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Kathryn Law
This is an I Heart podcast.
Chelsea Handler
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Chelsea Handler
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Chelsea Handler
You know how some people meal prep their dog's food? Yep. Not in my house. I can barely prep my own meals that don't involve tequila. And that's why I love just fresh from just food for dogs. Real human grade food with no fillers, no preservatives and it's shelf stable. No fridge drama. Easy to travel with. And Doug eats like he's at a steakhouse. His coat's shinier, his energy's always up and honestly, he eats better than most men I've dated. Now get 50% off@justfoodfordogs.com this is Chelsea Handler from Dear Chelsea. I just announced all my tour dates. They just went on sale this week. It's called the High and Mighty Tour. I will be starting debuting my new material. Well, I've already started debuting my new material, but in an organized tour form in February of next year. So I'm coming to Washington, D.C. norfolk, Virginia, Madison, Wisconsin, Milwaukee, Wisconsin, Detroit, Michigan, Cleveland, Columbus, and Cincinnati, Ohio. Denver, Colorado, Portland, Maine, Providence, Rhode Island, Springfield, Massachusetts, Chicago, of course, Indianapolis, Indiana, Louisville, Kentucky, Albuquerque Mesa, Arizona, Kansas City, Missouri, St. Louis, Missouri, Minneapolis, Minnesota, Nashville, Tennessee, Charlotte, North Carolina, Durham, North Carolina. Saratoga, California. Monterey, California, Modesto, California, and Port Chester, New York. Boston, Massachusetts, Portland, Oregon, and Seattle, Washington. I will be touring from February through June. Those are the cities that I'm in. Pre sale started last week, so tickets are flying. I haven't added second shows yet, but we probably will be to some of these. So go get your tickets now if you want good seats and you want to come see me perform. I will be on the High and Mighty Tour.
Kathryn Law
Well. Hi, Chelsea.
Chelsea Handler
What's up? What's up? I had a photo shoot yesterday for the COVID of Snow magazine, which is like a ski magazine, so I had a cover. So I was like, oh, good. I don't have to worry about my body at all because I'll be in ski clothes. And then I woke up. I was so excited. I'm like, yay. I just get to have to be smiling, get a puffy thing. Yeah. And then I looked at the mood board for the photo shoot, and guess who's in a bathing suit on skis. Yeah. Yeah.
Kathryn Law
I can't have your skin.
Chelsea Handler
I know. I know. I can't have. How can I? What am I gonna say to that? I don't do that. So then I was like, oh, fuck. So I texted my makeup artist, and I was like, bring body makeup, obviously.
Kathryn Law
Lots of contouring on your ass.
Chelsea Handler
Contouring everywhere. I was like, I have cellulite in places that are not cute.
Kathryn Law
You're not used to.
Chelsea Handler
Well, no, I'm used to it. I've had it for a long time. But it's like, you know, like, you can prep yourself. I don't know. It was just. It ended up being a great photo shoot. The photographer was there.
Kathryn Law
Great.
Chelsea Handler
And the first thing he said to me was, I know you like to take your time. And then we all burst out laughing because clearly he got the memo that everything is as fast as possible and as quick as possible. And that's how I like sex, too. Let's go. Hurry up. So it was actually ended up being a really good photo shoot. I got some hot photos out of that, hopefully. I mean, if not, they'll just have to retouch them.
Kathryn Law
Yeah, I mean, that's easy.
Chelsea Handler
I'm not against that.
Kathryn Law
Just as long as they don't use AI and give you seven fingers on one hand.
Chelsea Handler
I saw another bad AI this morning. Looks like AI is having a meltdown.
Kathryn Law
Truly.
Chelsea Handler
There was a big AI that came out last week. Week. Right. That got panned because it was giving misinformation about former presidents and the states, the names of states. Like it was basic information. So it was like, sounded like it was crashing. But I still don't even really understand AI. And I do. It does help me a lot with my Spanish.
Kathryn Law
Oh, that's right.
Chelsea Handler
I mean, more than my Spanish instructor. Like when I ask AI to break down the difference between, like, kedar and, you know, another verb, guardar, because I don't understand the difference. It will really. I'm like, oh, this is good info.
Kathryn Law
Ah, that's good.
Chelsea Handler
But I try not to use it because I heard that every time you use it, you know, you're basically like killing, you know, a farm, 17 trees. Yeah, yeah, yeah.
Kathryn Law
When I try, this is actually good for people to know because I don't like to use it either. And Google sort of automatically makes you do it now. So if you don't want to use AI, you can type your search in like, why are my tomato plants dying? Which is what I typed in recently. And then you do the little minus sign and AI. So you type in your search minus AI and it won't give you AI answers for Google.
Chelsea Handler
Yeah. And Chrome.
Kathryn Law
Yes, I think in Chrome too.
Chelsea Handler
I don't know. I don't know what the difference is really, but yeah, minus AI. I see. Because it's always says AI generated, right?
Kathryn Law
Yes, exactly.
Chelsea Handler
Okay, well, that's good to know. At some point you're going to have to explain to me what Reddit is and substack, because I somehow am a member of substack, but yet I've never joined.
Kathryn Law
I actually think that I'm prepared to do that right now.
Chelsea Handler
Oh, okay, great. I am. You mentioned Reddit the other day during an interview and you're like you're all over Reddit to someone. And I was like, what? I know, of course I heard. I've heard of Reddit, but I'm not on it.
Kathryn Law
So I will say I didn't start using it that much until recently. But basically Reddit is almost like people can go in and post their opinions or ask questions and like other people will comment on it. So to use the same example, like I can go in and say like, hey, why? Why are my zucchinis not growing properly? And I'll have 17 people be like, oh, you need to use this kind of fertilizer or you need to water them more and they're not getting enough sunlight. So it's like real people answering your questions. And I'm finding it really helpful in the age of AI because half of the time an AI answer is wrong.
Chelsea Handler
Right?
Commercial Announcer
Is it?
Kathryn Law
That's right.
Chelsea Handler
Well, I mean, my cousin told me that Google's wrong too. Like that Google's just an aggregate of all this information so that sometimes it gives you correct information and then sometimes it just gives you random information.
Kathryn Law
Yes, that is true. But I find AI is like kind of just going and getting random stuff and like putting a little synopsis and it's like 50% of the time it's not true, I find. So this is actually real people answering.
Chelsea Handler
Your question, which could also not be true.
Kathryn Law
That's true.
Chelsea Handler
They are the ones. Yeah, you have to take a little.
Kathryn Law
Bit with a grain of salt. But it's also there's a dark side of Reddit where there's like all kinds of bad stuff. You don't want to go on that side of Reddit.
Chelsea Handler
What is like what?
Kathryn Law
Like, I don't. I mean, like nasty porn and stuff. Like not normal porn, like not good.
Chelsea Handler
Why can't there be one platform that's just good and nice?
Kathryn Law
I don't know.
Chelsea Handler
Why does everything go to shit? That's why I'm scared of AI so much. Because it's like, of course there's going to be good stuff that comes out of it. There's going to be so much bad stuff that comes out.
Kathryn Law
So much bad stuff.
Chelsea Handler
When I heard on that. Yeah. That they have self preservation, I was like, oh my God.
Kathryn Law
That they were the bad guys.
Chelsea Handler
That has basically been engineered now to, to understand. Well, not intentionally, but to understand that if you're shutting down a system and replacing it with a higher performing, more nuanced system or more comprehensive system, it will fight to remain alive. Like a fucking alien. Like World War Z or like the Terminator.
Kathryn Law
I know we've had these movies before.
Chelsea Handler
We should have known better. Yeah, we did. And that's where we got all these ideas. I mean, talk about stupid and stupid.
Kathryn Law
Well, you know what, on that note, let's have a little bit of a nice transition into a nice Response we got from a listener. I can say nice a few more times if we need to. So Deanna called in on our Rachel Bloom episode several months ago and she had lost a beloved dog and you advised her to get a new one stat. So she said, oh, I forgot Doug.
Chelsea Handler
Oh shit.
Kathryn Law
Is he at home, I hope.
Chelsea Handler
Yes, I forgot to bring him. Oh my God. No, I forgot. I meant to bring him today anyway. Okay, go on.
Kathryn Law
That's okay, because one of our guests that we're recording with today is actually bringing her dog. So we all have a dog. But she said we did take Chelsea's advice. We met and picked up our new lover today. His name is Jupiter. We love hiking the mountains together. She's in Colorado. The advice really helped and made us feel much less made me feel much less alone in my grief. All the best, Deanna.
Chelsea Handler
That's cute. And then for a nickname, Jew. I mean, that'll work out nicely. Excellent. Perfect. Great.
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Chelsea Handler
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Chelsea Handler
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Chelsea Handler
You know that feeling when you come home late from work and those puppy dog eyes just pierce right through your soul? Or when you're packing for a trip and your cat refuses to leave your suitcase? Yep, we've all been there. Pet parent guilt is real. And you know what? It's completely normal. That's exactly why Hill's Pet Nutrition exists. They understand that being a pet parent means being human. With all of our imperfections and daily juggling acts, Hill's science led nutrition helps you give more love than humanly possible. Whether it's those long work days or trying to balance attention between multiple pets. Hill's Pet Nutrition gets it. They've created science based nutrition that supports your pet's lifelong health so that you can feel confident even when life gets hectic because you're only human. There's Hills. Science does more. Ready to let go of the guilt, Find the right food@hillspet.com iheart that's hillspet.com iheart com.
Kathryn Law
Okay, so we do have a question from a caller and I think this is specifically a really good question for you. So Rocio is calling in from Rome.
Chelsea Handler
She Rome.
Commercial Announcer
Rome.
Chelsea Handler
Wow. How did we work that time difference out?
Kathryn Law
You know what actually like our pre interview call was dangerously middle of the night for her but this one is like early evening. So her subject line is should I fake a psychedelic trip? Dear Chelsea, my name is Rocio and I'm a 46 year old single woman writing to you from Rome. I need some advice and couldn't think of anyone better than you for this one. I don't drink alcohol, never have. I don't smoke, don't even drink coffee for that matter. I just have never been interested in any of it. I think it's mostly because I'm autistic. Diagnosed about 15 years ago, I've done my work in therapy and can say I'm very happy where it has all led me. I do still have some issues with OCD and letting go of control. Some years ago a friend of mine, also autistic, suggested I take MDMA to help me with that. I considered it for a long while but never got myself to do it back then. Well, three years ago I was with a childhood friend who now lives in Barcelona. He had just broken up with a boyfriend and was sad and alone in Amsterdam, so I hopped on a plane and joined him there for a couple of days. It was there that he proposed we take MDMA together and without overthinking it too much for once, I just did. For anyone who has experienced it, you know how amazing your first Molly trip can be. From that day on, me and my friend decided we would trip together and help each other sort out our personal difficulties. We trust each other and feel safe sharing our innermost thoughts without being judged. And so it began. Every three months he would come to Rome or I would go to Barcelona for our spiritual retreats as we call them. We do this indoors at home with our chill music and it's done miracles for us. Truly life changing. About six months ago I switched things up a bit by introducing LSD into the picture. It blew our minds. If Molly had helped so far, then LSD just took us to a whole new level of awareness. The thing is Chelsea, we are talking big doses here, not microdosing. The last trips have left me feeling physically off and it takes me days to recover. I'm also at a point in my life where I feel the very best I've ever been. Everything is perfect and I'm aligned just right. I have an amazing life, a job I love, and loving friends and family. I think I've done lots and lots of soul searching and acceptance thanks to those substances, but I think for now I'm done with them. My friend is coming soon for our next scheduled trip at my place. I'm really not feeling it this time. I don't have the excitement I usually get when the day of the trip approaches. I'm at a crossroads and don't know whether I should just tell my friend. I don't Want to do it and be a party pooper? Or maybe I should just fake it. Yes, you heard right. I'm thinking about faking the trip. As women, we know pretty darn well how to fake many things. I know that if I tell him I don't want to do it, then he just wouldn't want to do it alone. For him, it's either we do it together or nothing. He's been really looking forward to it and counting the days. And I know not being truthful about it is not nice, but I do it just because the arrangements have already been made. I just don't know. Am I overthinking? And should I just trip with him? Should I explain and be a party pooper? Should I just fake it and let him have his trip? Chelsea, please help. Rocio.
Chelsea Handler
Hi, Rocio.
Rocio
Hi.
Chelsea Handler
Hi. How are you?
Rocio
Fine, thank you. I'm so excited about this advice you're about to give me, because I'm really lost here. I thought this was such a perfect question for you, so.
Chelsea Handler
Oh, it is a good question for me. Right on. Right on the money. First of all, I would always advise that if you don't feel like doing a drug, do not do it. You have to be in the right head space to do a drug. You do not need to lie to your friend. Your friend is gonna understand that you're not in the mood to do it. If you've done. You found something you loved, and it sounds like you really went for it enthusiastically, like, with great intentions of having a great journey, and you've accomplished that, and then you kind of took it farther and farther. Or I should say further and further. But you don't need to push things like that. Like, that's what we get. We get greedy with the results of things. Right? We like something the way it affects us. We want more of. It's like that dopamine hit of something really clicking. But I would say, like, just a don't worry about your friend making arrangements. You guys have been through all of this stuff together. He's definitely going to understand that you don't want to do it. And he's most likely going to opt to not do it and spend your time together in a different way and, you know, have some backup plans ready. You're in Rome. You have a million things you can do, right?
Rocio
Yes. Yes. No, for sure. I mean, I was also worried about our friendship. We're friends from childhood, but in the last few years, it's only been about the trips.
Chelsea Handler
Right? I hear you.
Rocio
I'm so afraid that if I take this element out, that he will feel like, I don't know, betrayed or something, or that we won't. That it won't be as deep as it has been so far.
Chelsea Handler
No, that's you being a woman and being hard, scarred by the world because you don't want to disappoint anyone. That is being a woman, that is like the badge that we wear, and we shouldn't. It's not our responsibility. You have to take care of yourself first and foremost and your friend. Honestly, if he got there and you were like, listen, I mean, you could tell him beforehand just to be like, listen, I know that things are planned, but I just have to tell you, I'm not feeling it this trip. If you want to go ahead and do it without me, I'm totally down with that. Or we can hang out and to not do it this time. Like, I guarantee you he's going to be down for that and just be very honest about it. And if he really isn't okay with hanging out with you without tripping, first of all, that's a whole new adventure that's gonna be a high of its own, because you guys haven't done that yet. And if he isn't okay with that, well, then kind of like, that's not really your friend anyway. It sounds like it was a drug friend. So I really just think you need to be true to yourself, your feelings, your emotions. Be a woman and think of all other women when you make decisions for yourself.
Rocio
Okay.
Kathryn Law
And I wonder if there's, like, something you can do that's not drugs, but, like, gives you sort of a very novel experience or an endorphin high. Like, I mean, I don't know if there's, like, bungee jumping in Rome, but, like a helicopter ride or like, something that's, like, maybe a little touristy and. And really fun, but something that's gonna, like, give you that flood of endorsements.
Rocio
I mean, because he's, like, very, like, hyperactive and everything, and I'm very mellow. I'm very. I'm like a lone wolf, you know, I'm always in my space and everything. So we complement each other very well because I need to explore more, you know, like, the world in general, and he needs to calm down. So that's, like, a really nice dynamic we've always had. So by tripping together, I've been able to open up more, and he's been able to have, like, less FOMO and, you know, like, be in the moment and everything. So, yeah, I mean, I think I'm definitely ready to let go of that phase. You know, I've took it, as Chelsea said, very. As far as I could. You know, we went every time like it was a crescendo. And honestly, it would have been fine not taking all these heavy doses, but also then I was trying to please him, and he's like, let's take more. Let's take more. And it just got to a point that it's not enjoyable anymore.
Chelsea Handler
No, no, no, no, no, no, no, no. You overdid it. And you have to be. You have to honor yourself.
Kathryn Law
Okay, well, it sounds like you got to the place where. What you were looking for from this, you know, experiment and from this adventure. You got to that point, you know, you're. You're loving life. You feel refreshed and like you don't need to do it anymore unless you, you know, get a hankering down, down the road.
Rocio
No, I. Yeah, I just. I mean, Chelsea's right. I. I think it's just. I'm just afraid to disappoint him or, like, leave him behind, so I'm trying to please him or, like, fake that I'm still at the point where he is at, but I know I've outgrown it, you know, so. Yeah, well, that's great advice. I have to be honest and.
Chelsea Handler
And let him know before he makes the trip so that he doesn't get mad at you for not telling him.
Rocio
Before he got on the plan before. Yeah, yeah, just let him know.
Chelsea Handler
Go. I still want to hang out. I think we could figure out thing. You can even, like, catalog all, if you haven't done this already, and maybe you have catalog all of your journeys or trips that you've done together. Maybe you could do like a review, you know what I mean? Of everything. Like a full scale review of everything. And really talk about the first time, the second time. What's changed for you? What's changed for him? Like, another way to, like, kind of, you know, have some growth and, like, expansion, but without using the drugs.
Kathryn Law
I love that. Or even you could see like a shaman or go get Reiki or do something else that sort of, you know, have a sound bath, something that's spiritual.
Chelsea Handler
I don't know about a sound bath. I think that might be disappointing after an acid trip, but whatever.
Kathryn Law
I've never done acid, so it sounds great to me.
Rocio
Okay, well, that's great advice. Thank you very much. I was really lost with this one, so.
Chelsea Handler
Okay, well, yeah, you take care of you and then your friend will take, hopefully will take care of you too in the same way. But yes, please look out for yourself. Okay. Thank you for calling in. Nice to meet you.
Rocio
Thank you. Bye.
Chelsea Handler
Bye. Okay. And well, that was our minisode for the week, Katherine.
Kathryn Law
All right, well, we'll see you guys.
Chelsea Handler
I feel minnied. Okay. Okay. Bye guys. Bye.
Kathryn Law
Do you want advice from Chelsea? Write into dearchelseapodcastmail.com Find full video episodes of Dear Chelsea on YouTube by searching earchelseapod. Dear Chelsea is edited and engineered by Brad Dickert executive producer Kathryn Law. And be sure to check out our merch@chelseahandler.com.
Chelsea Handler
You know that feeling when you come home late from work and those puppy dog eyes just pierce right through your soul? Yep. We've all been there. Pet parent guilt is real and completely normal. That's exactly why Hill's Pet Nutrition exists. They understand that being a pet parent means being human. Hill's science led nutrition helps you give more love than humanly possible. Whether it's those long work days or trying to balance the tension between multiple pets. Hill's Pet Nutrition gets it because you're only human. There's Hills. Science does more. Ready to let go of the guilt? Find the right food@hillspet.com iheart that's hillspet.com.
Commercial Announcer
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Chelsea Handler
New users get a 100% bonus on their first purchase. Up to $100.
Commercial Announcer
No purchase necessary. Legends International void where prohibited by law 18 years or older. Terms and conditions apply.
Chelsea Handler
You know how some people meal prep their dog's food? Yeah, not in my house. I can barely prep my own meals that don't involve tequila. And that's why I love just fresh from just food for dogs. Real human grade food with no fillers, no preservatives and it's shelf stable. No fridge drama, easy to travel with. And Doug eats like he's at a steakhouse. His coat's shinier, his energy's always up and honestly, he eats better than most men I've dated. Now get 50% off@justfoodfordogs.com this is Amy.
Amy
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Kathryn Law
This is an iHeart podcast.
Podcast: Dear Chelsea
Hosts: Chelsea Handler & Kathryn Law
Date: October 3, 2025
This minisode of Dear Chelsea brings Chelsea Handler and Kathryn Law together for their signature blend of candid advice, humor, and relatable discussion. The episode centers on listener questions, focusing primarily on a heartfelt inquiry regarding personal boundaries in friendships, especially when they’re rooted in shared psychedelic experiences. The hosts also touch on topics like AI, social platforms, and memorable listener follow-ups, all with their typical wit and authenticity.
[03:52 – 08:49]
"type your search minus AI and it won't give you AI answers for Google." – Kathryn, 06:10.[06:29 – 08:49]
[08:49 – 09:52]
[13:19 – 21:54]
| Timestamp | Segment Description | |-----------|----------------------------------------------------------------------------------------| | 03:52 | Chelsea talks about her photo shoot and body confidence | | 05:17 | Discussion on AI mistakes and language learning | | 06:10 | Kathryn shares AI search workaround | | 06:29 | Chelsea asks for an explanation of Reddit and Substack | | 08:49 | Listener Deanna follows up about adopting dog “Jupiter” | | 09:40 | Chelsea’s joke about the “Jew” nickname | | 13:19 | Rocio’s dilemma: faking a psychedelic trip with a friend | | 16:32 | Chelsea gives core advice to Rocio | | 17:54 | Chelsea reflects on women's reluctance to disappoint | | 18:53 | Kathryn suggests alternative experiences to tripping | | 21:05 | Chelsea recommends a review of past journeys | | 21:54 | Chelsea’s closing encouragement for self-care |
The episode keeps the tone warm, sharply funny, and honest. Chelsea’s signature irreverence shines through even as she gives deeply empathetic, practical advice about tough friendship dynamics and boundaries. The rapport between Chelsea and Kathryn brings out real-life relatability, and the inclusion of genuine listener stories rounds out the show’s signature blend of comedy, candor, and heart.
Perfect for listeners craving a blend of laughter, relatable confessions, and reassuring advice with plenty of real talk.