Love Letters

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

Bailey Watroba, a senior public relations associate at the Boston Public Library who helped build and run the Love Letters phone booth, shares stories from the installation. She discusses why young people are drawn to old tech, how the anonymous payphone works, and the surprising variety of callers—from heartfelt breakups to playful tourist questions. The piece captures the booth as a reflective, analog space in the city.

Dr. Todd Kashdan, psychologist who studies curiosity and social behavior, joins to unpack why people on dating apps often avoid asking questions. He explores how texting, gender norms, and anxiety erode conversational curiosity. The conversation highlights why asking questions is a valuable skill and how structured practice can revive deeper connection.

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

A catch-up about one life built by saying yes to classes, clubs, and goofy activities. Stories about meeting a partner mid-pond-skim and how joining things boosted confidence. Talk of moving, starting a family, and rebuilding community through gardening and a flower business. Reflections on timing, staying adventurous, and keeping shared activities alive after kids.

Yowei Shaw, podcast host and producer who led Proxy and worked on NPR’s Invisibilia, shares a personal story about identity, queerness, and relationship dynamics. She recounts hiding her husband to fit into queer spaces. Short scenes cover early crushes, meeting Kyle, the hot pot moment that exposed her hiding, and her journey from shame toward apology and acceptance.

Last fall, Chanté Joseph wrote an essay with the headline: “Is it embarrassing to have a boyfriend now?” The piece – about the politics of showing off heterosexual relationships – went viral; people debated it all over TikTok and beyond. (Even New York City’s mayor weighed in.)Months later, Meredith and Chanté sit down to discuss why the essay hit so many nerves at once. Some readers hated Chanté's essay and what it suggested about the evolving values of women.Others – namely single straight women – loved that Chanté’s essay highlighted women who are choosing to post pictures of friends instead of significant others.It’s a complicated discussion – and Part 1 in a two-part exploration of why the concept of a boyfriend can be a bit … cringey.This episode features a montage of creators who were inspired by Chanté’s essay. They are, in order of appearance: @thanahit @maryarchived @jedidahbila @JeffHarryPlays @melvinoyx @rollotomassi @boyproblemsshow Learn more about your ad choices. Visit megaphone.fm/adchoices

Justin Garcia, executive director of the Kinsey Institute and author of The Intimate Animal, is an evolutionary biologist who studies sex, relationships, and fidelity. He contrasts social and sexual monogamy. He explains "slow love" and why young people delay commitment. He discusses ways couples sustain intimacy and how modern courtship is shaped by caution and honesty.

A celebration of platonic third-wheeling and why being the extra friend can expand your community. Stories about meeting couples, forming lasting trios, and how timing and boundaries make third-wheeling work. Anecdotes range from hardware store meet-cutes to deep acts of care that reveal how odd-numbered friendships bring balance and safety.

Jazmin Aguilera, podcast producer who recently navigated a breakup, shares her personal story and reflections. She talks about living with an ex, rejoining social media for comfort, and how Venmo’s public feed and algorithms complicate moving on. The conversation covers blocking, digital snooping, and the ways online life can prolong heartbreak.