]

Well, I was like. I admired her. I was kind of like the character in that. I was, like, obsessed with her. I always went and saw her shows in New York and stuff. And then she just, out of the blue, emailed me and said, would you be willing to audition for my HBO show? And I was, like, temping. I was like, yeah, I guess I'll, you know, deign to do it. And I read the character, and I was like, oh, you know, this is me. I think she wrote this for me. And they were like, no, we didn't. We didn't.

[Katherine]

They didn't. No, they didn't.

[Boom Boom Hiller]

No. And so many people have told me that they also auditioned for it and.

[Katherine]

Oh, wow.

[Boom Boom Hiller]

Yeah. So. I know. I mean, it doesn't matter. I got it.

[Katherine]

Yeah, it doesn't matter. Really. We need to look forward, not in the rear view. But you used to always go see her perform, right? At her, like, Cabaret is. She performs cabaret, right? I don't wanna.

[Boom Boom Hiller]

But it's like. It's not like.

[Katherine]

She's incredible. She has an incredible voice.

[Boom Boom Hiller]

Wild and insane and funny. Really, really, really, like, legit hilarious, funny. Not like. It's not like, you know, I once heard this song. You know, it's really.

[Katherine]

Yeah. I had to go see somebody do Cabaret once, and I honestly could not believe it. Once I. I did. I went once. It was a friend, and I. I couldn't stay until the end because I couldn't face her afterward. It was just the opposite of everything that I respond to. I. That's exactly. It's exactly what you just did right there. Like this talking, slash, singing to the audience. I am not on board for that at all. I want to circle back to.

[Boom Boom Hiller]

That's not Bridget.

[Katherine]

No, that's not Bridget at all. Bridget is a force and has her own thing going. She's very unique. I want to circle back to learning more about yourself at our age, because I think I was thinking about this the other day. Like, I heard something about a friend, and I wasn't involved at all. But I'm an interloper. I like to involve myself. You know, respect. And it was an issue that I was like, you can't do that. It's bullying. It's mean to this person, blah, blah, blah. And I had overheard it, and I said I'd overheard it from some friends. I'm like, I'm gonna say something to Her I have to. And they both just kind of looked at me and went, well, it's really none of your business, but of course you're gonna do it. And I was like, because she's gonna hear it from me, and she's gonna know that it's serious. Like, if I heard this. And I was hesitant to even get involved, but I was like, no, actually, she needs to hear it from me. Cause I know she's gonna take it seriously from me rather than my group of friends that were talking to her. There's a little bit more of a dynamic between us, which is I know that she would listen. And I thought, this is exactly the kind of thing that you do, Chelsea. Like, I thought before, I was like, there was a moment of hesitation and I said, maybe you don't get involved. And I go, no, no, no. This is actually, like, important to say out of respect for all women. Like, it was one of those things. And when I did it, it was a reminder of who I am. You know what I mean? Like that. Yes, you're always gonna do that. You're always gonna do the right thing. You're always gonna be the person that says the uncomfortable thing. Because it's important not just to fucking swing my dick around. It has nothing to do with that. I'd rather not swing my dick around. My dick is exhausted. Will you name this episode my dick is exhausted with Boom Boom. I'd be happy to.

[Boom Boom Hiller]

Thank you, actually. Agree. Same. My dick is also exhausted. But I think that the moment of self reflection before you did it, that's what's important. And that's where it's growth, you know?

[Katherine]

Yeah, that's what's important. But it's also the other side of it was how reliable I am to myself and to my, like, you know what I mean? Like, I'm not gonna let things fall under, like sweet be swept under the rug. I'm not that personality. I don't like that I'm always gonna stand up when something needs to be said on behalf of a person. An underdog, a woman, whomever. You know what I mean? And I like that about myself. And sometimes it is being an interloper. But guess what? The net result was exactly what I wanted it to be. Where this woman was like, I can't believe you heard this. I can't believe I anyone said that. I can't believe I said that. I'm so embarrassed that you know about this. And I'm like, I know, but like, you can't do stuff like that. To other women. Like, it's so uncool, especially when you have a daughter, you know? So it was like one of those moments where I was really happy I did it. And I was reminded of my reliability. And I don't know why I'm bringing this up, but, I mean, I'm just talking about learning and growing with yourself. You kind of start to settle into your personality, and then while there are things you always wanna change, there are also things we should remind ourselves that we like about ourselves.

[Boom Boom Hiller]

Yes, exactly. But I think also, if you hadn't thought, wait, is this something I wanna do? Then I don't think you would've known that either.

[Katherine]

Exactly.

[Boom Boom Hiller]

And that's about the growth, too. And my big thing is I wanna have compassion for everyone. And I just made this realization recently where. And I always say for everyone. And in my mind that means, like, you know, Donald Trump or whatever. Like, you know, like, even though he is oppressive to people and groups, including groups I'm a member of, but I realized, like, I'm not ever compassionate to me, towards yourself.

[Katherine]

Yeah.

[Boom Boom Hiller]

And that was, like, a thing that I just realized about myself and think. And now I'm, like, really being active to be. Like, I've journaled for years. And when I was writing this book and I'd go back and look at my journal, I was like, jesus, I'm the most mean to my. I mean, it was just like, stupid Jeff. Like, if I found this from someone else, I would have been like, what is wrong with this person mentally? Like, why are they so obsessed with me? And I found that anyway, so that's like a thing where I'm like, okay, I'm growing. And it's about self reflection, and it's about, like, taking that little moment to be like, wait, who are you? What are you doing this for? Why are you doing this? And then you can feel good about it. Being the interloper versus, whoops, I interloped with.

[Katherine]

Yeah, I used to interlope too much. Like, when I wasn't involved and it wasn't my friends, I would be a stranger on the street. And I have a problem with that. So. But I've basically modulated my behavior. Is that the word? Is there any way we can make it a little cooler in here? Jeff took his pants off. And I am now. I feel like I'm going through perimenopause for the second time.

[Chelsea Handler]

Turn it down 1.

[Timothy]

Boom, boom.

[Katherine]

I like your mustard socks.

[Boom Boom Hiller]

Oh, thank you.

[Katherine]

I mean, I think I do. Thank you. I like that it's what was that.

[Boom Boom Hiller]

About always being truthful?

[Katherine]

I'm digesting that. But I like the outfit that you've put together. It's like an ensemble piece and I like it. I like it.

[Boom Boom Hiller]

Oh, I read on camera and I was like, make it cute.

[Katherine]

Oh, that feels so good already. Thanks, it does. I'm very specific about air conditioning. I want it. I mean, I want it. I want it all the time. I want it at night, I want it during the day. I feel like when there's not circulate, like, especially if I'm on stage, like, the theater has to be fucking col.

[Boom Boom Hiller]

Especially for to do comedy. People don't want to laugh when it's, like, swampy.

[Katherine]

Yeah, well, some people don't mind that. Some people just sit and sweat and they don't care. And you know what I call those people? New Yorkers in the summertime, just sitting and sweating and walking through this. Like, you know, there's something really gross about New York with this steam coming up in the summertime from the subways and from the sewers when it's already hot and it's just like cement mixing in the air with, like, dog shit and who fucking knows?

[Boom Boom Hiller]

Sweet home.

[Chelsea Handler]

Like, it doesn't even have to be summer. Like, I was there a couple weeks ago in the spring, like in April, and It was like 50 degrees and I'm sweating. I was just like, why is it so gross? The air is so.

[Katherine]

Well, that sounds like perimenopause, Catherine.

[Chelsea Handler]

There you go. I'm going through it.

[Katherine]

50 degrees and sweating sounds like something. How long have you been married?

[Boom Boom Hiller]

I don't know how long married, but 17 years together.

[Katherine]

17 years together. And what does your husband do for a living?

[Boom Boom Hiller]

He's a visual artist and he teaches visual art.

[Katherine]

And how did you know that he was the person that you wanted to marry?

[Boom Boom Hiller]

Well, when we got the legal right.

[Katherine]

Was he the only person that asked you?

[Boom Boom Hiller]

He's exactly my type. Willing. When we had our first date, he had volunteered at a shelter for women at a synagogue the night before, and I had volunteered at a shelter for men at a Lutheran church the night before, and it just felt too cute.

[Katherine]

That is really, really sweet.

[Boom Boom Hiller]

Yeah, it felt very, like, ordained or what have you.

[Katherine]

Yeah, I mean, two volunteers. What are the chances of that?

[Boom Boom Hiller]

Well, listen, when you're dating in New York City, it's pretty rare.

[Katherine]

Yeah, it would be pretty rare. Do you still volunteer?

[Boom Boom Hiller]

Yeah, not with that same shelter anymore, but yes, I do.

[Katherine]

Oh, good for you. I always. Yeah. I wish I were Someone who volunteered.

[Boom Boom Hiller]

Well, you can't. I mean, you can.

[Katherine]

Yeah, I could. I could. You could volunteer. Barack Obama and Michelle Obama go to soup kitchens and volunteer.

[Boom Boom Hiller]

Not every week or anything.

[Katherine]

No, they don't. But it's like a press opportunity. But it's a nice thing to do. I like to think I'm doing good things in other ways, you know, but who cares about being famous? I'm not talking about that aspect of things. And volunteering, you know, you either can volunteer or not. Really doesn't matter who you are.

[Boom Boom Hiller]

Yeah.

[Katherine]

And shout out to all the famous people who are doing it and not.

[Boom Boom Hiller]

Getting photographed and volunteering.

[Katherine]

Yeah.

[Boom Boom Hiller]

Does it even count if there's no camera?

[Katherine]

I don't know. What's something that you've learned about from being married for this or being together with someone for 17 years? What's something that you've learned about yourself? Did you know you would be this good in a relationship?

[Boom Boom Hiller]

I mean, am I good? I don't know. I mean, like, it just lasts. Cause you don't leave it. It's not like. I mean, I guess the thing that I learned is like, you do have to work at it. You do have to like check in with people. And there can be times when you're like, oh man, I. I really have been sort of neglecting my spousal duties. That sounds like oral. I mean, like, I'm not waxing his butthole.

[Katherine]

Is that what you meant to say?

[Boom Boom Hiller]

Exactly. No, just like I'm busy with my career and I'm, you know, I'm doing press for this book right now. And so like we have a day every Saturday that we is like, that's a sacred day. And we can't. If something really big comes up, we can say yes to it, but we need to like check in with the other and stuff like that.

[Katherine]

Yeah.

[Boom Boom Hiller]

And that's the kind of thing that I really would not have done.

[Katherine]

Nurtured for yourself.

[Boom Boom Hiller]

Yeah, exactly.

[Katherine]

That you would have to carve out that kind of time.

[Boom Boom Hiller]

Yeah, exactly. And that like, I kind of just thought it would all just happen organically.

[Katherine]

Yeah, I think. But it is important to know that relationships take work. You're not just gonna, you know, people have this idea, especially young dumb girls have this idea like they're gonna get married and everything's just gonna come together. And it's like you're not taking into account any of the pitfalls of a long term relationship and what can happen and all of the drama that goes. Life changes and job changes and city changes. Every relationship takes work. Even friendships take work.

[Boom Boom Hiller]

Exactly.

[Katherine]

During certain times. Hopefully it's not all work. But yeah, I mean. Right.

[Boom Boom Hiller]

And occasionally there's annoying. Sometimes I think that's a surprise, too, is that sometimes I get annoyed by him, which, of course, you get annoyed by your roommate. Why wouldn't you get annoyed by the person who's not only in your apartment, but in your bed? And you just have to think like, well, first of all, we. Cause I'm a real people pleaser. So for a lot of the beginning of a relationship, I just never said, like, it bugs me when you do whatever. And so that's the big thing that's been, for me has been like, okay, is this something that is worth saying? Do I pull a Chelsea? Do I say it? And that's been a really big learning curve, and it needed a lot of therapy and stuff.

[Katherine]

Yeah, No, I can relate to that completely.

[Boom Boom Hiller]

Oh, really?

[Katherine]

Yeah. I was surprised because I used to just pop off, and now it's more like discerning. I'm more discerning, and it's more focused and targeted.

[Boom Boom Hiller]

Right. And I used to just suppress.

[Katherine]

Right. I would now know I have the opposite. Explode, explode, explode. You're suppressed. Suppressed. We're opposite. Do you know what number you are on the Enneagram? Do you know what an Enneagram?

[Boom Boom Hiller]

Three wing two.

[Katherine]

Oh, okay. Three wing two. I'm in.

[Boom Boom Hiller]

Or it might be a two wing three. Oh, yeah, that's like. Oh, yeah. That makes total sense. I'm just getting into the Enneagram, and I love it. But, you know, when I first found out, I was a three in college, when I was in my Christian college, I took a class called Vocations and Voices, and our campus pastor gave us the Enneagram test.

[Katherine]

Wow. Really? Is that surprising? Yeah, that sounds like modern. Very modern. Because I feel like the Enneagram is like a new thing. I mean, but I don't know why I think that.

[Boom Boom Hiller]

Well, it was at least around in 1993 or four.

[Katherine]

It was. That's when the Internet was invented by Al Gore. 1994. Do you remember that?

[Boom Boom Hiller]

Yes, I do. Thanks, Al.

[Katherine]

We're going to take a break, and we'll be right back with Jeff Hiller. This is an ad by BetterHelp. Workplace stress is now one of the top causes of declining mental health, with 61% of the global workforce experiencing higher than normal levels of stress. To battle stress, most of us can't wave goodbye to work, but we can start with a focus on wellness. Taking time to soak up the sun even for a few minutes during a break in your workday. Finding your center by focusing on your breath and having a coffee date with a friend are just some of the ways you can begin to refocus on your mental health. With over 30,000 therapists, BetterHelp is the world's largest online therapy platform, having served over 5 million people globally. As the largest online therapy provider in the world, BetterHelp can provide access to mental health professionals with a diverse variety of expertise. Our listeners get 10% off their first [e-mail] DearChelsea that's betterhelp.com DearChelsea Listen up guys. You know what's better than being a jittery mess after your third coffee? Actually functioning like a normal human being. Beyond Brew by Live Conscious is a six in one mushroom blend that won't make you trip balls, but it will give you mental clarity and focus to get through your day. Thanks to mushrooms like cordyceps and Reishi. Beyond Brew also has pre and probiotics so you'll feel less bloated and avoid seven trips to the bathroom every day. I love it because you can put it in your coffee or just mix it into hot water or milk. It also tastes great in smoothies. Look, Forbes called Beyond Brew a deliciously potent coffee alternative and 400,000 people can't be wrong with barely any caffeine. It won't have you crashing midday and at just 20 calories per serving, you'll get all the benefits and none of the guilt, unlike going to your favorite coffee chain. Plus, it comes in cacao, caramel macchiato and vanilla latte because we are not savages. Trust me, I genuinely feel better after taking this stuff. Your mind and body will thank you later. Go to liveconscious.com and use code Chelsea for 15% off this July 4th.

[H]

Celebrate freedom from spills, stains and overpriced furniture with Anabia, the only machine washable sofa inside and out. Where designer quality meets budget friendly pricing. Sofas start at just $699, making it the perfect time to upgrade your space. Annabe's pet friendly stain resistant and interchangeable slipcovers are made with high performance fabric that's built for real life. You'll love the cloud like comfort of hypoallergenic high resilience foam that never needs fluffing and a durable steel frame that sleeves stands the test of time with modular pieces you can rearrange anytime. It's a sofa that adapts to your Life. Now through July 4th, get up to 60% off site [e-mail] Every order comes with a 30 day satisfaction guarantee. If you're not in love, send it back for a full refund. No return shipping, no restocking fees. Every penny back. Declare independence from dirty outdated furniture. Shop [e-mail] Offers are subject to change and certain restrictions may apply.

[Katherine]

Let me switch gears for a second and talk about one of our favorite sponsors, Vital Proteins. They're the number one brand of collagen peptides in the U.S. if you're wondering what collagen peptides are, they're essentially the key to maintaining a youthful glow. After 30, your body's natural collagen production starts to dip. And that can lead to lines, saggy skin, and joints that don't move like they used to. In other words, looking old. But Vital Proteins helps fill that gap. A daily serving keeps your skin healthy, hydrated and elastic. It even supports your hair and nails. And because it's unflavored, you can mix it with anything. So your smoothie supports your skin, your coffee helps your skin, and your chocolate milkshake keeps your hair looking thick. Go ahead and get some vital proteins. You can get 20% off by visiting vitalproteins.com and entering promo code Chelsea at checkout. These statements have not been evaluated by the Food and Drug Administration. This product is not intended to diagnose, treat, cure, or prevent any disease. And we're back with Boom Boom Jeff Hiller. He is the author of his latest book. Well, his only book exactly. It's called Actress of a certain my 20 year trail to Overnight Success. Let's put him on the New York Times bestseller list. Okay, got guys. Let's all make sure we order a copy to support him. And how funny this book is because I read it. You're gonna laugh. It's worth it. We all need something to escape. And we all need to be laughing a lot more as far as I'm concerned. Okay, we're gonna take some callers and we're gonna give advice. Okay?

[Boom Boom Hiller]

Yeah.

[Katherine]

Katherine, what do we have in store for us?

[Chelsea Handler]

Well, I love that you called him Boom Boom Jeff Hiller. Like the Jeff is in quotes. That's my favorite.

[Katherine]

Yeah, for me, the Jeff is in quotes. It's actually Boom Boom Hillary.

[Chelsea Handler]

Well, our first question comes from Rob. He says, help. I'm a liberal gay man and my mom won't stop sending me Bibles. Dear Chelsea, I'm a 36 year old gay man who's been out and proud for 14 plus years. I come from a very evangelical, Republican, Midwestern family and I'm the polar opposite of them all. I still identify as Christian, but in a more New Agey, spiritual way. I can count on one hand how many times in the past decade I've seen the inside of a church and it was probably for a wedding or a funeral or because it's my polling place and I was voting blue down the ballot. I'm super progressive and my family knows this about me as I'm extremely outspoken about it. Overall, they've been very loving and accepting of who I am. They've really come a long way. However, my mom especially continues to shove religion down my throat. I have more Bibles than I possibly know what to do with yet. For my last birthday, she sent me another one. I wanted to be like, thanks, Let me just go add this to the stack of other Bibles you've sent me over the years. A couple of years ago for the fourth of July, she sent me a bunch of Americana shit to put around my house, including but not limited to a red, white and blue cross that says God bless America. Barf. Basically any opportunity she gets, she sends me some Christian crap that I don't need or want. It doesn't help that she works at Hobby goddamn Lobby and gets a discount. I know she's coming from a loving place and means well, but I swear to God, if I get one more effing Bible or Christian knickknack in the mail, I'm going to scream. Please help, Rob.

[Katherine]

First of all, why are people sending Bibles? Like, is there new information coming out in the Bible? Is there a new edition or something?

[Boom Boom Hiller]

I think for certain Christian folks, like a different. There might be a different translation or have like a nice cover or like.

[Katherine]

What are we translating it from? What language was it originally written?

[Boom Boom Hiller]

Hebrew is the Old Testament, Greek is the New.

[Katherine]

Okay. Hebrew and Greek, okay. Yeah, I feel like Bibles are wrapped. You know what I mean? Like, it's enough. We get it and they're out there. There's enough out there. We don't need to be re interpreting them. It's like, stop it with this. First of all, you have to have a very direct conversation with your mother. I would say she's obviously a Bible thumper and she's gonna be very upset that you don't want this. So you have to think of a very gentle way to just say, I'm up to my ears in fucking Bibles and I need you to back up, but I do think it's worth saying that too. What do you think? I mean, you come from a religious background. I don't.

[Boom Boom Hiller]

It's true. And I'm also, like, from the cause. My mom also was very much into church and stuff. And I think the more important thing is that she's supportive outside of the gift giving section, which I think is sort of. Obviously, probably really difficult for her. And beautiful that she does that. But I think that what you're saying is right. A polite, tactful way of saying, I think I'm good on bibles is maybe enough. But if she sends you fourth of July stuff, like, I don't know, you know, sometimes people just. You get a gift from your nana and you're like, this is not something I'm ever gonna.

[Katherine]

Maybe you could just collect all of her stuff and give it to someone like that. You know, like someone in your neighborhood, like, re gift it, drop it off in front of someone's house who you know will appreciate it. And then you take the conversation. You, you know, I mean, it's worth having a conversation anyway, because I don't think your mom's gonna listen. She's gonna probably. It will probably like, tamp it down a bit, all of the things you're getting, but she'll probably continue to send. If she works at Holly Lobby, like, it sounds like you're gonna get gifts regardless.

[Boom Boom Hiller]

That's her type or taste.

[Katherine]

Yeah. So you're gonna have to think of a way to like repurpose her gifts, you know what I mean? So that you can deal with it head on, but then also deal with the reality that you're gonna continue to get those gifts. Because mothers don't really listen to their children. Exactly.

[Boom Boom Hiller]

And is this an issue that you're willing to have of like a knockdown, drag out, fight for?

[Katherine]

No, it's not like that. This is a light question. We don't have to. Of course it's not so serious, but it is annoying to. I mean, I would be pissed if I were getting this, but I didn't grow up in a religious background, so I have no history of this. So I would be pissed. Cause it would be coming out of the fucking blue.

[Boom Boom Hiller]

It would be as much confused as pissed.

[Katherine]

I mean, oh, my God, I just love the idea of me opening up a Bible. Even in hotel rooms when I see one. I'm annoyed.

[Boom Boom Hiller]

I'm like, why?

[Katherine]

Don't push that on me? But yeah, it's not a serious situation. But you should. You can Say something to your mom Absolutely offhandedly.

[Chelsea Handler]

I wonder if you could say, like, that one you sent me for my last birthday was my favorite. I don't need any more options.

[Katherine]

Like, yeah, I don't need that. That's like a mislead. And I don't think that works with religious people indirectly.

[Chelsea Handler]

Yeah, that's probably true. All right, Rob. Well, Brett, do we have Timothee Chalamet? Yes. Okay, great.

[Katherine]

He calls in every week. It's like. And it's always about Kylie Jenner. It's so embarrassing.

[Chelsea Handler]

Every week.

[Katherine]

And it's like how she heard about this at all, yet it's amazing.

[Boom Boom Hiller]

He's always just like my girlfriend.

[Katherine]

Do you believe that those two are together? When you see Timothee Chalamet and Kendall.

[Boom Boom Hiller]

Jenner, Is it Kendall or Kylie?

[Katherine]

I don't know.

[Chelsea Handler]

Kylie.

[Katherine]

It's Kylie. Oh, never mind that. We'll get back to that.

[Chelsea Handler]

We'll get back to that.

[Katherine]

We have a caller. I can see. We're so sorry we got sidetracked with gossip.

[Boom Boom Hiller]

Talk about Timmy.

[Chelsea Handler]

Well, Timothy said his subject line is open relationship or breakup. Dear Chelsea, my boyfriend of a little over a year and I recently moved to the Netherlands from South Africa. Our sex life has never been great, but we really love each other and we make a great team. Although recently we've been having lots of disagreements, the move and adapting to a new country has understandably put a lot of pressure on the relationship. I'm generally a happy person and I'm committed to self improvement etc, but my boyfriend is not on the same page with me about that. I recently started to feel like we're not on the same page regarding our personal growth and emotional maturity in general. My boyfriend brought up the option of trying an open relationship, which I'm happy to do because our sex life is basically non existent. Although this could be really good for us, I also feel like it could be the beginning of the end. All of these things have made me think about the future of our relationship and if I want to continue with it at all. What makes things even more tricky is that I moved over on his visa, so I'm pretty sure I would have to leave the country if we brought, which would suck because it wasn't easy to get here in the first place. I love him dearly and he's very important to me, but I feel like he needs to do a lot of growing and I don't know if I should be a part of that. Please help Timothy.

[Katherine]

Hi, Timothy. This is our special guest today. Jeff Hiller.

[Boom Boom Hiller]

Hi.

[Katherine]

Hi. You can call him Boom Boom.

[Timothy]

Boom Boom. Great.

[Katherine]

That's another thing I call boom booms. Penises. I always go, oh, look at. He's got a. Or I'll say to a friend, like, if I. I'll be like, did he have a nice boom boom? So boom boom is just a great word for everything.

[Boom Boom Hiller]

I think it really is.

[Katherine]

So, okay, what are you thinking in terms of if this relationship. It sounds like this relationship is coming to a head, and that's okay. But I just want to talk about your, like, actual logistics, like, for living. Like, if you guys do break up, what are you prepared to do? Are you gonna go back to South Africa? Like, if that. If. If this is a real conversation, then we should be talk about those things.

[Timothy]

Yeah. So I wasn't exactly sure how it worked because I. I moved over on his visa, so I did of digging. So it does seem like if we break up, then I wouldn't have any other choice but to go back to South Africa. Unless we find some way to work around that. But legally, that is what will have to happen.

[Katherine]

Are you guys legally married?

[Timothy]

No, no, no. We're just like, dating.

[Katherine]

And you can bring somebody over on your. On your visa if you're dating them?

[Timothy]

Yes. Yep.

[Katherine]

Okay.

[Boom Boom Hiller]

That wacky eu.

[Katherine]

What about. And then is moving back to South Africa an option? Like, how do you feel about that?

[Timothy]

I'm not crazy about it because, I mean, I obviously sold all my stuff there, used all my savings and everything to move here. It's. It was very stressful. We just kind of like, rebuilt our life and like, create a little home here. So. So. And we were looking forward to like, traveling because it's so much easier to travel when you're in. Live in Europe. And I found a job here was. Which is also not very easy for.

[Katherine]

Okay, so.

[Timothy]

Yeah.

[Katherine]

So ideally, you want to stick around there. Is your boyfriend open to, like, couples counseling? He.

[Timothy]

I'm trying to get him to just see a therapist himself, but he is not very open to the idea I keep bringing up because I've been in therapy for like 10 years, so I know the benefits of it, like, and I know he needs it. Like, the other day he asked me something in shame. Bless him. He's very sweet. But he asked me, do you think trauma from your childhood plays over into your adult life? And I was like, yes. That's like, exactly what happens.

[Katherine]

Yeah.

[Timothy]

So he's. He's not really. He hasn't been in therapy, so he doesn't know the Benefits from it.

[Chelsea Handler]

Is he younger?

[Timothy]

He's only three years younger than I am, but I feel like there's quite a difference in emotional maturity between us.

[Katherine]

Is he someone who would read a book? Like if you brought home a book based on child, like, about the question he asked you and said, oh, I found this at the bookstore. Here's a book on childhood trauma. I thought you might be interested in this. Do you think he would read that? That?

[Timothy]

Yeah, I could try that. Like, I read a lot of self help books. So then he, it kind of caught on with him.

[Katherine]

Oh, well, that's something. That's not nothing.

[Timothy]

Yeah, yeah, yeah, for sure. No, he's definitely like looking into himself a little bit more. But like, I, I don't really want to. Like, leaving him is not really what I want to do. I really do love him.

[Katherine]

So then don't. So then don't. You're not there. You're not there yet. And, and right now I think what you should focus is on like, what do you, how do you feel about open relationships? What's your like?

[Boom Boom Hiller]

Well, I, I mean, I feel like as long as both partners are into it, which it sounds like you are, then why not?

[Katherine]

I mean, I think it sounds like.

[Boom Boom Hiller]

You define your own relationship.

[Katherine]

Right. I think it sounds like an opportunity for him to grow up a little bit too, having an open relationship. Because when you have an open relationship, like, what I would suggest is creating, like to have parameters and have boundaries and have an understanding about how much information you both want, how much information you both need. Those kinds of adult conversations are going to lead to more intense conversations about emotions and about. And like, even though you're a little bit farther along on like an emotional maturity level, it's good to, as a practice, have conversations like that where you're including him, like you're introducing a subject matter, like, okay, what are the rules gonna be? How are we gonna feel? What if I feel emotionally left out? Is it okay for me to come to and say, actually I don't feel comfortable with this? Like, you can have adult conversations that kind of pull him into a more mature position. Do you know what I'm saying?

[Boom Boom Hiller]

And the boundaries that you set at the top don't have to necessarily be constant. You know, you can say like, oh, actually I thought I was okay with that thing, but I'm not, or whatever.

[Katherine]

Yeah, like, it's actually like this whole open relationship thing is actually an opportunity for you to have more time, depth within your relationship. So I would say that, that to go for it. I mean, you're kind of at your wits end. I. Ideally what you want to do is get him into therapy so that he can start having some real conversations. But until that can happen, I would really share the books you're reading. I would share the topics that you're, that you're interested in. Like the, the things that you're reading about self help or childhood trauma. And not in a patronizing way as a way to like bounce it off of him. Like, what do you think about this? I. I'm not sure I agree with this. Do you agree with this? What do you think about this? You know, just try to engage him a little bit more in what you're interested in. And even if he's not there yet, just introduce the subject matters, you know what I mean? So there are catchphrases he's heard. Childhood trauma, does that roll over into your adult life? Like that's good that he said that sentence, regardless of whether he understands it a hundred percent.

[Timothy]

Yeah, fair enough. Just on the open relationship thing, I have a little bit of an update. After going back and forth, he actually told me, so he wants to try it. This was like two weeks ago. So we were like, yeah, cool, let's go out. Let's go try it. Let's go have fun. So we, we went to a few bars in Amsterdam and towards the end of the night, we were both standing kind of outside and then this really attractive guy came up and like just fully kissed me on the mouth. And it lost its four for like one and a half seconds. And then I pushed him away because I knew this was going to be a problem. And I looked over at my boyfriend and he was not even looking at me, didn't speak to me. And then on our way home, he was just like, I can't do this. I can't handle you being intimate with anyone else than me. Like, then it was just such a. It's such an been such an emotional roller coaster from him being on board with it and then not, and then yes and then no. So currently it's no, but I feel like it's gonna come up again at some point.

[Katherine]

Yeah, but these are also opportunities to have more conversations around the subject matter of having an open relationship. Talking about boundaries, talking about intimacy, talking about what doesn't feel right. Like, would it feel better if you weren't kissing someone if you were just having sex with them? Like really introducing all of these. Cause the more you can get him talking, the more that he's gonna open up emotions. And I know it's not your job, but if you're in this relationship and you're committed to staying in the Netherlands, then you kind of have to make this effort.

[Boom Boom Hiller]

But I would also say, like, being in a relationship that's not right is not worth not moving back to South Africa.

[Chelsea Handler]

Yeah. Maybe see if there's like another plan you can do with your work if there. Even if it takes a little bit of time just to have that as sort of a backup plan.

[Timothy]

Yeah.

[Katherine]

I mean, you've got one foot out the door, you know, I mean, clearly. So I know it's not a desirable place to be, but I would say to exhaust all your hours efforts before you shut the door for obviously multiple reasons, and one of those being geographic.

[Timothy]

Yeah. I think we have had a problem of just being honest with each other, having honest conversations, saying how we feel, and that's only recently been really talked about. So. Yeah, it's a lot of things that we're going through at the moment, but our sex life is like. Like a. It's been a problem for a while.

[Boom Boom Hiller]

So how long have you been together?

[Timothy]

Only a year and a half. But it's been like a problem kind of from the beginning.

[Katherine]

What's the problem?

[Timothy]

So the problem is mostly with me. I've kind of like lost my physical attraction towards him. Like, I really love him. There's no doubt in my mind about that, but I just can't get that physical attraction back. And I feel really guilty about it. And every time, like, I can see him trying to, like, you know, engage, I. I feel really guilty and I feel bad, but I don't really know what to do about it.

[Katherine]

Can you actually physically have sex with him or you can't?

[Timothy]

I really don't want to.

[Katherine]

Okay. I don't mean to laugh, but I mean, it really sounds like you're not in this relationship anymore. It sounds. Sounds like it's your friend.

[Timothy]

I know, it feels like. Yeah, it does feel like that.

[Katherine]

Okay, let me ask you, is he. Where is he in your relationship? Like, if you said like, okay, this is our last ditch effort. I'm not feeling it. We're not feeling it. We're not in sync. I really want us to go to therapy as our kind of, like, last effort. What would he say to that?

[Timothy]

I think he would. He might be open to it. I just wanted him to, to go to therapy first a little bit. Just so you can.

[Katherine]

Yeah, but don't make it about him. Make it about you. The only way to get to go to therapy is to make it about you. You have a problem with your sex. That's a perfect thing. Like, hey, I'd love to figure this out. He knows that you're having trouble with sexually. Right. He's part of this equation. Right. And so.

[Boom Boom Hiller]

Yeah, and couples therapy can demystify individual therapy. So it might actually be a perfect way to introduce them to.

[Katherine]

Oh, that's extra excellent. Yes, very well said. That's exactly right. You know, you get in there because it's your problem. Like, I want to work on our sex life. I know this is my. My issue, you know, take responsibility. And then that becomes like less of a. Less intimidating for him to go into a therapy session when you're framing it that it's more about you.

[Timothy]

Yeah, that's a very good idea. I think that's a good idea.

[Katherine]

And then hopefully that can lead into single therapy, like Jeff said, you know, hopefully with his exposure to therapy, he'll like it. So I think your job is to find a couple, get him to agree to that. Try to tell him that you really wanna work on your relationship and that, you know, you're aware of the issues. You were gonna have an open relationship. Now you don't want to. He's got jealousy issues. Okay, that's fine. You're gonna respect all of it. But you do wanna work on your relationship, even from a sexual standpoint, you know, starting there so that you can get him into therapy and. Yeah, and then start with that.

[Boom Boom Hiller]

Also, it's just. It's so much easier to have a third person there to help you discuss things like, I'm no longer attracted to you. That would be very difficult to bring up to someone who you're no longer attracted to.

[Timothy]

No, it's horrible to bring up.

[Katherine]

It doesn't have to be a permanent thing. You might just not be attracted to him right now. You know what I mean? If you build this relationship back, there's always people that come back from this that can have sex after periods of not having sex. So I wouldn't look at it as like a final thing. Like, this is not your final act, but put in an effort to salvage the relationship.

[Timothy]

Okay, I'm going to do.

[Boom Boom Hiller]

Do that and get a couple's therapist who's certified in sex therapy. There's a special certification.

[Katherine]

It's very helpful. Good to know.

[Chelsea Handler]

I also think it's a little bit of a shortcut. If you find. If you're able to find a queer therapist. Just so, like, there is a shorthand there.

[Boom Boom Hiller]

Do they have those in Amsterdam.

[Timothy]

I. I haven't heard good things about therapists in. In the Netherlands. Apparently they're not very. Not great. But, I mean, we can always do it like zoom.

[Chelsea Handler]

Yeah.

[Timothy]

Virtually.

[Katherine]

Yeah. Yeah, you could do it. Exactly. So who cares about that? You can do it over zoom with someone in New York or LA or London or somewhere where there's better therapists. I didn't. Isn't there. Aren't there a lot of therapists from the Netherlands?

[Boom Boom Hiller]

I thought so.

[Katherine]

Or Psycho. Well, I guess those are from, like, the 18th century, so who gives a shit? We've had to update.

[Chelsea Handler]

They're dead.

[Timothy]

Maybe everyone has been. People love to say negative things about the Netherlands, like, the doctors are terrible, the therapists are terrible, and blah, blah, blah. So who knows? Maybe it's all just like.

[Boom Boom Hiller]

Yeah. Yeah.

[Katherine]

Okay. Well, I mean, I hope we helped you. I mean, I don't really feel like we did.

[Chelsea Handler]

Did you check back with us?

[Katherine]

Yeah. Why don't you have that conversation with him and try and nail down a couple's therapist, you know, even if it's in the States, just so you guys can start having more conversations. And I would say one thing is, I understand. You're more. You're farther along in your spiritual journey. Don't judge him so much. Try not to try to flip the switch in your head and think of him as, like, that's an opportunity to actually teach and for him to learn more. Like, you can be a party to that. You can be, like, part of his exposure to different things, but not in a condescending or patronizing way. He is your equal. You're in a relationship. You can't be superior to him because you're more emotionally mature. You kind of just have to look at him like he has a different set of circumstances and a different history, and you're both in the same place at the same time. So, like, how can you help each other grow and how can you help each other learn? And that goes for your growth and your learning, too.

[Chelsea Handler]

Yeah.

[Boom Boom Hiller]

Because judgment is a real boner killer.

[Katherine]

But take those first steps and hit us back and let us know what happens.

[Timothy]

Okay, I'll do that.

[Katherine]

Okay.

[Chelsea Handler]

All right, Timothy.

[Katherine]

Thanks for calling in, Timothy.

[Timothy]

Thank you, guys.

[Katherine]

Okay, bye. That made my boner go down, that call.

[Chelsea Handler]

That's tough when you just aren't attracted to someone anymore.

[Katherine]

Oh, fuck, no. I feel like that's the end of the road. But there are stories about people who have completely lost their boners, so to speak, for their spouses, and then reclaimed them.

[Boom Boom Hiller]

Well, I think what you're saying about having that judgment of you, it really is. It builds up this resentment and this sort of not interest. And so that will kill your sex drive too, for that person.

[Katherine]

Especially if you're thinking someone, someone is stupid or they're not as smart as you are or spiritually advanced as you are. Like, you get into tricky territory. It's like you can be like a spiritual narcissist. You know what I mean?

[Boom Boom Hiller]

Oh God, what a coined term.

[Katherine]

Okay, we're gonna take a break. I'm gonna boom, boom, boom, boom and then we're gonna be back. Listen up guys. You know what's better than being a jittery mess after your third coffee? Actually functioning like a normal human being. Beyond Brew by Live Conscious is a six in one mushroom blend that won't make you trip out balls, but it will give you mental clarity and focus to get through your day. Thanks to mushrooms like cordyceps and Reishi. Beyond Brew also has pre and probiotics so you'll feel less bloated and avoid seven trips to the bathroom every day. I love it because you can put it in your coffee or just mix it into hot water or milk. It also tastes great in smoothies. Look, Forbes called Beyond Brew a deliciously potent coffee alternative and 400,000 people can't be wrong. With barely any caffeine, it won't have you crashing midday and at just 20 calories per serving, you'll get all the benefits and none of the guilt, unlike going to your favorite coffee chain. Plus, it comes in cacao, caramel macchiato and vanilla latte because we are not savages. Trust me, I genuinely feel better after taking this stuff. Your mind and body will thank you later. Go to liveconscious.com and use code Chelsea for 15% off this July 4th.

[H]

Celebrate freedom from spills, stains and overpriced furniture with Anabe, the only machine washable sofa inside and out. Where designer quality meets budget friendly pricing. Sofas start at just $699, making it the perfect time to upgrade your space. Annabe's pet friendly, Stain resistant and interchangeable slip covers are made with high performance fabric that's built for real life. You'll love the cloud like color, the comfort of hypoallergenic, high resilience foam that never needs fluffing and a durable steel frame that stands the test of time with modular pieces you can rearrange anytime. It's a sofa that adapts to your Life. Now through July 4th get up to 60% off site wide. @washablesofas.com every order comes with a 30 day satisfaction guarantee. If you're not in love, send it back for a full refund. No return shipping, no restocking fees. Every penny money back. Declare independence from dirty outdated furniture shop [e-mail] Offers are subject to change and certain restrictions may apply.

[Katherine]

Let me switch gears for a second and talk about one of our favorite sponsors, Vital Proteins. They're the number one brand of collagen peptides in the U.S. if you're wondering what collagen peptides are, they're essentially the key to maintaining a youthful glow. After 30, your body's natural collagen production starts to dip and that can lead to lines, saggy skin, and joints that don't move like they used to. In other words, looking older. But Vital Proteins helps fill that gap. A daily serving keeps your skin healthy, hydrated and elastic. It even supports your hair and nails. And because it's unflavored, you can mix it with anything. So your smoothie supports your skin, your coffee helps your skin, and your chocolate milkshake keeps your hair light, looking thick. Go ahead and get some vital proteins. You can get 20% off by visiting vitalproteins.com and entering promo code Chelsea at checkout. These statements have not been evaluated by the Food and Drug Administration. This product is not intended to diagnose, treat, cure or prevent any disease who.

[Ryan Seacrest]

Needs headphones when you have glasses? Ray Ban Meta Glasses where style meets cutting edge tech. With discreet open ear speakers and built in microphones, you can play your favorite tunes.

[Chelsea Handler]

Hey Meta.

[Ryan Seacrest]

Play hip hop music and tune in to the world around you. But listening is just the beginning because you can stay in the moment while your phone stays in your pocket as Meta AI provides answers to questions on the fly.

[Boom Boom Hiller]

Hey Meta, what's the weather tonight? Tonight will be clear with temperatures ranging.

[Ryan Seacrest]

From capture and share moments.

[Boom Boom Hiller]

Hey Meta. Post this video on Instagram.

[Ryan Seacrest]

You can even get Meta AI to make recommendations based on what you're looking at.

[Katherine]

Hey Meta, what can I make for.

[Ryan Seacrest]

Dinner with what's in the fridge?

[Boom Boom Hiller]

You can make a delicious spinach and chicken salad or add the baby spinach to pasta with some garlic shrimp.

[Ryan Seacrest]

Cool Ray Ban Meta Glasses choose from a variety of classic Ray Ban frames all with Meta [e-mail] AI glasses and don't forget to say hey Meta. Play iHeartRadio to enjoy your favorite radio stations, artists and podcasts on the iHeart app.

[Katherine]

And we're back with Boom, boom. In quotes. Jeff Hiller.

[Chelsea Handler]

Well, our last caller today is Judith and she has one of my favorite subject lines I've ever seen in our email inbox. It is, my mom married her dead stepsister's husband and now I have an uncle Daddy.

[Katherine]

Wait a second. My mom married again.

[Chelsea Handler]

My mom married her dead stepsister's husband and now I have an uncle.

[Katherine]

Dad.

[Chelsea Handler]

Daddy. So she says, this is a long one. Buckle up. But it's a real journey.

[Katherine]

Just a stepsister's husband.

[Boom Boom Hiller]

Yeah, it's not like she.

[Katherine]

Why does she have an uncle daddy? Oh, because it's her stepdad. Yeah, that's her uncle. Okay, this isn't the worst news. Okay. No, no, no. Okay.

[Chelsea Handler]

Judith is. Dear Chelsea, I'm Judith, a 47 year old single mom. Despite life surprises, I strive for purpose and gratitude daily. I have one issue I can't get over and I thought I'd email it. You the one person who'd tell me if I'm being a stubborn asshole. My 72 year old mom just got married for the fourth time. While multiple marriages don't faze me, it's her taste in men that's the problem. I know you're like, isn't one of them your dad? Yes, he was. He was a volatile addict. Her second was a jackass. Her third was a paranoid hoarder. In 2019, she retired and became single finally and went to live with my sister. When the pandemic lifted, she had the idea of driving around the country in a customized van to explore the world, a hippie at heart. We told her to go for it, make the most of her life. About seven months into her vagabond journey, she stopped in Mississippi to attend her stepsister's funeral. She reconnected with this side of the family and decided to stay an extra week. This is where things get weird. She begins talking about her stepsister's husband a lot. Larry this, Larry that. Here's the thing. Larry has been our uncle our entire lives and he sucks. He is one of those military guys who yell, talks, knows everything, and is outright socially belligerent. I didn't like him when I was 4 and I don't like him now. After a couple months, my mom tells us she's going on a cross country train ride with Larry. I sarcastically joke, what are you banging Larry now? She stammers. I want to vomit. This is six months after her stepsister has died. You know, the one who was Larry's wife for 47 years. They were together since high school. Six months later, she moves in with him. And a few months after that, she announces she's marrying him. In an email to us, she says, there's not a wedding. They're just going to to the justice of the peace. The next day, we wake up to a Facebook post. They're standing under a tree. She had a bouquet, a new dress. His family was there. We were not invited. Here's my predicament. Last week, she asked if they could come visit. This means her and Larry. I am the only sibling who hasn't spent time with them. Two of them tolerate him. The other has tried it and is done trying. The idea makes me rage. I want to say no. I want no part of him in my life. Am I being too stubborn? Chelsea? What do I do about my uncle? Daddy? Judith.

[Katherine]

Hard no. Hard no. Hi. Hi.

[Judith]

How are you?

[Katherine]

How are you? This is our special guest. Jeff Hiller is here today.

[Boom Boom Hiller]

Hi, Judith.

[Katherine]

Hi.

[Judith]

I totally know who you are. I'm a huge fan of your show.

[Boom Boom Hiller]

Oh, thank you.

[Judith]

So you're a no.

[Katherine]

Yes. I would say a hard no. I. Listen, I'm of the belief at our age. You're 47. I'm a few years older than you. Jeff is 49. We don't have to tolerate this kind of bullshit anymore. I don't want to be around people I don't want to be around. I have earned the. I have extended my generosity for years leading up to this point and tolerated people that I don't have to tolerate in my family and outside of my family. And I'm just. I'm not really willing to do that anymore. And I don't think there's anything wrong with it. It's creating a healthy. Who wants that guy in their house? Fucking yell talking at me. No, no, you already stated that your mother and then. And your mother is kind of has been kidnapped by him, basically. Right? Mean, so she's been hijacked by this man. And while that sucks, and I know you love your mother, you can easily say, I want to see you, but I don't want to see him. And so if you ever want to see me alone, let me know. But I'm not really interested in hanging out with Jeff, my uncle, as my father.

[Chelsea Handler]

Or Larry.

[Katherine]

What do you think?

[Judith]

Or Larry, whatever the hell we call him.

[Katherine]

Larry. Sorry, I got confused with Jeff. What did I do? Sorry. Jeff knows what he did. Jeff knows what he's done. Okay.

[Boom Boom Hiller]

I know what I did. No regrets. You know, I have this like. Okay, and again, go.

[Katherine]

No, no. Go for It.

[Boom Boom Hiller]

You know, people walk over me sometimes, so grain of huge salt. But my thought is, okay, it's clear. Your mom has terrible taste in men. And I have. I don't have family, but I have good friends who have tried.

[Katherine]

Truly.

[Boom Boom Hiller]

Just shitty taste in men. And I'm wondering if you could just say, like, you know, I'd love to see you, and I'll go to dinner with Larry, but I can't have him staying in the house. Is that enough? Or you think, no, just across the board. Don't come at all?

[Katherine]

Well, no, I mean, I think anything's an option. I think this is what, you know, this is why you're here. You have your point of view.

[Boom Boom Hiller]

Well. Cause I just feel like, you know, I got a dead mom, and I just feel like. I don't know, if you could have.

[Katherine]

Hung out with your mom and a big asshole with her, you're saying that you would have done that?

[Boom Boom Hiller]

Ding, ding, ding.

[Katherine]

All the time.

[Boom Boom Hiller]

I just feel like this could possibly create, you know, a rift, but I.

[Katherine]

Feel like that rift has been created already. Right.

[Boom Boom Hiller]

And not by you.

[Katherine]

By her. Yes. No.

[Judith]

You all are. I feel so validated right now because literally, what the both of you are saying is what my friends and family around me are saying. Chelsea, I'm 100% with you. In fact, I've used the word kidnapped multiple times. I'm like. It's like he stole our mom from our family because he needs. Needed a replacement.

[Katherine]

Yeah.

[Judith]

But then I have people saying, but, you know, it's your mom. She's 72. You might have five to 10 good years with her left and be the bigger person, but when it boils down to it, it's like, I don't want to go to dinner with him because I feel like I can't control my face.

[Boom Boom Hiller]

Well, you've made the choice then.

[Judith]

I think, like, I don't know how to look at him and be kind or nice. I don't trust myself.

[Katherine]

Great. These are all your answers?

[Chelsea Handler]

Answers?

[Judith]

Yeah. I'm not a people pleaser anymore. I don't have to do this. I've learned that lesson. I've pushed through in my 40s to, like, stand up for what I think is healthy and the people I want in my life. But there is some lingering guilt, and I just don't know if I'm being too stubborn, because, like I said, my other siblings have stepped in and tried, and they all say, like, girl, we didn't enjoy it either. But it's one of those things we're doing it for our mom. And I just, just would prefer not to. I just don't know if I'm being stubborn or not.

[Katherine]

I don't think, I don't think it matters that you're being stubborn. I really don't. I think I, I completely support your decision to say where are you in the birth order?

[Boom Boom Hiller]

This is just a kid.

[Judith]

I'm the third of four and we were all, we're all very close. Like my mom had four kids in six years. Wrap your head around that. So it's like boom, boom, boom, boom, boom with us. And we all feel the same way for the first time ever about something. But usually I'm. I'm the people pleasing middle child that can be friendly and like keep her chin up and do whatever. But when I got divorced like eight years ago, I quit doing that. I just don't do that anymore. I'm not performing for anyone. I don't want to have to be forced into things I don't want to be into. And I want to stand in my own power and my own decision making and let the people that I trust into my circle and into my world. And so I did talk to my therapist about just going to dinner with him. And even then it feels like I'm going to be fake or performing for them. And I don't want to put myself in a situation where I'm not being real. You know what I mean? Or authentic.

[Boom Boom Hiller]

You've done the work too. You've like really thought about this and talked about it with your therapist and your siblings. I feel like you've. Yeah.

[Katherine]

I mean, how many more opinions do you need?

[Judith]

Just yours, Chelsea. I just want yours.

[Boom Boom Hiller]

That's nice.

[Judith]

Do you blame me?

[Katherine]

I would trust it, but yeah, for sure. You got it. You got this. Don't do it. Don't do it. Be nice to your mother. Tell her you love her and that you're always open to seeing her. She's your mother. You'll always love her. Reiterate that. Always say that. Make sure she knows. But you're not interested in hanging out with Logan or Larry or whatever the fuck his name is.

[Boom Boom Hiller]

The fact that they met at her funeral, that is.

[Katherine]

No, but this happens on date. I have a grandfather. Not my grandfather, but my nieces have a grandfather. He married his cousin right after his wife died. Like the cousin that looks the most like his ex wife or his dead wife. This happens all over. This happens to men all the time. They. Men can't be alone. There are so and so they Immediately they're like, oh, are. You're alive. Okay, you come with me. It's like, what. What is the. Are there any prerequisites to us being in a relationship? Yeah, literally. I support you. I'm with you.

[Judith]

Thank you, Chelsea. I feel so good.

[Katherine]

But what's up with that dog in the background? Is that dog a Republican? Why, is it not?

[Judith]

No, this dog isn't. That's Texas. Trust me, I'm not a Republican dog.

[Katherine]

Okay, I just want to mention, I fucking hate Republican dogs.

[Boom Boom Hiller]

Do you live in Texas?

[Judith]

I do. I'm in Dallas, but I'm in a very blue, beautiful space. Don't worry. Like, I'm.

[Boom Boom Hiller]

Yeah, the dog is very cute.

[Chelsea Handler]

Thank you, Judith. Will you take a picture of that and text it to me so we can include it in the video?

[Judith]

Absolutely. Absolutely. Yes. I work with rescue animals, and so I'm in my office and we're celebrating big dog energy.

[Katherine]

Oh, good. Okay. Well, thanks for calling in, Judah. Thank you.

[Judith]

Thank you all so much.

[Katherine]

Tell your mom I said hello, girl.

[Judith]

I just hope she doesn't know this podcast happens, so we'll see what happens. Just pray for me on that.

[Katherine]

I doubt Larry's an avid listener, and apparently he's deciding what she's listening to these days. Okay. Okay. Take care, Judith. All right, thank you. Bye. Bye, bye. Don't you feel like we solved the world's problems today? I mean, honestly. Wow.

[Boom Boom Hiller]

Definitely, Judith. Maybe not so much, but.

[Katherine]

Yeah, well, we started with him. I mean, he's got a lot of problems. You know, imagine. Imagine going to a city, moving with somebody on their visa, and then you're beholden to them and you're not really in. You're not sexually attracted. That he has a lot of problems, and if we could solve that in a podcast, then this would be more successful. You know what I mean? We would be getting awards. Michelin star rating.

[Boom Boom Hiller]

Michelin star. We're the first Michelin starred podcast.

[Katherine]

We'd have a bakery. We'd have Michelin stars.

[Boom Boom Hiller]

You guys, just real good questions.

[Katherine]

If we could solve every fucking problem. Problem not solved for Tim. Was that his name? Timothy?

[Chelsea Handler]

Yeah.

[Katherine]

Okay, well, Timothy from South Africa, who's in the Netherlands. Sounds like. I was like, looks like he's searching for Dutch people. Well, we have to wrap things up. This is. It's over. This podcast episode is over. I want everyone. I want every. You've been boom, boomed. I want everyone to order a copy of Actress of a certain age. My 20 year trail to overnight success. It's really worth it. And you've been a pleasure. I'm so happy that. Have we ever met before? No.

[Boom Boom Hiller]

No. But I will. You did one time on Chelsea Lately I did this truly ridiculous musical in real life and you did your monologue about it and you called it a gay hate crime in reverse. And I do have a slight sense of pride about that.

[Katherine]

Okay, well, now I do too. It's wonderful. Wonderful to relive memories like that. To cruise down memory lane. Before our podcast was a Michelin star. Oh, God, what a day. What an afternoon. Thank you, Jeff.

[Boom Boom Hiller]

Thank you. Seriously, thank you.

[Katherine]

Okay, my remaining dates for Vegas. There are remaining dates for this year. Summertime is coming and I will be in Vegas at the Cosmo doing my residency on July 5th will be the next date that I'm there. July 5th, August 30th, and then November 1st and 29th. November 1st and November 29th, I will be in Las Vegas at the Cosmo performing inside myself at the Chelsea. It's called Chelsea at the Chelsea for a reason. Okay, thank you.

[Chelsea Handler]

Do you want advice from Chelsea? Write in to dearchelseapodcastmail.com Find full video episodes of Dear Chelsea on YouTube by searching eercelsea. Dear Chelsea is edited and engineered by Brad Dickert Executive producer Kathryn Law. And be sure to check out our merch@chelsea handler.com.

[Katherine]

Listen up. You know what's better than being a jittery mess after your third coffee? Actually functioning like a normal human being. Beyond Brew by Live Conscious is a six in one mushroom blend that won't make you trip balls, but it will give you mental clarity, focus and less blood. Forbes called Beyond Brew a deliciously potent coffee alternative and 400,000 people can't be wrong. It comes in cacao, caramel macchiato and vanilla latte. Because we are not savages. Your mind and body will thank you later. Go to liveconscious.com and use code Chelsea for 15% off.

[Ryan Seacrest]

Who needs headphones when you have glasses? Ray Ban Meta Glasses with discreet open air speakers and built in microphones, you can play your favorite tunes.

[Katherine]

Hey Meta.

[Ryan Seacrest]

Play hip hop music while staying in tune with the world around you. Ray Ban Meta Glasses choose from a variety of classic Ray Ban frames, all with meta [e-mail] AI classes and don't forget to say hey meta play iheartradio to enjoy your favorite radio stations, artists and podcasts on the iHeart app.

[Jeff Hiller]

Hey, it's Ryan Seacrest for Albertsons and safeway now through July 15th. Stock up on all your favorite personal care brands and earn four times points to use on later purchases for discounts on groceries or or gas. Shop in store or online for items like Pantene Shampoo, Old Spice Total Body Deodorant, Tampax Pearl Venus Razors, Head and Shoulder Shampoo, Olay Body Wash and Pantene conditioner and earn four times points. Hurry before these deals are gone. Offer ends July 15th. Restrictions apply. Offers may vary. Visit albertsons or safeway.com for more details.

[Chelsea Handler]

Every business has an ambition. PayPal Open is the platform designed to help you grow into yours with business loans so you can expand expand and access to hundreds of millions of PayPal customers worldwide. And your customers can pay all the ways they want with PayPal, Venmo pay later and all major cards so you can focus on scaling up when it's time to get growing. There's one platform for all business PayPal open grow today at paypalopen.com loans subject to approval in available locations. This is an iHeart podcast.