Minisode: Gayest Cities with Chelsea + Catherine

Summary

Podcast Summary: Dear Chelsea – Minisode: Gayest Cities with Chelsea + Catherine

Episode Information

• Title: Minisode: Gayest Cities with Chelsea + Catherine
• Host: Chelsea Handler
• Co-Host: Catherine Law
• Release Date: March 7, 2025
• Description: In this Minisode, Chelsea Handler and co-host Catherine Law delve into what makes a city gay-friendly, offering insights and recommendations for listeners considering relocation. Alongside answering listener questions, they share personal anecdotes and engage in lively discussions about the best cities for the LGBTQ+ community.

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1. Opening and Listener Email: Embracing Menopause (00:58 – 02:58)

Chelsea and Catherine kick off the Minisode by addressing a heartfelt email from a listener named Maggie. Maggie shares her positive outlook on menopause, describing it as a "complete liberation" and a "gift." She highlights the societal misconceptions perpetuated by the pharmaceutical industry and celebrates the newfound freedom it brings.

Maggie (via Catherine) [01:56]: "Menopause is something to look forward to. Oh, all caps. It is a gift. It's complete liberation from everything the patriarchy wants us to think it's bad because we stop giving a shit about men once it starts."

Chelsea and Catherine express their admiration for Maggie's perspective, reinforcing the Minisode’s commitment to tackling diverse and personal topics with honesty and humor.

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2. Listener Call: Couples Counseling and Relocation Dilemma (03:00 – 10:46)

The primary focus of this Minisode revolves around a listener couple, Kendall and Olivia, seeking advice on choosing a third state to relocate to. Currently residing in Massachusetts and New Hampshire, they are grappling with the challenges of long-distance and seeking a new home that caters to their relationship and lifestyle.

Discussion Highlights:

• Exploring Connecticut (03:49 – 04:18):

  Chelsea suggests Connecticut as a balanced choice between Massachusetts and New Hampshire, appreciating its vibrant cities and picturesque landscapes.

  Chelsea [04:02]: "I think Connecticut is a nice compromise between the two, and it still has the same vibe that you're used to."

• Portland, Maine (04:22 – 05:35):

  Catherine and Chelsea commend Portland for its charm and LGBTQ+ friendliness, recommending it as an ideal destination for the couple.

  Chelsea [04:24]: "Portland, Maine is awesome. I find that just to be just a cool, cool town all the way through as it's like a mini city... there's a lot of like minded people there."

• Vermont and Skiing Options (08:03 – 09:00):

  The conversation shifts to outdoor activities, with suggestions of Vermont for its skiing opportunities, even though Olivia admits she has never skied before.

  Olivia [08:14]: "Always been a big skier, but I've never skied in my life. Chelsea, believe it or not. But we want to get into snowboarding, actually."

• Chicago’s Andersonville and Portland, Oregon (09:19 – 10:04):

  Catherine highlights Chicago's Andersonville as a vibrant area for lesbians, while Chelsea recommends Portland, Oregon for its creative and outdoor-friendly environment.

  Catherine [09:34]: "Chicago is an amazing city to be young and gay in... you can head up to Andersonville, which is like, a lot of cities have like a boys town, but that's where all the lesbians live."

• Practical Recommendations (10:04 – 10:30):

  Both hosts advise Kendall and Olivia to spend weekends exploring potential cities, emphasizing the importance of experiencing the local vibe, cuisine, and cultural activities before making a decision.

  Chelsea [10:04]: "Do a three day weekend in a bunch of different cities. Get an Airbnb, walk around and make sure you incorporate all the things you love."

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3. Key Insights and Recommendations

Throughout the Minisode, Chelsea and Catherine provide valuable insights into what makes a city gay-friendly, focusing on factors such as community presence, cultural activities, affordability, and lifestyle compatibility.

• Community and Culture: Cities like Portland, Maine, and Chicago’s Andersonville are praised for their strong LGBTQ+ communities and vibrant cultural scenes.

• Outdoor Activities: For those who love the outdoors, Vermont and Portland, Oregon offer ample opportunities for skiing, snowboarding, and other outdoor pursuits.

• Balancing Lifestyle Needs: Connecticut is recommended as a middle ground for those accustomed to the East Coast vibe but seeking new experiences without straying too far from familiar surroundings.

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4. Notable Quotes

• Maggie on Menopause (01:56):

  "Menopause is something to look forward to... It is complete liberation from everything the patriarchy wants us to think it's bad."

• Chelsea on Portland, Maine (04:24):

  "Portland, Maine is awesome... there's a lot of like minded people there."

• Catherine on Chicago’s Andersonville (09:34):

  "Chicago is an amazing city to be young and gay in... Andersonville, which is like, a lot of cities have like a boys town, but that's where all the lesbians live."

• Chelsea’s Advice on Exploring Cities (10:04):

  "Do a three day weekend in a bunch of different cities. Get an Airbnb, walk around and make sure you incorporate all the things you love."

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5. Conclusion

In this Minisode of Dear Chelsea, Chelsea Handler and Catherine Law adeptly blend humor with heartfelt advice, addressing both personal health topics and significant life decisions like relocation for a thriving relationship. Their thoughtful recommendations and authentic engagement with listeners' concerns exemplify the show's commitment to being both entertaining and deeply informative.

Listeners contemplating a move, especially within the LGBTQ+ community, will find Chelsea and Catherine’s insights invaluable as they navigate the complexities of choosing a city that aligns with their personal and relational aspirations.

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Note: This summary excludes advertisements and non-content sections, focusing solely on the meaningful discussions and advice provided by Chelsea Handler and Catherine Law.

Transcript

[Chelsea Handler]

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[Chelsea Handler]

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[Catherine]

Morning brings a fresh new energy. And no matter what the day holds, we come to the Today show for all of it.

[Savannah Guthrie]

We get the best start to the.

[Chelsea Handler]

Day because we started together.

[Craig Melvin]

Watch the Today show weekdays at 7am on NBC.

[Chelsea Handler]

Hi. Hi Catherine.

[Catherine]

Hi Chelsea.

[Chelsea Handler]

Welcome to our mini mini mini Minisodes.

[Catherine]

Just like a teeny weeny soda. Chelsea, I have a fun email from someone that totally relates to our Naomi Watts episode that just came out. Maggie says I can totally second that. Menopause is not all terrible. It's not all doom and gloom. I'm 58 and postmenopausal and I'm here to tell you that menopause is something to look forward to. Oh, all caps. It is a gift. It's complete liberation from everything the patriarchy wants us to think it's bad because we stop giving a shit about men once it starts. The pharmaceutical industry wants us to think it's bad because they can sell us meds for it, but it's awesome. To quote Kristen Scott Thomas in Fleabag, I lead a very healthy life and menopause is magnificent. So that's an exciting thing to look forward to. She also says, I have two vacation properties, Joshua Tree and Palm Springs. And I save all my Dear Chelsea episodes for when I'm driving to my properties.

[Chelsea Handler]

Oh, I love that.

[Catherine]

As soon as I get in the car, I tell Siri to play Dear Chelsea, and you and your guests are my company as I drive. Love it, Maggie.

[Chelsea Handler]

Oh, that makes me happy. I love that.

[Catherine]

Yeah.

[Chelsea Handler]

Menopause Maggie.

[Catherine]

Yep. Menopause, Maggie. Chelsea. We have two callers today for couples counseling. They are Kendall and Olivia. They are calling in from the east coast and they say, dear Chelsea, this is Kendall writing in. My girlfriend and I are both 24 years old. We met at UNH and have been together for two and a half years. I live in Mass and she lives in New Hampshire. And we can't decide on a third state to move to. I don't want to move back to New Hampshire as I went to school there, and we don't want to stay in Mass as we've been doing long distance back and forth from both states. Any help on how to decide on a third state to move to or any states you love being in? Love you both so much. Thanks for any help, Kendall. So we'll wait for Olivia before we respond, but I have thoughts.

[Chelsea Handler]

I do, too. Yeah, right off the top of my head.

[Catherine]

Yes.

[Chelsea Handler]

Well, we can get started. We'll just wait for her to pop in and then we'll recap. What about Connecticut?

[Olivia]

That's a good one. I have been there a couple times before.

[Chelsea Handler]

I mean, if you're already on the East. Do you like the east coast? Like that Eastern seaboard?

[Olivia]

Yeah, yeah, yeah.

[Chelsea Handler]

I like that part of the country, too. That's kind of my. That's where I'm from. I'm from New Jersey, so it's not quite, but I grew up on the Cape, so I like that vibe. I like New Hampshire. I like Massachusetts. I think Connecticut is a nice compromise between the two, and it still has the same vibe that you're used to.

[Olivia]

Yeah, yeah, yeah, definitely. We've also gone to Portland, Maine a couple times.

[Chelsea Handler]

Oh, yeah. Portland, Maine is awesome.

[Catherine]

It's, like, so fun and quaint, but.

[Chelsea Handler]

There'S like, tons of stuff, especially for Lesbians.

[Catherine]

Yes.

[Olivia]

Right?

[Chelsea Handler]

Yeah. What don't you like about. Hi. Hi. We were just talking about, we were just talking about your future and whether or not you're gonna move to Connecticut or Maine.

[Olivia]

Sounds good.

[Chelsea Handler]

Yeah, those two we've been talking about a little bit. So Portland, Maine. Whenever I perform, whenever I go to Portland, Maine, I always want an extra day there because I just love that food and I love Portland. I find that just to be just a cool, cool town all the way through as it's like a, like a mini city, you know, it's totally manageable and there's a lot of like minded people there. You can pack up your lesbian Birkenstocks and just go up there together and hit it. Hit it. Connecticut, I was mentioning. But Connecticut has certain parts that are really beautiful and certain parts that are a bit more rough. And I'm thinking, like the beautiful parts are really pretty expensive. But there are like cities like Hartford and you know, there are cities in Connecticut that could be. I mean, it would be worth doing a little like trip where you guys go to like hang out in some cities in Connecticut. Go to Stanford, go to Hartford or you don't want to go to Boston. Right. Because you're from Mass.

[Olivia]

Yeah. And we're, we're not big city people.

[Chelsea Handler]

Okay.

[Catherine]

Okay.

[Chelsea Handler]

So I would say go to Portland first and see what the vibe is there. If you guys like that, go for a weekend and see how you like it.

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[Chelsea Handler]

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[Catherine]

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[Craig Melvin]

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[Catherine]

And no matter what the day holds, we come to the Today show for all of it.

[Chelsea Handler]

When things are tough, we talk about it. When there's something to figure out, we dig into it. And when there's joy, we celebrate it.

[Catherine]

Because today is where it's all happening. We get the best start to every morning because we start it together.

[Craig Melvin]

Watch the Today show with Savannah Guthrie and Craig Melvin, weekdays at 7am on NBC.

[Catherine]

What kind of stuff do you guys like to do? Are you hikers? What are you doing for fun time?

[Chelsea Handler]

I feel like I'm more of, like, outdoorsy kind of stuff. I mean, but we both like doing the crafty side of things, too, like the pottery, the wine sip and paint nights, those kinds of things.

[Olivia]

And lives. Always been a big skier, but I've never skied in my life. Chelsea, believe it or not. But we want to get into snowboarding, actually.

[Chelsea Handler]

So what about Vermont?

[Olivia]

Oh, I haven't been to Vermont. Like, as an adult.

[Chelsea Handler]

Vermont's pretty cool. I don't know where. I haven't been to Vermont in so many years. I'm just trying to think of, like, what the main cities there are.

[Catherine]

Montpelier.

[Chelsea Handler]

Montpelier. But Vermont is cool. But once you're on the east coast, then you can have access to those ski places. I mean, there's Camelback, there's a bunch. There's, you know, in Connecticut, there's Stowe, there's Killington. So you can have access to all those places once you're in that area. And then there's Rhode island, there's Providence, there's Provincetown. That's super gay.

[Catherine]

Yeah.

[Chelsea Handler]

That's fun. I mean, I've been there a bunch of times, and that's a blast. And Providence, Rhode island is awesome.

[Catherine]

Yeah.

[Chelsea Handler]

I don't know what the cost of living is there. Like, if it's expensive, I probably seemingly. But I'm sure, you know, there's areas in all of these places that kind of go across the board from more affordable to less affordable.

[Catherine]

And if you do decide to venture away from the eastern seaboard, I will say Chicago is an amazing city to be young and gay in. It is a great place. You can head up to Andersonville, which is like, a lot of cities have like a boys town, but that's where all the lesbians live.

[Chelsea Handler]

Like, that's funny. Yeah, all the boys town. There are lots of lesbians in boys.

[Catherine]

Not a lot of cities have a spot for everyone.

[Chelsea Handler]

Yes, well, at least gay men are allowing gay women to take over versus straight men allowing straight women to take over.

[Catherine]

And then I would also say go to the other Portland. Like, check out Portland, Oregon. It's fantastic. There's lots of outdoorsy stuff, but also lots of creative people. But I love your idea, Chelsea, of like, go for a weekend. Like, do a three day weekend in a bunch of different cities. Get an Airbnb, walk around and make.

[Chelsea Handler]

Sure you incorporate all the things you love. You know, like, make sure you incorporate the outdoorsy aspects and like, the crafting aspects. Do your research before you go so that you can get all that stuff in. Like, make sure you go into the restaurants that you're interested in, going to, the kind of style of food you like to eat, and so that you're experiencing the city. And don't just stay in one area of that city. Really, really take in the city.

[Olivia]

Yeah, yeah, definitely. Thank you guys so much.

[Catherine]

Yeah, best of luck. And let us know where you settle. Okay. Or where you start visiting and love and that sort of thing. Okay?

[Olivia]

Yeah, definitely.

[Chelsea Handler]

And congrats on being together and being in a happy, successful relationship, girls.

[Catherine]

Thank you.

[Chelsea Handler]

Right?

[Olivia]

You don't hear that that often anymore.

[Chelsea Handler]

I know. It's nice to see, though.

[Catherine]

All right, have a great day and check back.

[Olivia]

And Chelsea, can I just back up Brittany Broski and say thank you for the interview you did with Harry Styles? Like, when she said that, I was like, oh, my God. Yes. Someone's noticing it.

[Catherine]

Doing the good work.

[Chelsea Handler]

Bye.

[Catherine]

So cute.

[Chelsea Handler]

Oh, wow. That was a quick one. Okay, wow. One and done. All in a day's work, everybody. All in a day's work.

[Catherine]

We'll see you next time.

[Chelsea Handler]

Adios.

[Savannah Guthrie]

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[Chelsea Handler]

[e-mail] a mother's love deserves a gift like no other. Celebrate her love, strength and style with heartfelt jewelry from Pandora. From iconic charms to sparkling necklaces, rings, earrings and more, there are so many ways to say thank you Mom. Pandora even has in store engraving so you can treat your mom to a trip to the store and have your pieces engraved together with your own handwriting. So on Mother's Day and every day, tell her how much she means to you with a gift from Pandora. Visit Pandora in store or [e-mail] in.

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