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 our listeners thought this was a possibility.

Say in touch! Follow @andreasilenzi on Twitter and Instagram and check out her new show, The Longest Shortest Time.

#58: Just Another Sad Love Song

This summer, Schuyler shared a playlist of songs that help 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 feel during my lowest lows. These sounds help me swim my way through that almost-drowning sensation and find my way back to a place that feels safer and clearer."
2. Songs Schuyler Might Like by Tom
3. Songs Tom Might Like by Schuyler
4. Songs from Episode 58 by Andrea

#57: Casual

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 author of "Sex Outside the Lines" and co-host of LoveLine with Amber Rose

#56: Stage a Fight with Esther Perel

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."

#55: Live in Chicago - Find Your Single Ladies

Live from Chicago Theater Works, our show begins with a love story. Hear how a first date turned into a meaningful relationship for six single women. Plus, we help an American Ninja Warrior find love the old fashioned way: with a game show. Find out how five single ladies from our Chicago audience fare when we ask them real questions from the 1960s TV show The Dating Game.


#54: End of the World Sex

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.

#53: Dating While Brian

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.

#52: Horrible Anonymous

You know that hit podcast where a comedian talks with an anonymous person for an hour, no holds barred? We love that show! That's why we wanted to try our own version. What could possibly go wrong...

#51: Ghosting Stories

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.

#50: Stop Dating Older Guys

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. 

Graphic by Mona Chalabi, based on data from Christian Rudder's Dataclysm. Originally appeared in the New York Times. 

Graphic by Mona Chalabi, based on data from Christian Rudder's Dataclysm. Originally appeared in the New York Times.