A Podcast or Two (or Five) to Keep Your Mind Off Your Singleness on Valentine’s Day

"Hopefully, listening to all of these episodes will help you survive until February 15th when the chocolate at CVS is finally on sale."

by Adam De Guire


Call me odd, but when I feel lonely I often distract myself by grabbing my headphones, turning on a podcast, and going for a walk. It gets me out of the house and increases my chances at a meet-cute with a Clintonville yuppie out walking their dog.

That hasn’t worked out yet, but in the meantime I’ll recommend some of my favorite podcasts and episodes about love, dating, and sex to give you something to listen to while you wait for the chocolate to go on sale at CVS.

Why Oh Why

I’ve been listening to Why Oh Why since it was an hour-long radio show on WFMU, a free-form community radio station based in New York City. Now that it’s been rebirthed as a podcast on the Panoply network, I recommend it to anyone who feels dispirited by modern dating because the host, Andrea Silenzi, has been there in the pits of Tinder, Bumble, and OK Cupid, and understands how hard it is to find even just a date, let alone romance and love. But, the show amounts to more than just millennials feeling sorry for themselves, because it looks at other aspects of modern dating, such as IUDs (Hacking the Uterus 2.0 - 49:02), the sound design of Tinder (Listen to Your Heart - 20:16), and deconstructing the awkwardness of a first date (Can Meddling Help a First Date? - 26:09).

(Oh, but keep an ear out for Randy, the vilest radio villain in history. I cannot stand him, even though I think I understand what Andrea is doing by having him on her show.)

Star Episode: How Will I Know (22:18)

Just a warning, this episode is about Andrea’s reaction to her breakup with her boyfriend. But, I’ve listened to this episode probably four or five times, that’s how good it is. I think it also helped that I went through a rough patch in my dating life right around when the episode was released, so I could commiserate. I think, though, that Andrea’s storytelling mixed with tape of an interview of her with her producer adds up to an emotionally satisfying look into how a breakup can surprise you, both in how it happens and how you feel about it, but without dipping too far into the well of breakup clichés.

Runner-up episode: Too Old for Meet Cute (24:13)

A woman has an awkward date with a tequila-drinking, Blow Pop-eating man. It is not the meet-cute she imagined.

Heavyweight - Galit

Do you remember your first love? The one when you were young and felt like you finally knew what it felt like to be accepted by someone and the world was open to explore and nothing could go wrong? Do you remember when it went wrong? Have you ever gone back and talked to that person about it, years and years later?

Well, Jonathan Goldstein, host of Gimlet Media’s exceptional and emotional show Heavyweight, did just that in this episode, Galit (32:42). Among a string of standout episodes in Heavyweight’s first season, this one stands a head above.

Heavyweight is almost always funny, and this episode does exhibit Jonathan Goldstein’s hallmark dry humor, but it also hits hard in emotional content. It brought me back to feeling like a teen-aged romantic, but also reminded me that it’s the heartbreaks that helped make me who I am.

Sex Lives Podcast - Sex and the Single 42-Year-Old Woman

At this point, you’re about an hour into your CVS trip and it’s becoming fairly obvious that 1) the chocolate at CVS isn’t going to be on sale any sooner if you keep checking it every 5 minutes and 2) the cashier is beginning to eye you very suspiciously, so you should probably give up on it. And maybe you’re ready to give up on dating in general and you’re fantasizing about all the fucks you will not give once you’ve given up trying to impress anyone. What does that really look like, a life of being single? What does it look like when you’re 40 and your friends are all married and/or having children? What does it look like to still be a sexually liberated person at 40?

Glynnis MacNicol gives her insight to the single life at 40 in the episode of New York Magazine’s Sex Lives podcast, Sex and the Single 42-Year-Old Woman (35:39). It opens with being propositioned for sex by a 19-year-old Montana cowboy, and broaches topics such as being the “default” emergency caregiver for your aging parents and your friends’ and siblings’ children. It’s nice to be reminded that being single doesn’t necessarily lead to a life of loneliness and fear of choking to death alone in your apartment.

Now, I don’t want all of these to be about breakups or being single, so let’s transition to some podcasts about seeking relationships and some of the activities you might partake in once you find someone special (or at least someone willing — that can be half the battle, let’s be honest).


Did you know Tinder has a podcast? Well, they paid for a podcast anyway. It’s a sponsored podcast called DTR (short for “define the relationship”, that dreaded conversation that I feel like I’ve only ever had once it was clear the relationship’s demise was imminent). It’s produced by Gimlet Creative, the sponsored content arm of the company behind Heavyweight (see above), so you know it’s well-produced. But, it is a marketing mouthpiece for Tinder, so it focuses more-or-less exclusively on the app (personally, I don’t think it sells the app very well, but I’m also a bit of a traditionalist — I prefer to flirt face-to-face. I like to think my awkwardness is endearing in person, instead of off-putting).

Star Episode: Hey

If you want to ask someone out (whether in person or on Tinder), you have to start a conversation. And let’s face it: you don’t always have a clever quip close at hand to spark things off. So, many resort to the ubiquitous “Hey”. This episode takes a deeper look into the phenomenon, and suggests a better go-to opener, this skeleton pizza delivery gif:

The Heart

The Heart is a podcast that I reserve for listening to in my apartment, preferably when no one else is home and, even then, in my room laying in my bed with the lights down. That is to say, it’s often steamy.

But, like any good podcast, it keeps surprising me. One of the most intense podcast episodes I’ve ever listened to was the award-winning “Mariya”, which originally aired on the venerable This American Life. It’s about female genital mutilation and it is hard to get through at points, but it is also very helpful in realizing that this still happens in our modern age.

They also produced a series called “silent evidence” about a woman dealing with her childhood sexual assault that I consider required listening. Again, it’s difficult to listen to at times, but only because it forces you to confront how terrible the world can be.

Star Episode: That Smell (6:05)

Just try not to get turned on listening to this one.

Runner-Up Episode: Twirl (20:07)

This one isn’t about sex, but I like it anyway because it typifies The Heart’s unique approach to sexuality and its variety of challenges.

2nd Runner-Up Episode: Idiot + Dummy (20:16) Sometimes falling in love makes you feel dumb, and sometimes you realize later that you were just dumb.

Hopefully, listening to all of these episodes will help you survive until February 15th when the chocolate at CVS is finally on sale. Who knows, maybe that one cashier you have a crush on will be working and you can try out your “Hey.” It’d be a great meet-cute.

Adam De Guire is single this Valentine's Day and no, he won't go out with your roommate/cousin/co-worker/sibling/child, even though he's sure they really are as great as you say they are.