We have news. Starting in 2018, we're taking a break from making Why Oh Why. While we can't predict the future, let's call it a break not a breakup. For this special episode, we'll hear from a wide range of past guests including David #1, Randy, Bumble Mike, and Mona Chalabi. Then, does your host have a secret boyfriend? In a Twitter survey, 35% of…

This summer, Schuyler shared a playlist of songs that have helped her cope with depression and anxiety. It moved a lot of people in her life to reach out, including Tom. For all the feels, check out the playlists discussed in this week's episode: 1. Eardrummings Vol. 19 by Schuyler. "Here's a playlist of songs that sort of put words/music to how I …

After you've developed an allergy to casual sex, is there a cure? We talk with comedy writer and performer Matteson Perry about keeping things casual. He's the author of "Available: A Memoir of Heartbreak, Hookups, Love and Brunch." Plus, Dr. Chris Donaghue explains the value of a strong sexual connection in the early stages of dating. He's the aut…

Esther Perel has ideas for how to humor yourself on your first dates using a bit of role play. She's the host of the Audible original podcast "Where Should We Begin." You can hear Season 1 of the show on Apple Podcasts, and Season 2 is now available on Audible. She's also the author of "The State of Affairs: Rethinking Infidelity." Plus, our strang…

Live from Chicago Theater Works, our show begins with the love story. Hear how a first date turned into a meaningful relationship for six single women. This story came to us after Lisette's brilliant Twitter thread went viral. Plus, we help an American Ninja Warrior find love the old fashioned way: with a game show. Find out how five single ladies …

On election night last November, the world shifted beneath our feet... but what was going on our bedrooms? Nona Willis Aronowitz is a features editor at Splinter and writes a newsletter called "Fucking Through the Apocalypse." She joins us to discuss sex, politics and woke misogynists in the Trump era.…

Brian has Muscular Dystrophy and gets around in a wheelchair, but that doesn't mean he won't make out with your girlfriend when you're not looking. On today's show, Brian tells his friend Luke what it's like for him to date with a disability. This episode came to us as a suggestion from Luke Terrell. (You might remember him from our LA show? He was…

Ghosting has been called the millennial way of breaking up, but that doesn't make the phenomenon any less haunting for its victims. Just in time for Halloween, we present a collection of ghosting stories from listeners across the country.By Andrea Silenzi

The age gap between men and women in heterosexual dating has become a fact of life in the 21st century. The Guardian’s Mona Chalabi suggests it’s time for that to change. Read her op-ed "I Want My 2.3 Bonus Years" in the New York Times.By Andrea Silenzi

The arm implant, known as Nexplanon, is a birth control option that's slightly more effective than the IUD, and less painful to insert. Why aren't we all using it? Why Oh Why's Lindsey Kratochwill investigates.By Andrea Silenzi

While Hurricane Irma sped towards Miami, Emily decided to ask a guy from Bumble if he wanted to evacuate with her as a 3rd date. Her family has a home in the woods of North Carolina, and they'd be out of town that weekend. Here's what happened after he said yes.By Andrea Silenzi

Helen Zaltzman has a way with words, which is why we're putting her to work solving one of the trickiest parts of online dating—composing your opening messages. Some lines can break the ice, while others just throw more ice into the void. We'll suggest a few ideas that just might work for you. Helen is the host of the The Allusionist podcast, and w…

This week, with Bumble Mike in tow, we set sail on a singles mixer, organized by The League. Is finding a date while stuck on a boat easier than swiping through the apps? And more importantly, who's your favorite yacht rock artist?By Andrea Silenzi

In this episode, we talk to a human shield and a human billboard. First, Al Letson was just trying to cover a demonstration—an anti-hate rally in Berkeley. When he saw a group of balaclava-clad men descend on an apparent right-wing agitator, he jumped into the fray, using his body to defend the man from kicks and punches. Letson is the host of Reve…

Today on the show, we’re finally tackling THE QUESTION we're asked the most frequently as a podcast about dating: "Who should pay for the drink on a first date?" Join us for a Tour De Advice for straight daters, starting with Sarah Bennett, the co-author of F*ck Love, who suggest dating like a headhunter. Then we'll hear from a range of writers inc…

When determining your criteria for a date, how much should height matter? We'll talk to one woman who has always known exactly what she's looking for in a partner. Anna Goldfarb is a journalist and author of the book "Clearly I Didn't Think This Through." She has also written about her relationship for the New York Times. Our sponsors for this epis…

If you can fall in love with anyone, how do you choose well? Mandy Len Catron offers an answer. She's the author of the book How to Fall in Love with Anyone. She also wrote the Modern Love essay "To Fall in Love with Anyone, Do This" for The New York Times, which was one of the top 5 stories the paper ran in 2015. You can try “The 36 Questions That…