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Updated 24 Feb
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3 days ago

Olivia Wilde on awkward relationships, marriage, and Esther Perel

She directed and co-stars in “The Invite,” a film about two couples who have a fairly monumental, impromptu dinner. It’s a comedy that turns into a drama … and then back to a comedy. It also stars Seth Rogen, Penelope Cruz, and Edward Norton. Meredith saw “The Invite” and thought, "Oh, this should be part of a Love Letters Film Festival, if we ever had one." Today Meredith is joined by Olivia for a discussion about many things, including: why we like to see couples be awkward, Gen Z and technology, polyamory in Massachusetts, the meaning of marriage in 2026, how to stay optimistic about love, and, most importantly, their experiences with psychotherapist and podcast Esther Perel. Meredith and Olivia both have personal connections to Perel, who served as an adviser on the film. Enjoy a lively conversation about love and the stories we tell about it.Also, an event reminder! You can also sign up to attend Meredith’s free June 30th phone booth event – a 6 p.m. celebration of the Tell-A-Booth (featured on the pod) – by visiting bpl.org. Remember, Love Letters is also an advice column. Feel free to tell us your anonymous questions about your relationship life my emailing loveletters@globe.com. Learn more about your ad choices. Visit megaphone.fm/adchoices

3 days ago

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42 min
9 June

When to get off that train, with Drag Queen Jujubee

Jujubee, the boisterous drag queen and fan favorite on “RuPaul’s Drag Race,” is the alter-ego of Airline Inthyrath, a relatively introverted homebody from Massachusetts. In this episode, Airline tells us a story about a recent relationship – and the lessons that came with it. In short: sometimes it’s difficult to be present. Other times it’s hard to know when to stop that relationship train. Learn all about Airline – and then see Jujubee in “Stop! That! Train!,” a new movie directed by Adam Shankman, who made the musicals “Hairspray” and “Rock of Ages.” The movie also stars RuPaul as the President of the United States. Learn more about your ad choices. Visit megaphone.fm/adchoices

9 June

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37 min
26 May

Ruhama Wolle on bridesmaids and ‘bestie inflation’

Welcome to summer wedding season.To celebrate, Meredith interviews Ruhama Wolle, the author of “I Hope You Elope: A Bridesmaid Survival Guide.”Ruhama says too may people say “yes” to being a bridesmaid before they understand the job. This is why weddings can turn friends against one another.Join Meredith and Ruhama for a discussion about wedding costs (financial and emotional), alternatives to traditions, and how to take care of yourself during someone else’s celebration of love.Remember Love Letters is an advice column. Send your questions about relationships to loveletters@boston.com. Get Meredith’s newsletter at Boston.com/meredith. Learn more about your ad choices. Visit megaphone.fm/adchoices

26 May

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40 min
14 Apr

Why Don't Men Ask Questions?

Really? What’s up with that?Simone, a single mom in her 40s, wrote to the Love Letters advice column asking, “Why don’t men on dating apps ask me any questions?” Simone said these men are happy to answer questions about themselves, but they don’t ask anything in return.That means Simone has to do so much work to keep the conversation going.Simone tells her story to Meredith, who also gets feedback and context from experts who study curiosity and the art of asking questions. They include Todd Kashdan, director of the Well-Being Laboratory at George Mason University.He helps Meredith examine the gender piece of it all, the cultural influences, and why asking questions is a beautiful skill – and, perhaps, a lost art.Remember, Love Letters is an advice column that LOVES questions. Do you have something on your mind about your relationship life? Email it to loveletters@boston.com or visit boston.com/loveletters. Learn more about your ad choices. Visit megaphone.fm/adchoices

14 Apr

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33 min
Season 1, Episode 1

EPISODE 1: Officer Pastillas

On the docks of New Bedford, Massachusetts, whispers about a rogue police officer harassing fishermen and stealing drugs come to a head aboard a scalloping boat late one night. The officer forces his way on board, saying an informant told him there would be drugs on board, and demands some. But when another officer, Mark Raposo, shows up, he thinks his colleague is in the middle of a “drug rip.” Now Raposo is ready to blow the whistle on what he’s seen. And it turns out that this officer’s abuse of the informant system is just the tip of the iceberg in this historic port city. *Note: this episode was updated Mar 12, 2025, to include a statement from police that the Globe received after the deadline. Learn more about your ad choices. Visit megaphone.fm/adchoices

S1, E1

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53 min
12 May

What's wrong with having a type?

When Jordan was young, he saw actress Janeane Garofalo on television. Since then, he’s had a type: smart, creative, sardonic, sarcastic, brunette, glasses-wearing women. Not a bad thing … or is it limiting? What does it mean when we have a type? If our type doesn’t like us back, do we have to expand our parameters when looking for love? Take a journey with Meredith and Jordan through an exploration of types ... and the perfection of the woman who starred in “Reality Bites,” and “The Truth About Cats and Dogs,” and made a memorable guest appearance on “The Adventures of Pete & Pete.” Share your thoughts on this episode by emailing loveletters@boston.com. Tell us all about your type – or share your relationship questions. Remember, we’re an advice column, too. Learn more about your ad choices. Visit megaphone.fm/adchoices

12 May

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35 min
31 Mar

"Gettin' After It Together"

We get a big update from Nicole, a guest who once explained an era of her life when she took a zillion classes – and signed up for countless activities (dragon boat racing, included) – to try to meet a boyfriend. Where is Nicole now? She tells us all about life after those classes, and why she wishes she could take more of them now. Join Meredith and Nicole for a sweet update about getting what you want – and what it means to keep learning and participating. Learn more about your ad choices. Visit megaphone.fm/adchoices

31 Mar

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42 min
28 Apr

The Phone Booth

Come by the Boston Public Library June 30th at 6pm for a celebration of the Tell-a-booth! https://bpl.bibliocommons.com/events/6a0f3efffab4ff0f649aaf51 In February, Meredith unveiled a Love Letters Tell-A-Booth at The Boston Public Library.More than 1,000 calls have come in already … mostly from locals – and many tourists – who stop in, enter the booth, and leave a question on an old-school payphone.What can we learn from an anonymous phone booth where people can ask anything? Meredith explains by sharing messages from the booth, and by processing the experience with public library staffer Bailey Watroba, who has thoughts about why young people love old technology.Remember, Love Letters is also an advice column. Send a question about romance, friendships, marriage, breakups, dating fatigue to loveletters@boston.com.You can also submit your own stories to the podcast at that address. Learn more about your ad choices. Visit megaphone.fm/adchoices

28 Apr

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36 min
7 Apr · Bonus

Meredith and Margaret on Lindy West and “Adult Braces”

Meredith talks to former Love Letters guest Margaret H. Willison about “Adult Braces,” a new memoir by feminist writer Lindy West that has sparked big debate about West’s polyamorous relationship.West – who also wrote “Shrill” (which became a Hulu show) – says in this new book that she didn’t want to be in a non-monogamous relationship … but is now happy being one of three. But some readers/fans of West have found this happiness hard to believe.The book reminded Meredith of Margaret’s episode, which was about a complicated non-monogamous relationship that did not work out for Margaret.If you haven’t read the book, that’s OK. Meredith and Margaret will explain the conversation, and how critiques of the book have revealed what we expect of other people’s love stories.Margaret also gives an update on her love life, which is more calm than it used to be. Learn more about your ad choices. Visit megaphone.fm/adchoices

7 Apr · Bonus

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1hr 6min
Season 1, Episode 2

EPISODE 2: Blind Trust

Spotlight reporter Dugan Arnett receives a desperate phone call from an informant who’s now in prison. He says he's afraid for his life because other inmates know he cooperated with police. This informant always knew he’d be in danger if someone from his gang found out that he was a snitch. What he didn’t anticipate was being betrayed by police, including a New Bedford officer who shares information with a member of the informant's gang. Learn more about your ad choices. Visit megaphone.fm/adchoices

S1, E2

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41 min

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