Presenting: Dear Chelsea with guest Josh Radnor

Summary

"How We Made Your Mother" Presents: Dear Chelsea with Guest Josh Radnor

Released March 26, 2026
Host: Chelsea Handler (plus Brad Dickers & Kathryn Law)
Guest: Josh Radnor (Ted Mosby in HIMYM; Co-host of How We Made Your Mother podcast)

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Episode Overview

In this crossover episode, Josh Radnor joins Chelsea Handler’s “Dear Chelsea” podcast to discuss his career, personal evolution, creative ventures, and to give candid advice to callers on relationships and personal change. Combining their characteristic humor and frankness, Chelsea and Josh reflect on the enduring legacy of How I Met Your Mother, their own artistic journeys, fame, sobriety, marriage, and the intricacies of human connection—all while answering listener dilemmas with warmth and wit.

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Key Discussion Points & Insights

1. Rekindling Old Connections & Their Shared History

[04:02 - 05:14]

• Chelsea recounts trying to remember how she and Josh know each other; Josh confirms they made out 20 years ago but didn’t sleep together, amusing Chelsea.
• They reminisce about meeting through mutual friends at the Improv, with Chelsea’s bold humor (“You look like a terrorist”) and a later makeout at Josh’s apartment.
  • Notable Quote:

    "We didn’t sleep together, but we made out. I’m happy to talk about it on the podcast if you want."
    — Josh Radnor [04:02]

2. Josh’s Artistic Multihyphenate Life

[05:15 - 08:13]

• Josh explains his dual careers as an actor and musician; shares his journey into music, notably his new album “Eulogy, Volume Two.”

• Reflects on the contrasting cultures of musicians and actors:

  • Music communities in LA and Nashville are “incredibly generous, cool, collaborative.”
  • Acting feels “a little more mercenary,” but music delights him with its newness.

• Chelsea notes this artistic expansion is common among actors but challenging due to public expectations.

  • Notable Quote:

    "Acting is maybe a little more, like, mercenary ... I've been doing it for so long, so I'm a little more delighted by the newness of the music."
    — Josh Radnor [05:59]

3. Artistic Process, Cross-Pollination & Inspiration

[08:13 - 08:58]

• Josh on why some ideas are for film, some for songs: "Different ideas need a different form."
• Chelsea mistakenly credits him for writing Fleishman is in Trouble; Josh corrects her and jokes about starting rumors.

4. Personal Life: Marriage, Children, Sobriety

[09:15 - 10:48]

• Josh is married, has a dog named Nelson, and is “California sober”—uses weed and psychedelics, avoids alcohol.
• Explains alcohol had no “off switch” for him; preference for conscious, healthier altering substances.
  • Notable Quote:

    "I like weed. I like psychedelics. I don't drink. I haven't had a drink in about seven or eight years ... but I still like altering the consciousness. I just don't do it with booze anymore."
    — Josh Radnor [09:52]

5. How We Made Your Mother Podcast & HIMYM Legacy

[11:02 - 15:17]

• How We Made Your Mother podcast concept:

  • Co-hosted by HIMYM co-creator Craig Thomas, inspired by Josh's wife never having seen the show.
  • Less about episode minutiae, more about thematic and cultural impact, what holds up, what doesn’t.

• Josh was the very first person cast in HIMYM.

• Nine seasons of HIMYM = formative chunk of life: “High school plus college plus one year plus like a mini PhD.”

• Discusses the expectations/duration dynamic in show business versus typical employment.

• Describes the unique relationship fans have with "Ted Mosby"—challenges of being closely identified with a fictional role, managing fame and loss of anonymity.

  • Notable Quote:

    "I filmed this thing. I banked it. I've moved on with my life … When they meet me, it's almost like I offend them by having another life and another name."
    — Josh Radnor [15:17]

6. Fame, Typecasting & Self-Reflection

[14:21 - 17:31]

• The lasting shadow of playing Ted Mosby:
  • Struggled not with separating from the role, but with others not willing to see him differently.
  • Rewatching the series now brings him more “compassion” and understanding: the show genuinely resonates with viewers navigating their 20s/30s.

7. Therapy, Growth, and Creative Motivation

[17:42 - 18:58]

• Josh affirms he’s done a lot of therapy.
• Creative drive: each accomplishment opens new doors. Songwriting became a serious craft, apprenticed under Ben Lee.

8. Finding Happiness in the Everyday

[19:04 - 19:46]

• Josh's happiest version of himself: productive creative days, simple pleasures like walking his dog or waiting for dinner with his wife.

• His wife, a psychologist, is a key source of creative feedback and partnership.

9. Relationship Dynamics & Psychological Insights

[19:55 - 22:08]

• Discusses how his wife's “storyteller's instincts” benefit him.
• Chelsea introduces “proleptic irony” (viewer knows outcome before characters).
• Marriage dynamic: balance, respecting boundaries (e.g., journals strictly off limits), supporting each other’s work and psychological load.

10. New York vs. LA Life

[21:48 - 24:19]

• Josh and Chelsea swap observations on how each city impacts their daily rhythms, social lives, and even eating habits.

• Josh relishes New York for its energy; Chelsea jokes that LA is “sleepyville” and is plotting her escape.

  • Notable Quote:

    "LA makes you very elderly very quickly. You're like 5:30 dinner, you're asleep at 8."
    — Josh Radnor [23:49]

11. Listener Advice Segment

[26:52 - 48:48]
Chelsea, Josh, and the team take live listener calls/emails on relationships, change, and self-worth:

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Caller 1: Nikki – Marriage Trust Issues

[27:03 - 33:14]

• Situation: Husband sent flirty late-night texts to another woman; Nikki’s trust is shaken, especially after uprooting her life for his career.
• Advice From Chelsea: Immediate couples therapy; this is a big red flag—“The first time has to become the last time.”
• Advice From Josh: Honesty and transparency must be central; live your life such that “no one needs to go through your phone.”
• All agree Nikki is not overreacting; first year of marriage is uniquely hard—therapy (both couples and individual) recommended.
  • Notable Quote (Josh):

    “Live your life in such a way that no one needs to go through your phone... Your public face and your private face should be the same, especially in your marriage.” [30:10]

Caller 2: Allie – Sibling Boundaries & Identity

[35:33 - 41:26]

• Situation: Close with her brother; struggling emotionally as he gets serious with a new girlfriend; wants to foster independence without damaging their relationship.
• Chelsea: Normalize difficulty with change, especially in very close sibling bonds. Encourages leaning into other friendships, activities.
• Josh’s Analogy:

  “If we’re a solar system and you’re the sun, your brother was Mercury, but now he’s got to be Venus—one planet away... Dynamics have to change, but the relationship continues.”

• All endorse self-expansion, leading with love, and accepting transitional phases.

Caller 3: Stephanie – Work Crush Dilemma

[41:58 - 49:28]

• Situation: Stephanie has a magnetic, mutual crush on her (single, divorced) boss. Wants to make a move but worried about professional repercussions and possible rejection.
• Chelsea: Encourages boldness—"You almost don't deserve to be in love if you won't risk rejection!"
• Josh: Suggests direct, honest, yet lighthearted disclosure: “I really like the notes and our dynamic... can we maybe work in a little bit of making out and just see what that’s like?”
• Consensus: life’s too short, rejection provides clarity, go for it, and report back!
  • Notable Quote (Josh):

    “Rejection is good information. Cause you can move on with your life. It's win, win.” [48:26]

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Notable Quotes & Moments

• On Creative Life:

  "Just like, a good writing day is, like, truly the most satisfying thing for me. When you catch the wave..."
  — Josh Radnor [19:04]

• On HIMYM’s Enduring Appeal:

  "I have a lot more understanding of why people love the show ... it really teaches people something about those years, like those 25 to 35, which are really pivotal, interesting times in people's lives, you know?"
  — Josh Radnor [17:31]

• On Relationship Advice:

  “Rejection is good information. Cause you can move on with your life. It’s win, win—the rejection.”
  — Josh Radnor [48:26]

• On Boundaries:

  “Be kind. Don’t read my journals.”
  — Josh Radnor (on marriage rules) [34:21]

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Important Timestamps

• Josh & Chelsea reminisce: [04:02]
• Discussion of acting vs. music: [05:41]
• Josh's approach to different art forms: [08:13]
• Talking about podcast with Craig Thomas: [11:02]
• Struggles with fame & being Ted Mosby: [14:21]
• Listener Nikki’s marriage dilemma: [27:03]
• Listener Allie’s sibling boundary issue: [35:33]
• Listener Stephanie’s work crush: [41:58]

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Episode Tone & Language

This episode is playful, honest, and refreshingly candid. Chelsea’s quick wit and frank advice set a welcoming, irreverent tone while Josh balances humor with introspective depth. The banter is warm, at-times self-mocking, but rooted in genuine care—whether talking about creative risk, personal growth, or fielding real-life relationship woes.

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Summary Takeaway

This episode is a delightful, vulnerable, and deeply human conversation led by two seasoned storytellers. Through laughter, confession, and practical advice, Chelsea Handler and Josh Radnor model the power of self-knowledge, creative exploration, and leaning into life’s unpredictable changes. Whether reflecting on HIMYM’s pop culture legacy or helping listeners find courage in love and transformation, their insights are equal parts relatable and reassuring.

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Josh Radnor’s new album “Eulogy Volume Two” is available wherever you get your music.
“How We Made Your Mother” podcast now streaming.
Chelsea Handler’s “High and Mighty” comedy tour dates: chelseahandler.com

Transcript

[Josh Radnor]

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[Brad Dickers]

You said you were over him, but his hoodie's still in your rotation.

[Chelsea Handler]

It's time.

[Brad Dickers]

Grab your phone, snap a few pics, and sell it on Depop. Listed in minutes with no selling fees. And just like that, a guy 500 miles away just paid full price for your closure. And right on cue.

[Chelsea Handler]

Hey, still got my hoodie?

[Brad Dickers]

Nope. But I've got tonight's dinner paid for. Start selling on Depop, where taste recognizes taste list. Now with no selling fees, payment processing fees and boosting fees still apply. See website for details.

[Josh Radnor]

Hey, it's Josh. We're excited to bring you something a little different today. I recently sat down with Chelsea Handler on her podcast, Dear Chelsea. It was so much fun. We talked about how we met, how we made out 20 years ago. Sobriety, navigating fame, marriage, my love for New York City. And we got to give some advice to Chelsea's listeners. We're dropping my conversation with Chelsea into the feed here for you today. This is a great podcast. Every week, Chelsea, along with her co host Katherine Law and some pretty great guests, takes on listener questions with that hilarious, unfiltered edge she's known for. One minute you'll be laughing about sex and weed, and the next you're having a deeply moving conversation about grief or family. It's. It manages to be inspirational and heartbreaking all at once. You can check out Dear Chelsea wherever you get your podcasts. And while you're at it, Chelsea is actually on tour right now, bringing that same energy to the stage. Head over to chelseahandler.com to grab your tickets. Now here's my conversation with Chelsea.

[Chelsea Handler]

Hi, Katherine.

[Brad Dickers]

Hi, Chelsea.

[Chelsea Handler]

Hi. I'm in recovery mode.

[Brad Dickers]

Oh, did you. You didn't have a spill, did you?

[Chelsea Handler]

Oh, no, no, no. Not that kind of recovery. I had a lot of people at my last week, and they. And a lot of action, a lot of people, a lot of things. And I am really. I just slept probably 16 hours on Monday and another 12 hours yesterday, so I'm starting to feel back to myself. I have Vegas this weekend.

[Brad Dickers]

Oh, good. You gotta prepare.

[Chelsea Handler]

Yes, I have some new Material that I have to test out for my new tour, the High and Mighty Tour, which starts on February 13, which we've actually made some additions to. We've added some shows. We added Los Angeles. I will be performing at the Netflix is a Joke festival that's on May 6th. We added Rohnert Park, California. The presale is live now, April 3rd, I'll be in Rohnert Park. And also we added Atlantic City, which is on Valentine's Day, February 14th. So those new shows have just been added to my High and Mighty tour. And my first two shows out of the gate will be in Washington, D.C. atlantic City and then Norfolk, Virginia, February 13th, 14th, 15th. I will see you there.

[Brad Dickers]

Excellent. Well, I'm excited about our guest today.

[Chelsea Handler]

Yes. Our guest today has a new album called Eulogy, Volume Two, and he is the host of the podcast How We Made youe Mother. So please welcome Josh Radner. Hi, Josh Radner.

[Josh Radnor]

Hi, Chelsea. How are you?

[Chelsea Handler]

I'm good. How are you doing? You look so professorial with all of those books. I like the. Like the salt and pepper hair and then the books behind you. It's painting quite a picture.

[Josh Radnor]

You got just the vibe I'm going for.

[Chelsea Handler]

You know what I was thinking on my way over to record this podcast today? I was thinking, oh, I'm interviewing Josh Radner. And then I was like, how do I know Josh? And then I was like, did Josh and I ever sleep together?

[Josh Radnor]

We didn't sleep together, but we made out. I'm happy to talk about it on the podcast if you want.

[Chelsea Handler]

Great. Well, we're recording, so let's get started.

[Josh Radnor]

Okay.

[Brad Dickers]

Yeah.

[Josh Radnor]

You know how we met is Matt Boren and Jessica Golden, I think.

[Chelsea Handler]

Oh, Jessica Golden. I remember Jessica. Do you know where she is today? Jessica Golden.

[Josh Radnor]

She wrote me a couple months ago, but remind me.

[Chelsea Handler]

No, I don't know. I'm curious. I haven't seen her in.

[Josh Radnor]

I haven't either. I'll have to check my texts, but they took me to an evening that you were emceeing somewhere. Melrose. What's the comedy club there?

[Chelsea Handler]

Improv.

[Josh Radnor]

Yeah, the improv, maybe. And I think it was my first season hiatus of how I met your mother, and I had a big, long hiatus. Beard.

[Chelsea Handler]

Oh, yes. It's coming back to me now.

[Josh Radnor]

You came up to the bar, and I said, great job. And your first words to me, you said, you look like a terrorist. And then you walked away. But then later that night, we ended up making out.

[Chelsea Handler]

Oh, I knew something happened. I'm so glad My memory isn't just shot. You know what I mean?

[Josh Radnor]

Yeah, but it was 20 years ago, and we didn't sleep together. I do remember that.

[Chelsea Handler]

Okay, great. Well, that's great information to have. I'm glad. And did we make out at the Improv or did we stay out?

[Josh Radnor]

No, no, no. You came to my little apartment for a little while, and then.

[Chelsea Handler]

Didn't you have a roommate?

[Josh Radnor]

No.

[Chelsea Handler]

Oh, I'm okay that I might be confusing you with someone else now. Anyway, it's great to see you again. I've seen you in ages. And you're. Now you're married. Well, first of all, you're Marri, a musician and an actor. I mean, forgive me for not knowing this, but I didn't even know you were a musician. Now, this is great information to have and to spread the word, he has a new album called Eulogy, Volume Two. So there's a Eulogy Volume One, I'm assuming, which I'm gonna listen to as soon as possible, correct?

[Josh Radnor]

Yeah.

[Chelsea Handler]

Okay, here's a serious question. Who is the more annoying group of artists as a successful actor and musician? Now that I know you're both, who is more annoying as a group of artists, musicians, or actors?

[Josh Radnor]

I don't know. I don't think of. I don't classify people by their level of annoyance. But I will say that the musicians I've met, especially in Los Angeles, where I now live in Brooklyn, but the musicians I met in LA and in Nashville, where I've spent a lot of time, have been incredibly generous, cool, collaborative people. Acting is maybe a little more, like, mercenary, like, kind of. I don't know. But I've been doing it longer, the acting, so I'm a little more, like, delighted by the newness of the music. Do you know what I'm saying?

[Chelsea Handler]

Absolutely understand what you're saying. And I have to say, I have a couple of friends who are not. They're not out as musicians yet. They're working on music, but they are actors. Two of them, specifically, that I'm thinking of. And they have the same exact sentiment. They're gonna be coming out with music, and they're both pretty big stars. So, like. And I had no idea. I was like, wait, what? You guys ended without sw because we have to get it right, you know, because we're so, you know, well known in these other arenas. I would imagine the pressure is intense to get it right. But they said the same thing about Nashville, and they also, surprisingly, told me that the music scene in Los Angeles is far more not Adaptable, like, it's just. There's just more going on musically in LA than New York, which surprised me. Would you agree with that?

[Josh Radnor]

That is true. I have found New York. I think it's a matter of like, the venues are just a little more like active in la. So, like, I started playing music at the hotel cafe, which is like an incredibly intimate. You know, there's two stages. The people were so nice. I kept getting invited to these like songwriter evenings and I'd get up and do two or three songs and meet people who ended up becoming collaborators. It was great.

[Chelsea Handler]

Yeah, that is fun.

[Brad Dickers]

It's.

[Chelsea Handler]

First of all, it's so nice to not to have to do one thing. Not that you have to do acting, but you know what I mean? It's what you were saying earlier. I feel very aligned with that. I like to get to do a lot of different things because otherwise I'll get too bored. And what I've noticed, I mean, it could be ADD or however you wanna frame it, or it could just be like artistic behavior, you know, like the life of an artist is like you kind of have to spread yourself around a little. It's not always one thing, I guess, unless you're Van Gogh. It was one thing. But I'm sure he had other tricks up his sleeve too, that we probably don't know about. But I would say that. And then the artistry kind of bleeds into each other. Would you say that that's for me?

[Josh Radnor]

For me, it's kind of like I think about. There's just like different ideas, need a different form. Like sometimes I have an idea and I'm like, well, that's a 90 minute story. Like that's a movie. I have another idea. And I'm like, that's a four minute song. I'm not going to get anything more. It's actually better as a song than it would be in a larger kind of, you know what I'm saying? Like a different arena.

[Chelsea Handler]

Well, you've written and you've written movies too. And you wrote the Fleischman's. Fleischman is in Trouble on Show.

[Josh Radnor]

No, I didn't write that. Taffy Brodisarachner wrote it. I acted in that.

[Chelsea Handler]

Oh, you acted in that. Sorry, I thought you'd created that.

[Josh Radnor]

That's very nice of you to think that. I'll tell Taffy you thought that.

[Chelsea Handler]

Yeah, let's just keep pretending.

[Josh Radnor]

Let's start that rumor.

[Chelsea Handler]

I mentioned Jaws. He also wrote and directed Jaws.

[Josh Radnor]

I did write Jaws. I didn't direct Jaws. I Directed Close Encounters.

[Chelsea Handler]

Can you imagine? I was just. I grew up on Martha's Vineyard, like in the summertime. So they actually shot that movie when my brothers and sisters were in there. Like, you know, kids under 10 years old. So they watched that shark Bruce go up and down in the water in the bay on Katema Bay. And they would not go in the water for 10 years after that.

[Josh Radnor]

Yeah.

[Chelsea Handler]

So what's your story, Josh? You're married. Do you have children now?

[Josh Radnor]

No. We have a dog named Nelson who's somewhere around here.

[Chelsea Handler]

That's a good dog's name and I approve of that.

[Josh Radnor]

Yeah.

[Chelsea Handler]

And are you planning on having children? Are you anti children? What's your stance on Josh?

[Josh Radnor]

I'm not anti.

[Chelsea Handler]

Are you open minded about it?

[Josh Radnor]

Yeah.

[Chelsea Handler]

You are?

[Josh Radnor]

Yeah.

[Chelsea Handler]

Okay, good to know. Great. Just getting to re know you.

[Josh Radnor]

Yeah. We didn't cover everything the night we met.

[Chelsea Handler]

We don't. I do. I mean, yes. How could we have? We were obviously we were busy. Yeah, we were busy. I was sure I was. Had a serious buzz going. Are you sober now?

[Josh Radnor]

I'm like California sober.

[Chelsea Handler]

Meaning only weed. Is that right?

[Josh Radnor]

I like weed. I like psychedelics. I don't drink. I haven't had a drink in about seven or eight years. But I still like altering the consciousness. I just don't do it with booze anymore, you know?

[Chelsea Handler]

Yeah, that seems to be the trend, you know, I mean I still drink cause I have a real affinity for alcohol. But I definitely drink a lot less because of all of the other good stuff available now. Like the healthier stuff. Like if you're microdosing, whether it's psilocybin or LSD or whatever you're into, you don't. You definitely don't drink as much as I used to for sure.

[Josh Radnor]

Yeah. For me alcohol was just, just unleashed some part of me that was not great. I also, I don't know, I have it in my family. It just felt like a good move to make. But I still like, I didn't have an off switch with alcohol. I have it with everything else.

[Chelsea Handler]

Yeah, that's interesting.

[Josh Radnor]

Yeah.

[Chelsea Handler]

Yeah. There's a lot of people that don't have an off switch with alcohol.

[Josh Radnor]

I was like, if one is good, four is better. Know.

[Chelsea Handler]

Yeah, four is better. And then you get that look in your eye, that empty vacant look in your eye and you're like, ah, it's time to take you home, sweetie. Sometimes you're talking to yourself. You do this podcast, a watch podcast with How I Met yout Mother. You rewatch episodes together and discuss.

[Josh Radnor]

Well, yeah, it's with. It's with the. One of the co creators of the show, Craig Thomas.

[Chelsea Handler]

I already told you, you've created everything that we're going to talk about today.

[Josh Radnor]

Yeah, yeah, I've created.

[Chelsea Handler]

So it's cute if you want to shout out names to other people, but we're just going to edit that from the podcast.

[Josh Radnor]

It's called How We Made youe Mother. It started because my wife Jordana had never seen the show and she really wanted to watch and I kind of felt like ready to watch it again. I hadn't seen it in so many years. So I called Craig, who's a really dear friend, and I love talking to him, and I was like, do you want to do something a little more formal and just like go through the show and talk about it and you know, it's a rewatch and we don't cover it in like granular detail every episode, but we really do talk about, like the major kind of themes of what was up. We talk about what worked still. What didn't work would no longer kind of work. It's kind of like this meta thing because the whole series was structured as this older guy looking back on his younger years, and now we're like, older looking back on this thing we made.

[Chelsea Handler]

I know that show was. That was like nine seasons, correct?

[Josh Radnor]

Yeah.

[Chelsea Handler]

So. And you were the very first person cast in that show. Is that accurate?

[Josh Radnor]

That is true. Yeah. Me and Coby Smulders were the first. Yeah. But I was the very first person who auditioned on the very first day. That is true.

[Chelsea Handler]

That's wild. Okay. Yeah, that is wild. I mean, nine years of your life is such a big chunk of your life.

[Josh Radnor]

So big. Yeah. I always thought about it. I was like, it's high school plus college plus one year plus like a mini PhD. Yeah. A gap year or whatever. I mean, it. It was so long and. And also it flies by. I mean, it's so weird. Like the thing you're describing of, like, wanting to go from thing to thing, that's like a little thing probably we share is like a little bit of a mercurial personality. Like we want to go from thing to thing. And you never think when you get into this industry, I'm going to be doing something for nine years. Like, that's insane.

[Chelsea Handler]

Right, Right. And also in a. In like the regular world, if you were to go into any job, I wonder if people want to go into a job thinking, I want to be here for nine years. You know, usually if you're really kind of like my professional friends go to a company and they'll be like, oh, I'll stay here for five to six years and then I'll move on to something else.

[Josh Radnor]

Right.

[Chelsea Handler]

But I don't know if that's like a different level of employment, you know, or if some people are just looking for any stability whatsoever. But if you were to go into something knowing it would last that long, I wonder if our decisions would be the same.

[Josh Radnor]

Well, you have to. I mean, when you, when you test for the pilot, I think it's still like this. You have to sign a seven year contract, you know, so. But statistically that never happens, you know.

[Chelsea Handler]

Right. But. And in your case, it exceeded the seven years. But you're so grateful in that moment when you're signing that fucking, you're like, please give me seven years of a salary, please. You never could imagine that you would either grow bored. And I'm not saying you did. I just speak from my own experience. That you would grow bored or experience any sort of ennui or, you know, like, get tired of something.

[Josh Radnor]

Well, I was like, please give me my health insurance. Like, I was like, really wanted something to go. And if you look at nine years of your life, any nine year chunk, you're going to be bored, frustrated, elated, like it's everything. You know what I mean? Like, no one wants to hear that you had a bad day on your hit TV show. But, like, of course you do. You know, you also have really fun days.

[Chelsea Handler]

Yeah. And you had such a great cast. I mean, everybody in that cast is a solid, normal, mostly normal person. I don't know them.

[Josh Radnor]

Depends on the day. But yeah, mostly.

[Chelsea Handler]

Yeah. Well, of course, I mean, we are dealing with actors, but as far as actors go, you got a good batch to work with, that's for sure.

[Josh Radnor]

Yeah.

[Chelsea Handler]

I love Cobie Smulders. I love Jason Segel. I love Kaley. Now, it says here that you struggle to separate yourself from the role that you played and that you struggled with fame. Talk to me about that.

[Josh Radnor]

I wouldn't say I struggled with separating myself from the role. I felt like I struggled with other people not willing or wanting to separate me from the role. You know what I mean? I knew who I was all the time. I knew who I, you know, I knew I was playing a role. It's like, you know, it's such a. It's such a head trip. Like so many people and people watch the show over and over. There's these people that are. I love Them, but they're obsessed with the show, and they watch it over and over. So they've spent so much time with me as this one person. I filmed this thing. I banked it. I've moved on with my life, and I've. I don't think about that. I don't know the show the way they know the show. I don't. I'm not saturated in it the way they are. So when they meet me, it's almost like I offend them by having another life and another name and another. You know what I mean?

[Chelsea Handler]

Yeah.

[Brad Dickers]

I will say, of anyone we've ever had on the show, I think you have the most thriving, like, Reddit life. Like, you know what I mean? Like, people are out there, like, still having conversations about the show.

[Josh Radnor]

Oh, yeah, A lot. Yeah. No, it's crazy. It's wild. And I was just on Jesse Tyler Ferguson's podcast, we were just talking about. Because he was on Modern Family for so long, and we were talking about the weirdness of people wanting you to be that character and interpreting everything you say and do through the lens of the character. So it was strange. I mean, I think there was one level. It was that, and the other level was just the erosion of anonymity. And it was weird. I just found it very destabilizing. I'm used to it now. Like, I know how to walk through an airport and take a few photos of people and move on with my day. It's not, like. It's not a huge deal, but, like, at the time, I was really unsettled by it.

[Chelsea Handler]

Yeah, I would imagine that's true for a lot of actors. For me, I'm like, you know, I am kind of what I am on tv. So it's a different. I'm not playing a character.

[Josh Radnor]

Right.

[Chelsea Handler]

You know, my Persona is who I am pretty much. You know, luckily, it's even better. I mean, hopefully it's even better in person, but I don't struggle with that. So I'm always curious to hear actors talk about that, because it would be really fucking annoying for people to expect you to be character in the middle of the day on a street in Los Angeles. That's really annoying.

[Josh Radnor]

Yeah. Yeah. I had a girlfriend years ago who said, man, you're a lot nicer when people come up and say your real name and want to talk about one of the movies you've directed. You know, like, I just had this weird. But I've really. I've made peace so much with it. And part of it, the rewatching of the show has brought me some peace where I'm. I. I remember watching these episodes, you know, 20 years ago, and I was so hard on myself. But now I watch it and I'm like, you were young. You were also doing a really good job in a really hard role. Like, I have a lot more compassion for myself at this age. Looking back on it, I also have a lot more understanding of why people love the show in some weird way. Like, I couldn't understand why people are so obsessed with it. I mean, I was like, it's good, but why have you dedicated your life to it? Like, why is it a religion? But now I get that. Like, it really teaches people something about those years. Like, those 25 to 35, which are really pivotal, interesting times in people's lives, you know?

[Chelsea Handler]

Right. We're talking about the show How I Met yout Mother, and then we're talking about Josh's podcast, which is how we made your mother. It sounds like you've also done a lot of self reflection and, like, probably therapy, I'm assuming. Correct?

[Josh Radnor]

Sure, yeah.

[Chelsea Handler]

From everything I'm, you know, was reading about you in preparation for this interview, it sounds like you have a. A lot of, like, stuff you want to get out. You know, especially with the music, it's nice to have the freedom to be able to direct, to be able to act, to be able to sing. Like these guitar ballads that are on your album that I was reading some of the lyrics of. And it's really just a testament to the creative spirit, I think, when you really could do all of these things aptly and want and have the desire to keep doing it and keep producing things.

[Josh Radnor]

Yeah. Yeah, thanks. I mean, I. You know, when I was in drama school, like, I just wanted to do an episode of Law and Order. And then you do that and you're like, oh, wait, maybe I could actually be on one of these shows for a while. Or maybe I could be on Broadway. And, you know, it's hard because the carrot keeps moving, but at the same time, when you do one thing, it kind of, like uncorks this thing of like, oh, what if I tried that? Or, what if I tried that? And I started writing songs with my friend Ben Lee, who's a great Australian songwriter. So I kind of apprenticed with this great songwriter. Like, I took it very seriously as a craft. You know, I was. I didn't, like, go in with the producer and be like, here's three lines. Make a song. Like, I really tried to get under the hood of how songs are made. And it's just been. It's been so satisfying.

[Chelsea Handler]

Oh, that's so nice to hear. Where do you think you find your, like, happiest version of yourself?

[Josh Radnor]

I feel like when I have my hooks in a song or, like, a script and there's like. Just like, a good writing day is, like, truly the most satisfying thing for me when I'm. When you catch the wave, you know, and it's not like. I mean, I don't mind, like, chiseling away at something, but, like, when you catch a wave, there's kind of a thing of, like, the afternoon walk with my dog and then writing a song. And my wife is a psychologist, like, waiting for her to come down from the office and get dinner in our sweet little neighborhood. Like. Like. Like pleasures are, like, small these days, but. And I mean like, cosmically big, but small in. In the grand scheme of things. And I've really liked the last year and a half we've been married. Has just felt very sweet.

[Chelsea Handler]

That's sweet. I love to hear a straight man talk like this. Now, what is your. So your wife's a psychologist. How does that play out in your marriage?

[Josh Radnor]

It's good, because I'm pretty psychologically minded, you know, and I can speak that language. And she really loves stories and television and movies. And she has no desire to be in front of. But her story instincts are unbelievably good. Like, she always knows what's about to happen in something. She's, like, always a little bit ahead of things. And when she reads things, I really trust her eye and her ear. Like, she's a great shadow collaborator in certain ways.

[Chelsea Handler]

I just read this term called proleptic irony. Do you know what that is?

[Josh Radnor]

No.

[Chelsea Handler]

When the audience knows. It's just what you're describing about your wife. When the audience knows something's gonna happen in a movie or a book before the characters do.

[Josh Radnor]

Oh, yeah.

[Chelsea Handler]

So as the reader or as the viewer, it's called proleptic irony. And then there's another part of. There's another form of irony which is not as relevant to this conversation. But I thought that was such a good thing that there was a term for that.

[Josh Radnor]

I like knowing that. Thanks.

[Chelsea Handler]

Yeah, yeah, yeah, exactly. Does she psychoanalyze you ever? Or is she just too tired from working that.

[Josh Radnor]

She doesn't have time for that legitimately. She is too tired. She doesn't. We don't really do that. I mean, it's more of like. Do you want, like. What was that I heard A great thing that was like, when someone comes to you and they're all worked up, you say, do you want a toolbox, a tissue box, or a soapbox? So it's like, the soapbox is like, you just want to vent. The toolbox is, do you want some help working through this? And the tissue box is like, do you just want to release it and let it go? And I think we're pretty good. Like, I've had enough relationships where I'm like, I don't do the fucking thing. I mean, sometimes you fall into it, but, like, I don't get in there and try to fix it. It, you know? But a lot of times she's so. She's seen, you know, six or seven patients in a day, and she's like. And on Zoom. Right. And she is. That is closed for business. Right. So then we're just figuring out where to go to dinner, you know?

[Chelsea Handler]

Yeah. That's nice. It's nice to figure out where to go to dinner in New York City.

[Josh Radnor]

I love that we're in Fort Greene, which has some of the best restaurants in New York, and we went to Italy on our honeymoon, and we were like, I mean, it's good, but, like, it genuinely. You get spoiled in New York.

[Chelsea Handler]

It's not as good as New York.

[Josh Radnor]

I mean, some of it is. Yeah. You. Sorry. Italy. We had a great time, though.

[Chelsea Handler]

I know. I think you're right, though. Like, it's kind of like Mexico you go to. Like, I was in. Like, I go. When I was in Mexico City, I was so excited about all the food, and I was like, this is not what I envisioned at all. And I'm like, I feel like we might have better Mexican food in Los Angeles.

[Josh Radnor]

Yeah. It's almost like. Do you remember that movie, John Carter? It was basically like a novel that George Lucas plundered for all this inspiration for Star wars. And then they made a John Carter movie, and then everyone's like, it's like a Star wars ripoff. And it's like, no, that was the original thing that George Lucas loved. And I feel like Italian food or Mexican food is probably like that, where it's like, that's the OG Thing. But we, like, took it and made it something else.

[Chelsea Handler]

Yeah, exactly. So now it's like, that's what we've acclimated to. And we're like, we think that's right.

[Josh Radnor]

Exactly.

[Chelsea Handler]

Exactly. Same thing with pizza. You know, there's that famous pizzeria in Rome. Did you go to Rome on your honeymoon?

[Josh Radnor]

No. Well, we Flew through. We were up in the north.

[Chelsea Handler]

It's like called the cemetery or something. It's. Everyone goes here. And I went there and I was like, this is really disappointing. Meanwhile, you know you can't say anything. Cause you're like, fuck. I don't even wanna sound like an idiot, but I do not like this. If I lived in New York, I would just be twice the size of myself. Every night before I go to bed in New York City, I have to have a piece of pizza.

[Josh Radnor]

Yeah.

[Chelsea Handler]

And I hope if I lived there, I wouldn't act like that. Because I do wanna live in New York City one day. I just have to wait for my hell that is Los Angeles house to be done being built. Which I bitch about on this podcast all the time. So there's. You shouldn't be privy to it as well, Josh.

[Josh Radnor]

That's fine. But also in New York, you end up eating at like 10 o'. Clock, like a full dinner at 10 o'.

[Brad Dickers]

Clock.

[Josh Radnor]

And LA, you're just. It's a whole different.

[Chelsea Handler]

I would like to be up at 10 o'. Clock. You know what I mean?

[Josh Radnor]

Yeah.

[Chelsea Handler]

And that New York would even provide me that. LA is sleepyville now.

[Josh Radnor]

LA makes you very elderly very quickly. You're like 5:30 dinner, you're asleep at 8. You know what I mean?

[Chelsea Handler]

Like I said, I have to move to New York soon because otherwise I will be too. Like, at least it's motivating. You're always going out and there's too much happening around to not participate in some of the action in New York. I was just telling my friend, I'm like, I'm gonna have to move to New York, otherwise I'll die in like five or 10 years. Because all I do when I'm in LA is sleep.

[Josh Radnor]

I know.

[Chelsea Handler]

I honestly went to bed last night at like 8:45. I was like. I took it edible and I was like, oh, fuck it.

[Josh Radnor]

Yeah.

[Chelsea Handler]

You know, like, what am I watching? Nothing important right now.

[Josh Radnor]

I just sold my house in la. Like, I'm fully living in New York. I like, I just closed on it like three weeks ago.

[Chelsea Handler]

Could you have sold my house with your house as like a little couplet?

[Josh Radnor]

Where are you staying in the meantime?

[Chelsea Handler]

I'm staying currently with my friend Kat. Thank you, Kat. She's put up with me. We're like basically turning into a lesbian couple. She cooks, she's a busy career woman. She takes such good care of me. I bring nothing to the table in terms of domesticity. I am as useless or as Useful, I should say as an ashtray on a motorcycle when it comes to domesticity. But I provide personality, and I like to finance things, so that's what I'm good for. You know, you have to find your strengths in this world, and those are mine, Josh. Those are mine. On that note, we're gonna take a break, and we'll be right back with Josh Radner. The UPS Store is making packing and shipping Easter gifts quicker than ever this year with UPS Air. How quick? Quicker than a walk around the park. Quicker than eating all the Easter candies. Quicker than finding a golden egg that you know is stuffed with cash. When you ship UPS Air at the UPS Store, your items arrive on time or your money back, guaranteed at no extra cost. Exclusively at the UPS Store US retail locations. Send Easter Joy on time at the UPS Store. Visit the upsstore.com air guarantee for full details. Terms and conditions apply. Have you ever felt like you were living just a B or B plus life? It's so dangerous to live that. More dangerous than a B minus or a C plus life? Because when you're living a B, B or B life, you don't change it. You think it's good enough. Is it? I'm Susie Welch. I host a podcast called Becoming you. People think okay. An A life is not available to me, but there is a way. We are all in the process of becoming ourselves. Listen to Becoming youg wherever you get your podcasts. Springfest means more sun, more fun, and more free at Lowes. Keep your yard in line with an additional free Ego Friend 56 volt battery when you buy a select ego mower trimmer or blower. Plus, keep landscaping fresh with stay green. 1 cubic foot garden soil, 5 bags for $10. Our best lineup is here at Lowe's, valid through 4. A while supplies last selection varies by location.

[Josh Radnor]

Soil offer excludes Alaska and Hawaii.

[Chelsea Handler]

And we're back with Josh Radner. He has a new album out called Eulogy Volume two, and everything's just under your name. You don't have a ban.

[Josh Radnor]

No, just my name. Yeah.

[Chelsea Handler]

Josh, are you ready to take some questions from some callers? We. We dole out advice here like professionals.

[Josh Radnor]

Oh, wow. I didn't know this. Okay, yeah, I'm up for it.

[Chelsea Handler]

You're gonna love it. Everyone loves it.

[Brad Dickers]

Yes. Well, our first question is just an email. This comes from Nikki. She says, dear Chelsea, I'm writing because I'm struggling with a situation in my marriage and could really use some outside perspective.

[Chelsea Handler]

Oh, perfect. We have a married man here right Exactly. And a married woman.

[Brad Dickers]

Yeah, exactly. My husband and I have been married for 10 months. Eight months ago, we moved across the country for his job, which meant I had to leave all my friends and family behind. We're still adjusting to the new city and he now travels frequently for work. A few weeks ago, I went to visit friends and while I was gone, my husband went out to a bar. I had this nagging feeling and knew something was off when I got back, so I ended up going through his phone. I know, I know. Not proud of this. What I found was that he had texted a girl he met at the bar around 2am he had apparently left and he was asking her to come back out to the bar, offering to pay for her Uber. It didn't seem to go beyond texting, but the fact that he was actively pursuing another woman while I was visiting friends, the friends I had to leave behind because of his career, feels like such a betrayal.

[Chelsea Handler]

Totally.

[Brad Dickers]

When I confronted him, he apologized and seemed genuinely sorry. But I can't shake the feeling that he's getting more comfortable seeking attention from other women. The combination of frequent travel, us being apart often, and now this incident has my trust at an all time low. Here's what I'm struggling with. I hate that I felt compelled to go through his phone, but my gut instinct was right now I'm worried he'll just get better at hiding things. I also feel especially vulnerable because I'm isolated in this new city without my support system, and it feels like he took advantage of that the moment I left town. We're planning to have a serious conversation about this and I'm considering couples therapy. But I'm not sure if I'm overreacting or if this is as big of a red flag as it feels. How do I know if this is something we can work through or if I'm just setting myself up to be a detective in my own marriage? And how do I deal with the fact that I moved my entire life for someone who might not be as committed to our marriage as I thought? Thanks, Nikki. That's a lot.

[Chelsea Handler]

Wow. I would say that's a big, big red flag and really unfortunate. First of all, I'm so sorry, Nikki, that you're dealing with that, but I'm of the belief that, like, when something like that happens, it has to become such a big deal to make the first time, the last time. Like you have to get into counseling right away with somebody with a therapist to understand why he would even allow himself to get to that place to Be drunkenly Texting somebody at 2:00 clock in the morning is so disrespectful, so unacceptable. You're 10 months into your marriage. That is a huge red flag that he's doing that.

[Josh Radnor]

Yeah.

[Chelsea Handler]

And while I wouldn't say like, oh God, you gotta divorce him, you have to immediately draw attention to the matter. There have to be consequences to those kinds of actions. I don't care about anyone going through anyone's phone. I mean, it's not ideal, but if somebody does and they find something, it's usually because female instinct. And you want to like, you're not pouring through your husband's phone all day long. But now that she saw that, she's going to do it again.

[Brad Dickers]

It's woman's intuition. Like, we kind of always know. And I do agree with you. I think that this is something that they can work through. But like get into therapy immediately and this is not gonna be two sessions. He's obviously having some Peter Pan stuff about like, oh God, I'm married now, I still wanna sow my wild oats. But like, I do think if he's committed to getting past that, you guys can get past it.

[Chelsea Handler]

Right. What do you think, Josh, from the male perspective?

[Josh Radnor]

Well, I think first of all, it's like a pretty insightful letter. Like she has some real self awareness and I think that that is terrific. I hope her husband has similar kind of self awareness. He might be in a fog of like you said, like Peter Pan. Like, I understand all that. It's like women have their own version of this, but I think men, sometimes marriage can feel like the end of hanging up some aspect of yourself that was like, that's very energizing and fun and exciting. But in a good relationship, all that stuff can come out to play and still be active. But I think you're right. It's like, it's no good. I mean, it's almost like live your life in such a way that no one needs to go through your phone. Like that's a good way to be, you know, like you, you want to feel like your public face and your private face are the same, especially in your marriage. I mean, if I was like keeping massive secrets from my wife, I would find this marriage really hard to be in. So, yes, I feel like you gotta, you gotta establish guidelines where it's like we're transparent with each other, with where the behavior doesn't. You don't have these side behaviors because you're obviously trying to escape something. That's a bigger issue which is why couples therapy is inevitable for these.

[Chelsea Handler]

Right? Couples therapy and then individual therapy for him, too. Because it's also really so unfair to put your partner through that. To know that she has a job that takes her out of town. And now every time she goes out of town, this is what's going to be on her mind. Instead of her being able to focus on her job and being able to, you know, the best person in her career that she can be and all of the goals that she wants to attain or reach or aspire to, whatever. Like you're putting an onus on her now to actually have to be preoccupied with your childish behavior. And because you're drunk at 2 o'

[Josh Radnor]

clock in the morning, her in, like, the mother role and him in the child role, which is very unsexy. I would say that her larger question am I overreacting? I would say no.

[Brad Dickers]

Yes. Correct.

[Chelsea Handler]

Right. We all agree that you're not overreacting.

[Brad Dickers]

And, you know, I think people don't talk enough about how hard that first year of marriage can be. I know in my life, like, we went through probably like two years of therapy. About a year in, we started going to therapy. And, like, I just didn't know what I didn't know. You know, it really helps. It's why I'm still married 20 years later or 15 years later.

[Chelsea Handler]

And what were some of the, like, the challenges of being married in your first year?

[Brad Dickers]

Well, it's a big adjustment. Like, even people. I found friends of mine who are like, well, we've been living together forever, so it's not gonna change any. I think it's an expectation shift where people are like, oh, they're gonna come home at a certain time, or we're gonna, like, you know, no one's gonna stay up watching tv. We're gonna go to bed together, whatever. Like, little.

[Chelsea Handler]

How annoying.

[Brad Dickers]

There's a lot. There's a lot.

[Chelsea Handler]

I mean, having to go to bed together every night, I mean, opt out of that. I think any healthy couple doesn't do that every single night. Obviously you can't. I mean, that's.

[Josh Radnor]

I have some friends who've been married a long time and they maintain that as their secret is they go to bed at the same time that they

[Chelsea Handler]

go to bed together every single night at the same time.

[Josh Radnor]

Yeah.

[Chelsea Handler]

Oh, wow. Wow. Interesting. I'll have to think about that on my drive home. I'm not so sure about that.

[Brad Dickers]

I will also say, I think one of the big keys for us was like, you know, they say never Go to bed angry. For us, it was like, go to bed angry because you. Like, maybe I've had a couple drinks, and even if not, you're tired, you're grumpy, you're circling the same drain over and over and over. Like, go to bed. You wake up and you're like, what were we figuring out?

[Chelsea Handler]

It's like holding off on sending that email at night, you know, an angry email.

[Josh Radnor]

That's the most, like, common, somewhat dumbest marital advice. Everyone says it, and you're like, no, think about that. Go to bed angry sometimes and wake up and be in a better place.

[Chelsea Handler]

Yeah, but also, who fucking came up with that? That we have these. Like, it's one of those axioms of life, like, don't go to bed angry. It's like, almost like something that, you know, any idiot could have said. And then everyone's like, yeah, let's repeat that. Rinse cycle and repeat.

[Brad Dickers]

Yeah.

[Chelsea Handler]

Do you have any rules that you and your wife follow about maintaining? I mean, you obviously seem very well balanced, Josh, in that, you know.

[Josh Radnor]

Well, it's been a hard one. It hasn't always been that way. My wife had. She said, I only have two rules, which I thought were incredibly sensible. One was, be kind, which I think is great. And the other one was. She said, don't read my journals. She's kept journals, like, for years and years and years.

[Chelsea Handler]

And she's.

[Josh Radnor]

You know, and she has a friend that in the event of her untimely death, her one job is to come to the apartment and get all the journals and burn them. Like, she's very sincere about. Like, no one is to see these. These are just for me, which only

[Chelsea Handler]

would pique my interest more.

[Josh Radnor]

Yeah, no, it hasn't. I honor it, but.

[Chelsea Handler]

Yeah. I mean, that is such a. Talk about a betrayal, reading somebody's journals.

[Josh Radnor]

My terrible, terrible.

[Chelsea Handler]

I can't even believe people still write with their hands. I had this. I had this. I got that new gratitude journal, and I was like, okay, I want to do it in the morning and at night, every night. And then my friend's like, oh, you could do it on your. You know, you could download the app and do it on your phone. I'm like, I could type. I'm like, I could only get through. You know, when you're writing now, it's, like, so hard to write for some reason.

[Josh Radnor]

Like, I don't know. What are you doing?

[Chelsea Handler]

I know. And I can't fit all the words. It's like, my handwriting sucks now, and I'm like, if I type it, I get so much more in. Then I want to list 10 things instead of three things, you know, that made today great, et cetera. So, yeah, I'm all about the phones now. I've given up. Up. We're living through the technology age, and now we're living through the artificial insemination and intelligence age. Two things I don't want anything to do with. I don't want to deal with AI.

[Brad Dickers]

Well, our next email comes from Allie. She is calling in, so she says, my Name's Allie. I'm 32, and my brother, 31, is my best friend. Don't worry, I have other friends. Like a healthy number, but for a lot of reasons, including complex family dynamics, our shared dark sense of humor, and the bond we formed caring for our grandma during her dementia years. He's been the most important relationship in my life for a long time. Here's where it gets tricky. In the past year, he's entered a serious relationship. I've known this girlfriend for years, and I think she's lovely. This isn't one of those I hate my brother's girlfriend situations.

[Chelsea Handler]

Sounds like it's going to be, though.

[Brad Dickers]

But something about it just isn't fully clicking for me emotionally. It's not jealousy and it's not drama. It's just change. And apparently I'm not thriving in it. We live next door to each other because of course we do. And I'm realizing I've built a little too much of my identity around this brother bestie dynamic. Most of my other close friends are getting married, having babies, or moving on to new life phases. And while I'm good with my own path, I think I need more tools to invest in me again. So how do I begin to lovingly create space between me and my brother, who is, again, still my favorite person, without feeling like I'm pushing him away. I don't want to be weird or dramatic. I just want some practical, emotionally intelligent action items for carving out a little independence without breaking the bond.

[Caller]

Allie.

[Chelsea Handler]

Hi. Ali, this is our special guest today, Josh Radner. Hi.

[Josh Radnor]

Hi.

[Chelsea Handler]

Nice to meet you. That's so sweet that you're best friends with your brother. I love that. That's really nice. I understand that you're dealing with change, but you know what? Listen, this is not like everyone has problems with change. I mean, not everybody, but so many people have problems with change and have problems with making adjustments and actually, you know, having somebody else come in. Even if your best friend wasn't your brother, it would probably Be hard for you for your best friend to have a relationship and being introduced to them. So give yourself a little bit of grace. And I would just whatever you're into, just, like, exercise more of those activities. Like, literally, like, if you're in a Pilates, make sure that you're allotting time for that. Make sure you're allotting time for your friends. You have friends, I'm assuming?

[Caller]

I have a lot of friends. I go to Pilates every day.

[Chelsea Handler]

Perfect.

[Caller]

I do pottery.

[Josh Radnor]

You intuited that, Chelsea. Amazing.

[Chelsea Handler]

And you have hobbies. You like pottery?

[Caller]

It's more like. Like I said, I, like, love his girlfriend. I think she's fantastic. I just realized, like, when he got into the relationship that my identity was, like, more closely tied. And, like, right now, it's fantastic and amazing. Everybody's out here. There's, like, a lot going on, but in the off season, there's not a lot going on. You know, it's like small town, you know, everyone. It's very condensed and, like, everyone's in each other's business.

[Chelsea Handler]

And do you feel like during those winter months when it is quieter, that you are encroaching on their private life? Like, because I don't think your identity is tied to your brother. Unless you actively like your brother and sister, that's not gonna change.

[Caller]

Yeah, we're very much in, like, the same, like, social circle, too. And I just, like, I felt like,

[Chelsea Handler]

oh, my God, like, I don't need

[Caller]

to be, like, third wheeling with his

[Chelsea Handler]

girlfriend all the time. Like, it was just like, I. I

[Caller]

just want to be, like, like, chill and cool and like, I don't know. I don't know. It's a. It's like, I don't. I don't know if there's, like, a correct answer or, like, even, like, a piece of advice.

[Josh Radnor]

Can. Can I offer something, Ally? Perhaps, like, my wife has this theory that, like, if we're a solar system, like, and you're the sun, your brother was like Mercury, but he might have to be Venus. Like, he might have to, like, go, like, one planet away.

[Chelsea Handler]

Ooh.

[Josh Radnor]

You know, where it's like, you're still in relationship. You're still in the same solar system. And I think when people partner off, dynamics have to change because the primary relationship is, like, the relationship.

[Chelsea Handler]

Yeah.

[Josh Radnor]

You know, Totally.

[Caller]

I love that analogy.

[Josh Radnor]

Isn't that cool? I think there's, like, a really cool opportunity for you to, like, what Chelsea said, like, lean into other stuff, grow other parts of yourself, also grow other friendships. And you Know, just follow the seeds. And then I think your relationship with your brother will, like, take its new place in the solar system and it'll start to feel right. But you're just in the, like, adjustment change period, which is.

[Caller]

Yeah, it's like a meteor, like, around.

[Chelsea Handler]

Yeah, you're, like, in the liminal phase. That's what that is. Right. Where you're kind of in between two things, but also just, you know, like, in thinking about it, in thoughts, like, towards your brother, towards his girlfriend. How long have they been together?

[Caller]

Like, over a year.

[Chelsea Handler]

Okay. Just, I would say, like, lead with your heart and lead with love. Like, don't overthink things too much. Don't think, oh, my God, am I spending too much time here? Like, you can have those thoughts, but don't overanalyze your relationship because it is your brother. You do have a relationship. It sounds like you have a pretty healthy relationship with his girlfriend. You know that you're gonna, like, try and grow these other parts, as Josh said, very eloquently grow these other parts of yourself, but also just lead with love. Like, don't punish anyone for these circumstances and don't make it, like, you know, oh, I'm not gonna be available to them because I don't want them to think I'm too available. Like, I have my own life. Like, don't play games like that. Just lead with your heart and really be. Try and be as present as possible when you're with both of them. Because. Because, like, what Josh said, I wanna echo. Like, there is a new version of this coming around, and it's in these in between stages that get so sticky, I think, for all of us when we don't know where what, you know, what we knew is not exactly right anymore and what's to come isn't exactly happening yet, so we kind of get stuck. And it's actually a really nice phase for you to really get in touch with yourself and really be present in the relationship and show up, like, heart forward, love first and totally with no judgment towards yourself or them. Them.

[Caller]

Yeah.

[Chelsea Handler]

Okay. To practice that. Yeah.

[Caller]

Okay.

[Chelsea Handler]

Well, thanks for calling in. I love that question and I love Josh's answer. And I feel like. Yeah, good. Good. Good luck with everything.

[Caller]

Thank you. And good luck with whatever you're promoting.

[Brad Dickers]

Josh can't wait to listen to the

[Chelsea Handler]

episode and hear he's got a new album out. He's got a new album out. You can download yes.

[Caller]

Oh, Fun. On Spotify right now or download on itunes.

[Chelsea Handler]

What's whatever Eulogy Volume 2 by Josh Radner. You could download it anywhere. Yeah, okay.

[Brad Dickers]

Amazing.

[Chelsea Handler]

Well, thank you. Awesome.

[Brad Dickers]

Thanks, Allie.

[Chelsea Handler]

Your new album is gonna get her into her Venus dynamic with her brother. She's gonna end up sleeping with her brother. Watch what this podcast leads to.

[Brad Dickers]

Uh, oh, well, our last question today comes from Stephanie, and she is 48. She says, Dear Chelsea, I recently started working for a small, ish local business. My friend connected me with the owner and we instantly had a connection, even before we met in person. Once we met in person, it was even more intoxicating. Nothing inappropriate has happened, but over the last five months, I have just crushed so hard. It goes in waves where he, I think, flirts with me and then stops. We really get along and just mesh. I think constantly that I just want to make out with him. It's to the point where we're passing friendly work, appropriate touches. We text each other randomly almost just to let the other know the other one know we're thinking about each other without actually saying it. I've never in my life been this drawn to someone so magnetically. He even gave me a plant. If that wasn't a sign, I don't know what is. I mean, a love fern. Who does that? I don't want to get fired. I don't think he would, but I also don't want to quit because I love my job. How can I just make out with him?

[Chelsea Handler]

Just do it already. What? Hello. Hi, Stephanie. This is our special guest today, Josh Radner. Say hello to him.

[Josh Radnor]

Hi.

[Chelsea Handler]

Hi.

[Caller]

Hi, Josh.

[Josh Radnor]

Hi.

[Chelsea Handler]

Look, you look like you're, like, having an affair sitting there like you act like you're doing something terribly wrong. What kind of work do you do that. This is so. I mean, honestly, I feel like work romances are just, you know, unless there's some huge power dynamic, there's really nothing wrong with them. So.

[Caller]

I am an operations director for a smallish company, but I work very closely with the owner.

[Josh Radnor]

And can I ask, though, the owner, he's not married? He's single?

[Caller]

Yeah, he is single. He's divorced.

[Chelsea Handler]

Okay, so he's still single?

[Caller]

Yes.

[Chelsea Handler]

Okay. So I think you need to make your move, sister. Like five months. What do you do?

[Brad Dickers]

He can't make the move, right?

[Chelsea Handler]

He can't make the move. He's right. So you're gonna have to let him know how you feel and also give him an exit in case he doesn't have the same feeling. But you gotta do it. You're a woman. You have to be brave and be a woman. What if this is the love of your life.

[Caller]

I know.

[Chelsea Handler]

And honestly.

[Caller]

So I had told Catherine that I am divorced. I've been divorced for eight years, and never during this eight years have I found interest and not one person. And so my friends are just like, oh, my God, like, of all people, of course you're, like, in love with your boss. Like, why is this happening? But I'm just not brave. And I guess I need, like, more reassurance. I'm worried that our dynamic will change if for some reason it didn't work out, or I also don't want to be rejected. I don't know.

[Chelsea Handler]

But you got to get rid of the rejection part. That's part of life. And if you don't want to be rejected, then you. Then you almost don't deserve to be in love because you have to experience rejection. That's just the way it goes. You can't be afraid of it. It doesn't make you less of a woman. It doesn't make you less of a person. It doesn't make you less valuable. It just means that that person and you aren't a perfect match. That's okay. You're not gonna be a perfect match with most people that you meet.

[Caller]

Yeah, no, that's true.

[Chelsea Handler]

Can you do something cute, like slip him an email or slip a little note on his desk, Ask him to meet for a drink? Like, is there something that you feel more comfortable doing in order to just get the message across? Like, hey, do you wanna meet for a drink later tonight? I think there you'll get an answer to that real quick. That'll give you an indication also.

[Caller]

So he stopped drinking. And so that was one thing that we would. We would go do. We would go out for drinks or like, one time I was telling him how I love a martini, but I wanted to try the. The specific martini. Well, then all of a sudden, he brought all this stuff to make that. But, like, now he's not drinking, which is fine. But that kind of just changes the dynamic a little bit. And so that makes it harder. Cause I'm always like, let's just have a drink. But then also I'm like, okay, you're on your sober journey, so can I ask Josh here.

[Brad Dickers]

So you've been on a sober journey for a long time. Like, what's the dynamic of, like, asking somebody to go for a drink and you go somewhere that has five mocktails to choose from?

[Josh Radnor]

Yeah, I just get a bitters and soda or a club soda. Like, I like being in bars. I don't mind being in bars at all. You know, I think, like, in terms of being bold, something like, hey, I really like our dynamic. I really like the notes and the, you know, whatever you guys are doing and say, I don't want that to change. I was just wondering if we could maybe work in, like, a little bit of making out and just see what that's like.

[Caller]

That's all I want to do. I just want to make out with him.

[Josh Radnor]

Yeah.

[Caller]

And then we'll go from there. Just like, let me just make out with you one time. And then maybe he hates it, maybe I hate it, and then problem solved.

[Josh Radnor]

Right? But I think also there's a trick in creative writing where they're like. Like, I don't know how to start this story. And they're like, well, tell me the story. And then you tell them the story. And you're like, that's it. That's. That's how you tell the story. Like, that's how you write the story. So everything you said in the letter is like, I really like this guy, really like our dynamic. I just would really like to make out with him, but I don't know how to broach it. I think that's what you say.

[Chelsea Handler]

I love it.

[Caller]

Yeah. Because all my guy friends are like, he's giving you so much, and you're not responding to, like, the thing. Like, if he says something to me, like, today he was like, I'm wearing my favorite jeans that. They're vintage Levi's that I loved finding. And he's like, I like your. I like your jeans. And I'm just like. It's like. It's clear he's flirting with me, but I'm like, oh, thank you.

[Chelsea Handler]

Like,

[Caller]

I don't. I'm just.

[Chelsea Handler]

But just. You just need to go for it. Go for it. What's the worst thing that could happen? He could say he's not interested. It sounds like he is interested.

[Brad Dickers]

Yes.

[Chelsea Handler]

And he's. It sounds like he's not in a position to make a move on you because he is the owner of the business. So think about those two things and send him a cute note. Send him what? Josh said send him something like, I know you stopped drinking. Any chance you want to come and watch me have a drink? You could say anything cute. That's gonna be that. Even if it gets rejected, which is also a step towards getting closer to your goals, I believe. Even if this guy rejects you, I know you haven't been attracted to anyone in eight years. You will be again. You will Be. Hopefully this is the guy. But in case it. You know, like, you have to be. You gotta. You're stronger than that. That's silly. You know what I mean? Like, rejection is whatever. And there's a lot of flirting going on. So there's, like, proof in the pudding. And you need to capitalize on this moment, because what if someone else comes along and is willing to capitalize on the moment? Like, you gotta jump in there.

[Josh Radnor]

But also, like, rejection is good information. Cause you can move on with your life. Like, it's good to know. And also it's win, win the rejection. I think what Chelsea's saying is right.

[Caller]

Yeah. Yeah.

[Chelsea Handler]

So we're going to need you to do something and report back to us. Okay, I will. For sure. Okay. We're going to give you one week, and then you have to call Catherine and let her know what happened. Serious.

[Caller]

Leaving for Germany tomorrow. So he'll be gone for 12 days.

[Chelsea Handler]

Perfect.

[Brad Dickers]

Then today seems like a perfect time to do that.

[Chelsea Handler]

Actually, today does sound like a good day, because that would be great for.

[Caller]

He did ask me, how late can you stay at work? And I was like, like, all night.

[Brad Dickers]

Stephanie, he likes you.

[Chelsea Handler]

Yes. Stephanie, wake up and smell the cappuccino. Go be bald. It's very exciting that he's leaving for Germany. You could leave him with a nice makeout session right before he goes to Germany. And he's going to be thinking about you the whole time. Ding, ding, ding. This is your moment. Okay?

[Josh Radnor]

You got this.

[Chelsea Handler]

Okay?

[Josh Radnor]

We believe in you.

[Brad Dickers]

All right, go, Stephanie, go.

[Chelsea Handler]

Go, Stephanie, go. Bye.

[Caller]

Thanks so much. Bye.

[Chelsea Handler]

Okay, we're going to take a break, and we're going to come back and wrap up with Josh Radner. Planning a wedding shouldn't feel overwhelming.

[Brad Dickers]

The Knot brings everything together in one place.

[Chelsea Handler]

Vendors who get your vibe, a custom

[Brad Dickers]

planning checklist, guest list tools, and a

[Chelsea Handler]

free wedding website that syncs with it all. So instead of juggling a dozen apps and spreadsheets, you can actually enjoy.

[Brad Dickers]

Enjoy getting married.

[Chelsea Handler]

Get [e-mail] audio the knot. Let's plan your wedding together.

[Josh Radnor]

Protein is now at Starbucks, and it's never tasted so good. You can add protein cold foam to your favorite drink or try one of

[Chelsea Handler]

our new protein lattes or matcha.

[Josh Radnor]

Try it today at Starbucks.

[Chelsea Handler]

And we're back with Josh Radner, who has a new album called Eulogy Volume 2. Where can you download it, Josh?

[Josh Radnor]

Anywhere. You can download any music, I think.

[Chelsea Handler]

Music? It's like a podcast, guys. You can download it anywhere you get your music. He also has a podcast. He's the host of the podcast How We Made youe Mother. And he's as charming as possible. So now I know why we made out and didn't have sex. Josh, actually, because you are charming and. Yeah. And you. That was the right move.

[Josh Radnor]

I don't think if we'd had sex, I'd be on your podcast 20 years later. I think I. You'd be surprised I was being over.

[Chelsea Handler]

Yeah, you would be. I feel like we've had somebody that I didn't clock that I had sex with on. And then after, I was like, wait a second. But anyway, Josh, thank you so much for being here today.

[Josh Radnor]

It was great to be with you guys. Yeah. Always nice to see you. And thanks for having me.

[Chelsea Handler]

Yeah, absolutely. Have a great day.

[Josh Radnor]

Okay, Bye. Bye.

[Chelsea Handler]

Bye.

[Brad Dickers]

Thanks.

[Chelsea Handler]

Okay, guys, the High and Mighty tour is about to begin. I'm in D.C. february 13th, February 14th, Atlantic City, which I just added. 15th is Norfolk, Virginia. February 19th, Madison, Wisconsin. February 20th is Milwaukee, Wisconsin. February 21st, Detroit, Michigan. February 22nd, Ramah, Ontario. That's Canada. For those of you who don't speak Canadia. March 13, Cleveland, Ohio. March 14, Columbus, Ohio. March 15, Cincinnati, Ohio. And then March 20 is Denver, Colorado. March 27, Portland, Maine. March 28, Providence, Rhode Island. March 29, Springfield, Massachusetts. April 10 is Chicago. I'll be at the Chicago Theater. April 11, Indianapolis, Indiana. April 12, Louisville, Kentucky. April 16 is Albuquerque, New Mexico. April 17 is Mesa, Arizona. April 23 is Kansas City, Missouri. April 24 is St. Louis, Missouri. April 25 is Minneapolis, Minnesota. April 30, Nashville, Tennessee. May 1 is Charlotte, North Carolina. May 2 is Durham, North Carolina. May 6, I'm doing Netflix is a joke festival. I will be in Los Angeles. That is a new announcement. And May 15th, Saratoga, California. May 16th, Monterey, California. May 17th, Modesto, California. And then June 4th, Portchester, New York. June 5th is Boston, Mass. And June 12th is Portland, Oregon. And then Seattle is June 13th. So suck on that. Everybody. Go to chelseahandler.com for tickets.

[Brad Dickers]

Do you want advice from Chelsea? Write in to dearchelseapodcastmail.com Find full video episodes of Dear Chelsea on YouTube by searching earchelseapod. Dear Chelsea is edited and engineered by Brad Dickers executive producer Kathryn Law. And be sure to check out our merch@chelsea handler.com. Spring just slid into your DMs. Grab that boho. Look for that rooftop dinner, those sandals that can keep up with you. And hang some string lights to give your patio a glow up. Spring's calling Ross, work your magic.