Dear Chelsea - Gold Star, Not Platinum with Andrew Rannells

Episode Date: May 18, 2023

Chelsea is joined by Andrew Rannells to discuss therapists who quote Barbra Streisand, the trouble with sleeping with your “straight”, married co-star, and why falling in love on-set is just so typical.  Then: An older man wonders if he should open his younger partner up to more variety.  A Portlander just can’t seem to get over his ex… or his ex’s dog.  And a 40-something with a broken picker needs help finding love that doesn’t hurt so much. * Need some advice from Chelsea? Email us at [e-mail] * Uncle of the Year by Andrew Rannells Too Much Is Not Enough by Andrew Rannells * Produced by Catherine Law Edited & Engineered by Brandon Dickert * * * * * The views and opinions expressed are solely those of the Podcast author, or individuals participating in the Podcast, and do not represent the opinions of iHeartMedia or its employees.  This Podcast should not be used as medical advice, mental health advice, mental health counseling or therapy, or as imparting any health care recommendations at all.  Individuals are advised to seek independent medical, counseling advice and/or therapy from a competent health care professional with respect to any medical condition, mental health issues, health inquiry or matter, including matters discussed on this Podcast. Guests and listeners should not rely on matters discussed in the Podcast and shall not act or shall refrain from acting based on information contained in the Podcast without first seeking independent medical advice.See omnystudio.com/listener for privacy information.

Joel, the holidays are a blast, but the financial hangover, that can be a huge bummer. If you are out there and you're dreading the new statement email that reveals the massive balance that you may have racked up, well, you could use our help. That's right. I'm Joel. And I am Matt. And we're from the How To Money Podcast. Our show is all about helping you make sense of your personal finances so you can ditch

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my people, what's up? This is course love, man. I cannot believe we're already wrapping up another season. Of course, love Supreme, man.

We've got some amazing guests lined up to close out the season, but you know, I don't want any of you guys to miss all the incredible conversations we've had so far. I mean, we talked to A. Marie, Johnny Marr, E., Jonathan Schechter, Billy Porter, and so many more. Look, if you haven't heard these episodes yet, hey, now's your chance. You've got to check them out. Listen to Questlove Supreme on the iHeartRadio app, Apple Podcasts, or wherever you get your chance. You gotta check them out. Listen to Questlove Supreme on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hi, Katherine.

Oh, hi, Chelsea. Hi, what's going on? I just got back from Mexico. Oh, and is it? It's still lovely. It's still wonderful. I go every year for this girls trip with two of my best girlfriends. I leave my husband at home.

This time there were three dogs to take care of. So he's slightly resentful, but has forgiven me for abandoning him. just tell him to shut the fuck up. Honestly, slightly resentful. Whose sperm made those dogs? His.

Absolutely. Exactly. No, but he did great with the pups while I was gone. And I just hung out and played with my girlfriends and ate a lot of tacos. And it was great. I like Cabo. Yes, yes. Actually, I'm going to Cabo a little later this year.

Oh, my God. Look at you. You're like just a regular globetrotter. Where are you going next? I have a lot of vacations lined up this summer. I'm going to be all over. I'm going to be globet up this summer. Yes, you do. I'm going to be all over. I'm going to be globetrotting. I'm going to London.

I'm going to Spain. I'm going to Africa. My sister and I are going to become lesbians. My dream for us to become a unit is finally happening. She can't resist my advances anymore. The other day, she sent me a property and said, what do you think about buying this together? I was like, oh, here we go. There it is.

I was like, oh, here we go. There it is. I was like, it's starting. She's starting to capitulate to the fact that we are going to be long lost lovers. Oh, fantastic. Which one is it that you're taking as your lover? Simone is, I am taking her as lover. Shoshana's married. Simone's not.

Okay, of course. But yeah, she, it was funny because when we were in Maine a few years ago, my brother, Roy, I think I mentioned this before, wanted to. I was like, oh, look, we could all get a compound because like eventually I just not eventually for climate change. I want to buy like 100 acres either in Maine or northern Canada, somewhere along those lines. And I was like, we can all have our different houses and, you know, on the property and then have a main house. Like this is exactly what I wanted to do up to. Just live with it in a commune. Yes, exactly. That you built yourself and it's

beautiful and. And it stays above water. Yes. You know, I'm climate paranoid now after reading all the things that I've read. So I have had to pivot my reading material. You guys, I performed at Red Rocks last Wednesday. Oh my gosh. And it was the most epic night, one of the most epic nights of my life. Well, you posted that you were the first woman to ever headline there? Female comedian. First female comedian to ever headline there. Yeah, I know. That's crazy. I was like, hello, welcome to the future. Anyway, that was so fun because I woke up Wednesday and Red Rocks is a huge show. There's like 8,000 people there. So I get a text from my manager or agent and they're like, okay, it's pouring in Colorado. Bring warm clothes. And I'm like, well, what do you mean it's pouring?

This is an amphitheater. Like, how do I perform in the rain? And they're like, oh, rain or shine, it goes on. I'm like, but it's calling for Lunder. I mean, Lunder. You guys, it was calling for Lunder. Not Lunder. And I was like, people could get electrocuted with Lunder.

And they were like, no, no, they have a whole system in place. They have a meteorologist that works at Red Rocks that tracks the storm. Like if it's actually too unsafe. Yeah, if it's like three miles, within three miles of the venue, I learned that they will call off the show. Anyway, I went. My sister Simone came. My bestie Sophie came. A bunch of people were there.

And my agents and managers all came out because it was just going to be one of those nights. And I never look at the stage before I go on stage. I just don't. But this is something else. That's not my thing. But because it was raining, I went out and I was like, I just want to see where the roof stops over the performer. Are you getting rained on? What do I need to be wearing out here? Because I had my hair done. I had, like, the extension pieces in, like, you know. And then I saw the stage, and the person who was performing was just getting soaked. Oh, no. And I was like, wait, what? So then I went in the bathroom, ripped out all my hair pieces, put my hair in a ponytail,

rolled up my sleeves, and I was like, bitch, you need to get your head on straight. Oh, my gosh. Because you are basically going to be walking around in the rain. And so you also got rained on. Well, yeah, but it wasn't as dramatic. I mean, it was dramatic for the audience members because they're the ones that sat there and they said, you don't understand Coloradans. Because I said, I'm not performing to a half empty, you know, we sold tons of tickets for this. I don't want to perform to a half empty house. And they were like, no, Coloradans are used to it. They'll just put on a coat. And I can't tell you how electrifying the whole night was. And almost getting, I mean,

it was electrifying with no one getting electrocuted. So that was nice. But I was on such a high. And it was so funny. I got home. You know, we were all drinking, having a little after party. I had friends that came from that live in Colorado. We're all out backstage after we go, we go to the, the hotel, you know, it's so much fun and we're just such a celebratory mood. And I'm lying in bed going to sleep going, Oh, I'm so happy. No one's in my bed right now. That was the last thing I said as I was falling asleep. I was like so happy. And then I was just thinking, I'm so happy I get to celebrate this alone. You get it all to yourself. But then it was a real pivot because we flew from Denver to the next night. I was in New York City. The next night, I played the Catskills.

So that was quite a transition from Redbox. Catskills was awesome. Then I went to Bangor, Maine, and then I went to Wallingford, Connecticut. So they were all very great shows. So I just had a great week. And then this weekend, I'm performing at Graceland. Oh, my gosh.

Yeah, I'm doing three dates in Tennessee, like Chattanooga, Memphis and some some other Knoxville. Yeah. I've heard Chattanooga is beautiful. I've never been, but I've heard it's wonderful and like mountainy and all that stuff. Well, good. I hope I hope I see that because, you know, Tennessee is on my hit list right now. I'm not happy with their politics. So it's very hard for me to go to these places, even though I know my presence is necessary. It's needed. It's needed. And we get emails all the time, too, about like, wait, no, but please come to these places that are trying to keep you out or like trying to change the laws and all this stuff. Yeah.

I'm getting a lot of DMs on Instagram and a lot of comments about my Florida comments about not visiting Florida. But I have to say, guys, the only way to make a point in any place in this country is economically. And even though I'm only one person, I hope other artists will follow because it's just unacceptable what he's doing down there. He's disgusting, absolutely disgusting politics. Now he's trying to ban books from the Holocaust. He's took away any sort of affirmative action program they have for universities. I'm not sure what the wording is for Florida because it's not called affirmative action down there. I'm sure they got rid of that language a while ago. So it's just it makes me so sick to my stomach as it should to every American. The Daily did a really interesting episode about how Tucker Carlson is like literally in Florida, they're taking keys from his playbook. And when he flew all those migrants to Martha's Vineyard, that was something that Tucker Carlson had said on the air.

And then he went ahead and did it. Yeah, well, I read an interesting article also about Rupert Murdoch on Vanity Fair. I guess it was last month. I don't know. It was in my hotel room. But it was amazing about the dynamic with his family and basically how succession is mimicking the whole, he plays the kids all against each other. And he had lunch with Ron DeSantis and his wife about a year ago and said, if you are the Republican nominee or if you want to run for president, you have our backing.

Because now Trump and Fox are at a crossroads. They're not really. But I don't believe any of these people because of what happened last time. The minute he gets the nomination, they're all going to turn around and be like, OK. Because I'm asked. They'd be willing to take that over, you know, another Biden administration, of course. And Biden administration, I don't have a lot to say about that either. Like, I'm for a lot of the things that he's done. But I understand that he's also 117 years old.

And that's not going to get any young people excited. Right. I will say it has been very nice to just not have to think about the president for a couple of years. I know. It's so nice to not have to think about that stuff. Yeah. Brad has been rewatching Parks and Rec and it's this very hopeful time before 2016. And man, it was a real it was a much simpler time. You're reminded of like how how maybe foolish we were and hopeful we were that like things were just gonna

keep getting better for everybody. Yeah, I'm not gonna participate in the way that I did last time by watching the news on ad nauseum. I'm not going to let, I'm not going to listen to Donald Trump speak. I can't take it. It is too upsetting and I'm smarter and wiser now and we have to focus on,

I don't know what we have to focus on, quite frankly. I mean, it feels slightly, you know, hopeless. And I don't ever want to, I don't ever want people to listen to me and feel hopeless after. So we're just going to remain positive and know that the world is a cyclical place. And there are good times and bad times. And let's just enjoy the time that we're in now. Yeah. And voting still matters, you know. And let's just enjoy the time that we're in now. Yeah. And voting still matters, you know, and we do what we can to move toward a better tomorrow, as they say. And on that very special note, we have a very special guest.

We do. You know him. He's in everything. I first saw him in the Book of Mormon on Broadway. He's had a book called Too Much Is Not Enough, and now he has a new book out called Uncle of the Year. Please welcome Andrew Rannells. Andrew, did we fucking wake you up? No, I was just late. It's almost 2.30 here in New York. So you were sleeping from last night still? No. I'm so sorry. Chelsea Handler. That's me. Hi. I'm so excited to meet you.

Hi, and I'm Catherine Law. This is Catherine, my co-host. Hi. Hello. How are you? I'm just great. Well, congratulations, Andrew, on your book. Well, thank you.

You know how hard it is to write a book and then distribute a book. It's a tricky situation. It's a lot of work to put out a book. Yeah. And I'm very proud of this book. I wrote one a couple years ago, and that one seemed to sort of come out a little bit easier in some ways. This one was a little harder to talk about and a little harder to share, but I'm very excited to get to share it. You know, the weirdest part of it was doing the audio book. Yeah. I don't know if you had this.

I find that to be incredibly annoying. Well, I wrote it and I did all of the stuff and I feel like I really processed all of my thoughts. And then I had to read it out loud in front of a weird stranger, an engineer, who had not read it, by the way. But gives you notes on your performance and hasn't read the book and has never met you.

Yep. And he was like, it doesn't sound like you. And I was like, I'm sorry, what now? It doesn't sound like me. Okay. I had a guy go talk more slowly. I go, no, that's not how I talk. Yeah. It was very strange, but I'm happy with the way it all came out. But man, oh, man. So why do you think that this experience or the second book for you was more difficult than the first? I feel like the first book was a little more linear. It was a little more about like how I started into showbiz and like it felt like a little more natural progression. This one is more about more adult stuff, I guess. It all kind of started because I wrote this essay for the New York Times

about my anxiety and it's much more personal. Can you talk a little bit about your anxiety experience? Because I know you started therapy because of that. And then, you know, it wound up being a very good thing for you because of other things that happened in your life. I've had many therapists over the years. Some of them are great. You know, therapists are, it's hard to find a good one sometimes. I really struggled during the pandemic. I've been very lucky as an actor. I go from job to job to job. And then I had a really hard time not working. And it was really hard to like stop and slow down and figure out, well, who are you if you don't have a job? And that was a really tough thing to figure out. And very relatable, since everyone was pretty much out of a job at the same time. Yeah. Even though it feels isolated, like it's happening to you. I mean, in reality, it is happening to the whole world. Everyone sort of had that feeling where like the bottom just sort of dropped out and you had nothing to do. And I thought maybe

I could relax into it, but I couldn't relax into it. I see. Yeah. And that was, I thought maybe like, well, nothing's happening and everyone's on the same page and it's totally fine. I couldn't get on board. Well, and there is a sort of thing where, you know, our identities get wrapped up in what we do. It's the thing we spend 10, 12 hours a day doing. We say, I am a actor, podcast producer, whatever. That's what I do. So it's difficult when you have to separate those two things. It's hard to balance the act of your consciousness, like spirituality with your reality sometimes. It's really hard to be the person you want to be in a stressful situation sometimes. And then you're like, fuck, wait, I thought I would be able to handle something like this better. Not that anyone had, you know, any idea the pandemic was coming, but. No, but it is, that's a very good way to say it. It's like, I thought maybe I could handle

myself better. Yeah. And I think with therapy a lot, you, did you go to therapy before the pandemic as well? Yes. Sure. Yeah. Yeah. No, I've had, I mean, like off and on for, you know, 25 years I've had a different, yeah. Yeah. I know from my own experience that you have this idea sometimes when you go for a long enough period of time that you're fixed and there shouldn't be another issue. Like for me, I'm always like, okay, I sorted all of that out. I shouldn't have to face anything like that again. And so then when you're faced with it again, and you may act in a seemingly similar way, you're definitely like there's self-flagellation involved because you're like, fuck, I already learned that lesson. What am I doing this again for? Why did I do it differently? Yeah, I've had many different therapists. I had a therapist that I went to for many, many years.

And I realized, I sort of hit a wall with this therapist. And I realized when I hit the wall, he sort of like, I was telling him a story and he sort of like glassed over it a little bit. Like I could, I could tell he wasn't listening. And then he said to me, Andrew, what's too painful to remember? It's simply hard to forget. So it's the laughter we remember. And I said, did you just quote the fucking way we were to me and he said oh god i'm so sorry i i guess i did i said you quoted the way we were to a gay man and i wouldn't catch it was he gay because he is now he's now gay he was not gay but i was like how could that happen that's so funny and so annoying possibly say that right i've had moments like that with people when

they've said something i'm like that's the end that's the end of our friendship you just crossed the rubicon yeah can i tell you one more therapist yes please that i wrote in my book. And I'm sure my ex-boyfriend would like, my ex-boyfriend and I, his name was Michael. We really tried. We went to a lot of couples therapy. We really, really tried. And we went to the couples therapist. He was talking to the therapist and he said, Andrew sucks the air out of every room we go into. It's like, I'm not even there. Every time we walk into a room, it's like, no one even sees me. And he went on and on and on. And then the therapist said, Andrew, did you hear what Brian just said? And I said, his name is Michael.

He went, what? And I said, his name is Michael. The same thing happened to me. I talked about this on an earlier episode. My therapist was like, oh, your boyfriend, Greg? I'm like, you mean my husband, Brad? I love it. I love it. Not great. It's not I love it. Not great. It's not great, Chelsea. Not great. I'm going to bring up my favorite story in the book, which, of course, is you having sex with a married man and then having his wife return your panties to you.

Oh, no. Yeah. Oh, yeah. We actually read it. Oh, yes. Yeah, we read it together. You actually read the book. Yeah, yeah, yeah. I'm a reader and Catherine is a podcast producer, we read it together. You actually read the book. Yeah, yeah, yeah.

I'm a reader and Catherine is a podcast producer, like she said earlier. So that's our job to read your book. I know, but I didn't think most people actually read it. Oh, I forced your team to send it to us. Oh, God. Okay. I did have sex with a very ultra conservative married man, just like a one night stand. And it was a strange situation. And I regret doing it. I wonder how he's doing now is sort of my, because I've not kept in touch.

Well, and then the part about his wife returning your underwear to you. Yeah. What was that like when you started getting texts from her being like, I want to talk to you? Oh, that was a little tricky. So I left. He sort of took all of my clothing with him and we were doing a musical together. And a couple of days later,

she showed up in town and she did arrive with my washed and cleaned underwear in like a little baggie. Like a sachet? Well, it was like a little FedEx bag. And was totally fine with the fact that he was gallivanting around with men, correct? I mean, I don't know if she was fine with it, but I think that she had come to terms with it. I think she had made up her mind that like, we're going to get through this. Well, if you think about the dynamic between a gay man and a woman, right? Like your bestie, whoever your best friend is, that's a gay man. Ideally,

the best chemistry would be for the two of you to be married and just let her fuck men on the side. You're in a long-term relationship. I know you two are a very hot couple, you and your boyfriend Tux, your partner, I should say. Well, thank you. Because you're more than boyfriend and boyfriend, right? Well, yeah, boyfriends, partners, yeah. We're not married. We met doing Boys in the Band together, 2018.

And we've like, you know, it's like the laziest story ever that like two actors met doing like a show together. Couldn't have been lazier. I have to say, I told Chelsea this morning, I was like, when I realized that's who Andrew Reynolds was dating, it was like the two of you together are so incredibly hot as a couple. I was taken aback. You also sort of kind of look alike, similar.

So I'm sure you've heard that before. You do have a similar vibe. Yeah, you look like you're both from a different decade, but a very similar. Is that narcissistic that I'm sort of dating myself? Probably. I mean, what else could it be? I know. Dumb actor. Dumb actor. Yeah. No. And people have asked me like, well, how did you guys meet? I was like, well, we were playing boyfriends in a movie. And that's as simple as it is. But aren't you like a stepfather? You know, I try my best to sort of be as present as possible. I'm not there a lot, unfortunately. I work a lot in New York. And he's in L.A.? And he's in Los Angeles. Yeah. And I...

I can just pop over there and look after the kids. I love children. So you just tell me when. I know. I can take some of the load off. I know you dig a kid. I know that from just being a fan. But, you know, it's like it's tough because I'm gone a lot. I try to be as present as possible. I really do.

I really liked in the book how you talked about sometimes having a difficult time connecting with them. Chelsea and I have talked about this, too. It's, because they're like preteen-ish, right? They're like 11-ish? They're 10. Okay. But it's like, sometimes you're like, what do I talk about with a 10-year-old? It can be difficult. Yeah. But you know, I hate fucking having to make conversation. I fucking hate that. So when you're talking to a 10-year-old, like that isn't related to you, even when they't related to you even when they are related to you sometimes it's like it can be a chore like that's why people become parents because they're ready to take that responsibility on and I think what I find so annoying is that

I'm not supposed to take that on I chose not to do that so don't expect me to mingle like with your kids unless they're fucking cool and then I'm into your kids like I'm into really cool kids my friend Jamie Greenberg has a really cool kid. Yeah. Lenny and I like her. Yeah, but kids are mostly not cool. Yeah, they're idiots because they haven't grown up yet.

And I think being a parent and I really appreciate my siblings skill at this that they really do engage with their kids in a great way. And I found that i maybe don't have that skill like i don't i don't have that like natural thing where i'm like oh i know how to talk to a kid i don't always know how to sometimes i can like sort of drop in and be, and there are moments with Tuck's kids where like, I do it well, but like sometimes I don't do it well.

And it's really hard to, it was a really hard lesson to learn that, oh, you're not naturally good at this. And some people are naturally good at it. Some people just like know how to do it and know how to talk and like fuck around with kids but like i don't have that gene and it was a really hard lesson to figure out oh you don't know how to do it that was tricky i'm good with like the fun stuff i'm good at like messing around at a Target. Right. Doing some voices and having some fun.

I'm good at that. Taking them to school, not so good at. Not so good at. Making breakfast, not so good at. What do you think that you're really good at? Not with regard to parenting, but in life in general, like what do you think one of your greatest gifts is? I feel like I'm a pretty good friend.

Like I keep in touch well. Okay, I think. Now you're going to get some responses from my friends. They're going to be like, no, he doesn't. No, he doesn't. I don't need a lot of things or people to be on top of me. Well, I don't feel like I do either. And I feel like sometimes that bites me in the ass a little bit that like, because I don't feel like I do either. And I feel like sometimes that fights me in the

ass a little bit that like, because I don't need a lot, then sometimes I don't maybe necessarily give. Yes. I think those two things are twins. Yes. I think if you do one, you do the other. Exactly. Yeah. I'm guilty of the same thing. Yeah. I don't need a ton from you. So then maybe if I don't always give it back, then I'm looked at as sort of being selfish or being, I don't know. That's a thing that I just sort of realized about myself. Yeah. But selfish is a judgment. So like, you shouldn't think about it that way. You should think about like, are you taking good care of yourself or are you actually like ignoring the needs of other people that are important to you?

That kind of thing. Well, that's a nice way to say it. Well, I learned that in therapy. I'm going to give you, I'm going to just send you like a Venmo because I feel like this has been like a real therapy session. Well, that's great

because you're about to give therapy to our callers. We have people live that call in. I'm very excited about that. So get ready. Catherine is going to get us up to speed. Hold on. No, you don't get any prep time. You don't get any prep time, Andrew. Is there anything that I should know? Like, is there anything I should be prepared for? Well, there's a couple of sex questions, but we're going to take a quick break and we will be back with colors and questions. 2025 is bound to be a fascinating year.

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We got the answer. Will space junk block your cell signal? The astronaut who almost drowned during a spacewalk gives us the answer. We talk with the scientist who figured out if your dog truly loves you and the one bringing back the woolly mammoth. Plus, does Tom Cruise really do his own stunts? His stuntman reveals the answer. And you never know who's going to drop by.

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And we're back. Oh, my gosh. And we're back. We are back. Let's start with a breakup question. Oh, boy. Are you ready, Andrew? Are you ready?

My gosh. Yes. This might be a quickie, but we'll see what comes out of it. This comes from T in New Zealand. Dear Chelsea, I need to break up with my boyfriend. We met last summer when we started a new job together. Things moved super quickly. We've been dating for about seven months now, but it's just not working out.

He's still a great person, and I care about him. I'm a 28-year-old male, and he is 24. Now, my dilemma is this. Our work schedules are totally opposite. The days I'm not working are the days he is working, and it's just how our fixed schedules happen to work out. Not only that, but we live 85 kilometers, which is about 50 miles, apart from each other. Thank you for that conversion. You're welcome. Yeah, thank you. Thank you for doing that. I was trying to do the math in my head. I can't do it. No, it's impossible. Even Siri couldn't do it. I had to like find a calculator. We live 50 miles apart from each

other and work somewhere in the middle. We don't see each other often, and I've been trying to schedule a time to hang out, but it's proven unsuccessful. He wants to hang out on Wednesday when I'm finished with work, but I feel bad he'd drive all that way just for me to end things and then he'd have to drive back. However, I know ending things over the phone is like the cliche movie scumbag move. Do you think it's acceptable in this situation? If you were in his shoes, would you hate the person who broke up with you over the phone more than the person who made you drive 170 kilometers. Thank you, T. I think that's a phone call then.

If he's going to be driving. Yeah, that's just the right thing to do. Like, I can't. You can't make somebody drive to you to get broken up with. Right. That's so fucking stupid. First of all, that entire conversation is stupid. They're in their 20s.

They're not really dating. They don't live in the same city. Fuck off. You're not in a relationship. You don't live in the same city. You're in your early 20s. You're not dating each other. It's not a big deal.

Just say it over the phone. Do not drag that out. That is so obnoxious. Agreed. No text, but a phone call. Yes. I know. I'm sure they have really cute accents, but like done. I'm done. Yeah. I'm done with that one. Got to nip it in the bud. Next caller. Well, our next caller is Devin. Devin says, come a long way since our breakup and have embraced my slutty phase by sleeping with dozens and dozens of men and exploring other kinks that I didn't have a chance to explore before. My problem is this. Even after a year and a half of being separated, I still feel insecure about seeing my ex in public or running into him at a party. Portland is a small gay community, and I often

see him at our local gym. I can't help myself but think about the guys he's sleeping with or the men he might casually be dating. To add insult to injury, I was primarily the bottom in our relationship and he rarely let me top. I told him time and time again that I wanted to top, but somehow we always found ourselves in the same positions. After our breakup, I was still logged into his Amazon account when I found a douche used to clean your butthole before sex, and I really got in my head about him bottoming for other guys when he wouldn't do that in our relationship. We struggled a lot with insecurities on both sides, and both suspected the other wanted to sleep with guys with bigger dicks. Do these feelings come up in heterosexual relationships as well? I've tried to refocus and channel my thoughts other places when these things come up, but sometimes I can't help but fixate on them. Any advice you have is much appreciated. Much love, Devin. And Devin is here with us on the phone. Oh, Devin's here. You can counsel him directly, Andrew. I can't wait for this.

Devin, the bottoming conversation, it really took a turn. Devin. I did not, I was not following. Hold on. Devin's muted first of all. Just hold your role. Andrew, slow your roll. Okay. Devin, do you see Andrew? Here's our special guest. How lucky are you? Hi. Hello. Devin, have you since found a top that satisfies your needs? I'm still dating. I actually had a date last night just sort of like casually dating and kind of checking things out all right so the answer the short answer is no i just i'm

kind of like still doing my thing sleeping around doing what i can and what's the portland scene like is that a big gay scene it's relatively big i would say but it's a lot of the same people the pool is still kind of limited it seems like and a lot of what, but it's a lot of the same people. The pool is still kind of limited, it seems like. And a lot of what I've encountered is a lot of people are in open relationships also. I know. That's such a weird headache, right? People who are in open relationships and you're like, do it or don't. Come on now. How long have you guys been broken up, you and your ex-boyfriend? About a year and a half. So Halloween of 21. So quite a while.

What did you dress up as on Halloween? Is that really necessary? Chelsea, I think it's an important question in this conversation. It's important. The last few years I've dressed up as Trixie Mattel. Okay. So that, Chelsea, I feel like that's very informative. Okay.

I feel like we needed to hear that. Okay. Well, and then how does that change and pivot your thinking, Andrew? Well, I feel like you're a power bottom. Uh-huh. Okay. So you're definitely a power bottom. I think that it's a long time for you to be still obsessing about your ex.

So have you been to therapy? I have, yes. But it's been quite a while just because I was seeing a woman therapist and her and I really hit it off. But then she recommended I start seeing a gay therapist because I was teaching her more than I was, I guess, getting back. So she recommended I see a gay therapist. She sounds like a bottom. Yeah. And the two guys that I saw, I didn't connect with them enough.

I felt like I was venting more than I was receiving, I guess. How are you meeting people in Portland? Are you like on apps or is it just sort of more of a general, you're just hanging out in bars and things? A little bit of both, like Grindr, but that's a lot of just like hookup culture. You know what I mean? Yeah. Whereas like, so I went on a date last night, in fact, and I saw him on Instagram. And that's kind of been a way and I kind of reached out and just kind of went out on a limb like, Hey, I think you're really handsome. Kind of put myself out there. I said, I know this is a little forward, but like, I think you're really handsome. You seem like a cool guy. Can I take you out? So we went out for a drink. So how'd that go? It was really positive. Yeah, it was really,

yeah, good. It was a good experience. Yeah. Well, that's good. Yeah, I think you have like a lot going on. I think you're like allowing yourself to fixate, which is just kind of like a mental game that you're playing with yourself. And I think, you know, talk therapy is a good way to like deal with that. Because you shouldn't have to be obsessing about like, it's none of your business what he's doing with other people. He's not your boyfriend anymore. It really doesn't matter. You're going to have like a succession of men in your life moving forward. And regardless of Portland being a small town, so what? So like the sooner you warm up to the idea of bumping into him and not being so injured by it, I think the sooner that it will become normalized and the sooner you can move on from

this kind of tethering you have to him. That's a very good way to say that, Chelsea. It's like, he's not your ex-boyfriend. He's just a man. Just another person. Yeah. And you should actually try to bump into him so that the quicker that that happens and the sooner you get the ball rolling of normalizing it, even though it might feel gross right now or like you're not ready, I think you should kind of just force yourself. It's been enough time. And just force yourself to be around him when, you know, you see him be cool. Hey, it's nice to see you. Don't bring anything else other than just complete, like, just be cool. So that way you can leave that situation. He knows. And then you kind of diminish the tension between you two. Yeah. And I think I run into him primarily at the gym and like he'll ask me to

walk the dog or watch her if he's out of town and there's part of it like that i don't love it either because i don't like to be in his space like i don't like going into his apartment i don't mind running into him at the gym sure but yeah it's like i don't really want to be in a space i don't want to and i think part of it's like i identify that i'm still a little injured by some of these things and like it's all feels very surface level. What we end up talking about, it's all like BS. Hey, how's it going? Just stupid stuff. I feel like there's part of me that I still want to talk about some things that I'm injured by and some unresolved feelings, I guess. But I don't know. I just need to like, let that go and move on. And yeah, maybe you just let that go.

I think it's a practice of letting things go. It's doesn't, it's not the easiest thing because you can hold grudges against people and lay blame because as long as you're doing that, you're kind of the victim. And I think there's a little bit of victim and victiminess in there. You know what I'm saying? I think you should really, really try to practice letting go of any anger you have towards him. Relationships don't work out all the time. It's really nobody's fault. You know what I mean? It's just a matter of chemistry and longevity. So like, don't hold, I mean, I know you do, and I know we all do, but it's something that you want to start thinking about and actually start practicing, like whether it's a mantra, whether it's a meditation,

whether it's you reminding yourself every morning, like you want to give out love, not resentment, you know, as long as you're holding holding onto that, it'll kind of have a negative effect on you. Sure. Okay. I mean, that's something that I could use as well. So thank you. He's getting a double dose. We're giving therapy to you and we're giving advice to you and to Andrew. Yeah. Yeah. Thank you. You've also given it to me. Devin. So like now when you're like looking to date people, are you looking for the opposite sort of person? Or are you looking for someone who's sort of similar? Like I've not been on the dating apps, but when you're scrolling through, are you looking through sort of a similar situation or do you feel like you've passed that? Are you hitting on him right now? Are you, Andrew,

are you hitting on the car? No, I have a boyfriend, Chelsea. Oh, oh, I'm sorry, Devin. Are you looking for someone that's based in New York and loves to sing? Whoopsie doodle. Anyway, Devin, are you good with that advice? Can you start doing that? Can you, do you understand what I'm saying when I say start practicing it? Like, does that register? Yeah. Just sort of like, let go, kind of forget about it. Move on. Just kind of like, let the, like, kind of like give up the resentment. Yeah. Look at him with love. Like whenever I don't like someone, I'm always have to, I say, I'm like, love, just love people. Who cares? You don't have to hang out with that person, but just show them kindness and love. It's just good vibes to be given out anyway. You know what I mean? Sure.

And I think kind of what right now, what's kind of happening is we get into these little fights or spats. And so then I like leave kind of like resentful and I'm like upset. And then I just like, where do you get in fights and spats? Well, he's watching his dog. Yeah.

Like, no, no, no, no, no, no more watching the dog. That's no,

that's a wrap on that. Like Andrew said, he doesn't like that. I don't like that either. Yeah. Okay. And the dog. That's a wrap on that. Like Andrew said, he doesn't like that. I don't like that either. Yeah. And you don't need to be like his friend. You don't need to be there to support him. Especially you shouldn't be arguing with your ex-boyfriend.

There's nothing to argue about. You're not together. But that makes sense why you're still hung up a year and a half later since there's been this sort of constant contact. You are postponing this situation for yourself. So you have to stop going over there and taking care of his dog. And you certainly have to stop arguing with him. There's no more arguing. You just won't participate in it. Okay. Yeah. Yeah. Okay. You can do this. I can do it. Yeah. Go get him, Tiger. Okay. Bye, Devin. Thanks for calling. All right. Yeah. Thank you, guys. Thanks, Devin. Some people need a very firm hand. Devin was a real sweetheart. He was,

and he needed a swift kick in the ass because he's like, he did. He cannot watch that man's dog going over and then fighting with that. Fuck off. You're lucky I'm fucking babysitting your dog. I would never babysit anyone's dog. I once babysat this couple's, I worked with this girl at this restaurant once and she asked me to babysit her dogs and stay at her house, which she thought was fun for me. It wasn't. And so I decided after two nights, I'm like, I can't stay here anymore. So I just wanted to stay at my own place. Or I had a boyfriend or something.

And so then I would just leave the dogs there and go and feed them in the daytime and take them for maybe a walk. And I did that the whole week. I was like the worst dog sitter in the world. But they were fine, right? Yeah, they were, but I wasn't dog sitting them. I was feeding them. Well, that's, one can argue that's more important. Should we hop to our next caller?

Yes, let's go to our next caller. We have another caller. I'm very excited. Okay. Look alive. What do we got? What do we got? Ramon.

Ramon writes, Hey, Chelsea, I'm having a serious problem. My last three long-term relationships have begun well, or so I thought. They turned into toxic relationships that involved addiction, me being subjected to emotional abuse, manipulation, and sometimes violence. I ignored quite a few red flags at the beginning of these relationships because I was raised to give people the benefit of the doubt. I would also try to ignore the bad and focus on the good, hoping they would change, and they never did. My question is how do I avoid ending up in yet another relationship with a toxic or narcissistic manipulator without sacrificing my belief that people can change and deserve second chances? I'm taking some steps already, like listening to my intuition,

being careful with ignoring red flags as they appear, and just generally trying to protect my energy and not give it so freely. I appreciate any help and insights, Ramon. Hi, Ramon. Hi. Ramon, that was a very thorough description of your relationships. Thank you for sharing that. Well, thank you. Yeah, it's been three in a row of verbal and physical abuse, addiction,

and then realizing my most recent relationship was a narcissist on top of all that as well. Oh boy. How long did the relationships last? So my first with my ex-husband was 10 years. Oh, wow. Yeah. And then the third one was about five. And this most recent was three. So it's almost been 20 years. That's a long time.

Yeah. Chelsea, what are you? I mean, I'm sure that you had a lot of childhood trauma. Have you? Yeah. So I was kind of raised to give people second chances. And that's part of why I wrote in was I don't want to give that up. And I want to see people for who they are.

But, you know, I did. My dad used to be my mom and, you know, I grew up as an only child. So I guess there's a lot of I can relate to people and that this is good enough for you and that's not good enough for you. And what you're in charge of is changing the narrative of your own story. You're the only person in the world that can say, this is beneath me. I am no longer settling for this. No one else can do that for you. So until you're ready to make that decision and that declaration to yourself and to the entire world, then you're going to keep bringing these people into your life. You have the ability to stop this.

It does not have power over you. It does not. Yeah, with the most recent relationship, I did end it. He's still harassing me here or there, but for the most part, I'm away from it. And I'm being more protective of my energy, who I give it to, who's around me, and just trying to be observant that I don't, again, court that same energy to me.

And listening to podcasts like this and some other resources I've been using is kind of getting me to that headspace where I can maybe be a little more defensive without giving up my belief that we should take people as they are. But you don't have to think of it as a negative. Those two things aren't mutually exclusive is what I'm trying to say. You can hold all of that in a very positive light. It's not like you're rejecting people. You're protecting yourself. You don't have to think of it as a rejection or as a defense mechanism. It's a self-preservation, a self-protection, something that you haven't been practicing your entire life

because of something that you had no control over that happened to you as a child. But the difference here is you're an adult now. You have all the control and you're choosing to still set up situations that are emblematic of your childhood. So it's so much simpler than you even think it is. And it's so much easier for somebody like an outsider to point it out to you. Right. So I just want you to have clarity about how easy this can be once you like really make the decision that you're done. And it sounds like you already have. Yeah. You know, like I said, that relationship's over. I still feel for these people, you know, and I wish them ill. I want them to be the most successful people on the planet just over there, away from me. And, you know, when I left this person, I said, look, I got to look out for me.

I got to protect myself because I was getting to a really kind of dangerous space. Like it was just very stressful. I was constantly like fight or flight. I couldn't sleep because I'm like, is it going to come in to the bedroom and cause a scene or do something drastic? So but now I'm in my own place, my own space, and just trying to focus, as you said, on protecting myself. But just, you know, I don't want to lose that empathy for other people. You're not going to lose that. You don't lose that stuff.

That stuff is ingrained in you. You know, you either have empathy and you don't. I mean, you can gain empathy if you don't have it. You can practice it. I've done that. But you don't lose what you have. Like, that's a natural gift. Most people have it.

Some don't. But, you know, that's a separate conversation. But I believe in you. I believe that you can totally make these changes. I know you can because you're thinking about it. And you don't have to be worried about these kinds of people coming into your life. You know how to recognize it right away. You have a huge advantage. And it's not a rejection. It's a protection. Just put a positive word to every negative word you're thinking because there always is one. And it's usually the opposite.

Yeah. And you don't have to think of empathy as like this thing you're going to lose. The truth is like there are red flags, there are orange flags, there are yellow flags. So as you move forward, there are purple and blue and green. But just because you have empathy for someone doesn't mean you need to let them into your innermost being or your checking account or your life or any of those other things. Like Chelsea said, protecting your energy and recognizing like, oh, this person is showing me red flags. That means they're not a good partner for me, but like I can still be friends with them, whatever. But seeing like some yellow flags like that might be okay. It just depends on what that

is for you. But also knowing like you have a history of being okay with those red flags coming into your space. It's part of that acceptance. You know, I accept the people as they are. And I'm good at compartmentalizing things because I think I did that as a kid. Compartmentalize, oh, my dad beat my mom, but he also loves me. So how do I resolve that? So when a person's terrible to me, I'm like, well, but they're really sweet here. So I'll just put this away and I'll fix it later or we'll work on that. But yeah, now, I mean, after 18 years of this, I think I'm done. But yeah, I think that the key is I just didn't want to just be so cold and just like shut it all off, but kind of bouncing it better, not giving it away and, you know, losing that part of me. But also like you're the conductor. It's not up to other people. It's up to you. So it's easy when you're in charge to, you know, that like, OK, I'm the one who making who's making these decisions ultimately to allow these people into your lives. So it's not like, you know, you have to defer to

somebody else or you have a partner that you're who's doing this. It's you. So even easier to fix. I wonder if there is an opportunity here because you are continually attracted to these people who are horrible. You got to read that book Attached also. That talks all about these kinds of unhealthy attachments. Have you read that? I have it on my audio. Read it. Start it today, please. There might be a way to bring in some reinforcements, whether that's the friend who's been telling you for years, this guy's bad for you. He's awful for you. Get away. Bringing in a friend, bringing in a therapist to be like, OK, here's what I'm experiencing in this new relationship. Is this actually healthy? Is this something I should move toward or cut off right now or move into the friend zone right now?

Yeah, my company has some resources for therapy that I'm going to, you know, look into because it's just unacceptable. I can't do it anymore. Like, I mean, it's just been too long, you know, at my age, I don't want to have another one of these pop up. So yeah, I definitely want to focus on making that not happen again. Yeah. And they're not your responsibility, you know, these other people in the relationship. Yeah, Ramon, go get your act together. I they're not your responsibility. You know, these other these other people in the relationship. Yeah. Ramon, go get your act together. I've got faith in you. Thank you. And like I said, this podcast actually, when I was in the darkest times with this person, helped me get away from it because these conversations that you have with people and the people you have calling in, it really did help me a lot.

So thank you. I'd love to hear that. All right. Well, thanks for calling in Ramon. Bye Ramon. Thank you guys. Oh, Jesus. Ramon. Yeah. Ramon. Lots of serious stuff you guys. Serious business. We're running a medical practice here. This is serious shit. I know you're doctors. Everyone needs a self-esteem boost. Everybody. Everybody needs like an injection of self-esteem every morning. It is really true. I think we could all use that. I know.

I wish I knew what that could be. I mean, I feel like you come in the room and it's an injection of self-esteem. It's just like, Laura, like you give that to yourself in the morning because you come in the room and it's just like, here I am. I'm present. I don't know. It's big energy in a good way. Thank you. I appreciate that. You are good energy. Andrew, I think let's take a quick break. Let's do a quickie. Oh, my God. You always interrupt the breaks, Andrew. God, they're so long.

OK, we're going to take a quick break. Andrew's not going to say anything, and then we'll be right back. 2025 is bound to be a fascinating year. It's going to be filled with money challenges and opportunities. I'm Joel. Oh, and I am Matt. And we're the hosts of How To Money. We want to be with you every step of the way in your financial journey this year, offering the information and insights you need to thrive financially. Yeah, whether you find yourself up to your eyeballs in student loan

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And I'm Peter Tilden. And together on the Really No Really podcast, our mission is to get the true answers to life's baffling questions like why they refuse to make the bathroom door go all the way to the floor. We got the answer. Will space junk block your cell signal? The astronaut who almost drowned during a spacewalk gives us the answer. We talk with the scientist who figured out if your dog truly loves you and the one bringing back the woolly mammoth. Plus tom cruise really do his own stunts his stuntman reveals the answer and you never know who's going to drop by mr brian cranson is with us how are you hello my friend wayne knight about

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And register to win $500, a guest spot on our podcast, or a limited edition signed Jason bobblehead. It's called Really, No Really, and you can find it on the iHeartRadio app, on Apple Podcasts, or wherever you get your podcasts. Hi, I'm Dani Shapiro, host of the hit podcast, Family Secrets. How would you feel if when you met your biological father for the first time, he didn't even say hello? And how would you feel if your doctor advised you to keep your life-altering medical procedure a secret from everyone? And what if your past itself was a secret and the time had suddenly come to share that past with your child? These are just a few of the powerful and profound

questions we'll be asking on our 11th season of Family Secrets. Some of you have been with us since season one and others are just tuning in. Whatever the case and wherever you are, And we're back. We are back. on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. And we're back! We are back. This one should be an easy one for Andrew. I'm back! I'm back! He's back. Dear Chelsea, I'm 41 and my boyfriend is 26. We met almost two years ago, and he was super inexperienced sexually. When we met, we agreed we'd have an open relationship, but so far we've been monogamous. Our sex is very regular, but incredibly vanilla. I've tried to spice it up, but it's been met with very little enthusiasm.

I feel like he needs to experience more dick. A variety of dick. The thing is, I get anxiety when I think about opening him up to others, but I really think it's time to bring this up. What's your advice for... You need to go out and get some dick. What's your advice for getting myself comfortable and accepting that this young guy deserves my permission for more penetration? Robert.

Andrew? Robert. Robert, no. No? He's 41 and his boyfriend is 26? Yes. And they've been together since his boyfriend was 24. No. No. He's 41 and his boyfriend is 26. Yes. And they've been together since his boyfriend was 24. No.

No. Let him go. Set him free. Like totally go. Yeah. Or open. Who cares? Just let.

Yeah. He let him. I mean, you can't force him to go get dick. No. But you can make the suggestion. Yes. No. Let him go, Robert. Let him go. Everyone needs to sow their oats. I really am make the suggestion. Yes. No, let him go, Robert.

Let him go. Everyone needs to sow their oats. I really am a firm believer of that. I mean, how do you know what you like unless you try tons of different things? Yes, you do a bunch of different stuff and then figure it out. No, Robert, let him go. How old were you when you lost your virginity, Andrew? I was 16.

Are you gold star? What does that mean? I'm gold star. That means never had sex with a woman. Gold star, but not platinum. Oh, wait, what's platinum? Born via C-section. So never touched a vagina.

Never touched a vagina. Got it. That's good i'm just i'm just platinum wow okay fantastic what's better than the platinum anything no i mean i don't know there was father if your mother was a father and you never were even inside a woman's body well no that doesn't make sense because you have have to. Well, no, I have to think that one through. Workshop it, workshop it. I will. I'll continue to workshop it.

I'm sure it won't offend anybody, me questioning. Right. Well, we're ready to wrap it up, Andrew. I'm going to encourage everybody to get your book. Well, thank you so much. And I can't thank you enough for having me. Again, huge, huge fan. First time caller, but longtime listener.

And man, oh man, am I a fan of yours. And I'm so happy to meet you. Thanks, honey. It's so nice to meet you. We could end with that. Should I sing something? Of course.

Wait, make sure you guys all get a copy of Uncle of the Year. That's his second book. Andrew's second book. Congratulations on the publication. It's very funny. Everybody grab a copy and read it. You're going to love it. Thank you. No problem. Have a great day. Thank you. Bye. Bye. And I have just announced new stand updates for my Little Big Bitch Tour, guys. I announced 25 new cities. These are probably a

lot of the cities people have been mentioning in the comments. I start out in East Hampton. I go to New York, D.C., Durham, North Carolina, L.A., Phoenix, Cleveland, Columbus, Pittsburgh, Milwaukee, Chicago, Madison, Portland, to name just some. I will be performing at the Kennedy Center, everybody. That's in D.C., October 6th. I'm super psyched to be performing there. Also, I just added second shows in New York, D.C., Seattle, and San Francisco. There are more. I have dates coming up for the next three months and then more dates coming up in the fall. So those have all been announced. They're on my Instagram page or you can go to ChelseaHummer.com. Thank you. If you'd like advice from Chelsea, shoot us an email at DearChelseaPodcast at gmail.com

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Every week, I talk to brilliant minds and brave souls about the art of small, powerful choices. Our listeners say it all. This is a lifeline. Transformational. The best antidote to a bad mood I've ever heard. Join the pack and start feeding your best self. Listen to The One You Feed on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

Joel, the holidays are a blast, but the financial hangover, that can be a huge bummer. If you are out there and you're dreading the new statement email that reveals the massive balance that you may have racked up, well, you could use our help. That's right. I'm Joel. And I am Matt. And we're from the How To Money podcast. Our show is all about helping you make sense of your personal finances so you can ditch your pesky credit card debt once and for all, make real progress on other crucial financial goals that you've got, and just feel more in control of your money in general. You know it. For money advice without the judgment and jargon, listen to How to Money on the iHeartRadio app, Apple Podcasts,

or wherever you get your podcasts. I'm Jason Alexander. And I'm Peter Tilden. And together, our mission on the Really Know Really podcast is to get the true answers to life's baffling questions like why the bathroom door doesn't go all the way to the floor, what's in the museum of failure, and does your dog truly love you? We have the answer. Go to reallyknowreally.com and register to win $500, a guest spot on our podcast,

or a limited edition signed Jason bobblehead. The Really Know Really podcast. Follow us on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. People, my people, what's up? This is Questlove. Man, I cannot believe we're already wrapping up another season of Questlove Supreme. Man, we've got some amazing guests lined up to close out the season,

but, you know, I don't want any of you guys to miss all the incredible conversations we've had so far. I mean, we talked to A. Marie, Johnny Marr, E, Jonathan Schechter, Billy Porter,

and so many more. Look, if you haven't heard these episodes yet, hey, now's your chance. You gotta check them out. Listen to Questlove Supreme on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.