In 2016 and 2017, Andrea Silenzi hosted and produced the hit dating podcast Why Oh Why, with the mission to chronicle her hilarious, maddening, and sometimes disastrous expedition into online dating. For guy listeners like me, it was also a window into what single women had to put up with when they were looking for love (or even just a decent date) on the internet. Her excruciatingly detailed exploration of how men and women approach digital courtship led Vulture to dub her “a genius of the cringe.”
After the show went on hiatus, Silenzi continued to post about the horrors of online dating on her Instagram account, a lifeline for fans who missed the show. But this past week, something else appeared on the account: She posted a very sweet engagement story, announcing her impending nuptials to a man reportedly from Hinge. How could this happen? Who will post screenshots of men saying things like “Yeah i got the cure for coronavirus! Deez Nuts!”? I called Silenzi to ask. Our conversation has been lightly condensed and edited for clarity.
Aymann Ismail: Congrats on the engagement! I’m excited for you. Do you think your escapades online affected your decision to settle down with Dan?
Andrea Silenzi: We both lived in New York at around the same time, riding the same train, going to similar bars, probably watching the same TV shows and movies. He’s someone I could have met, and even though I love every day with him, we are so glad we didn’t meet then. We really had to have met now after we learned all the lessons. Our past experiences make us that much more sure. And I just feel like having him in my life, we’re just set up for a future together, where we won’t keep wondering if I just kept shopping a little longer, I would’ve found someone more my size.
I’m also very jealous of people who get to grow up with their partner. The two of you can enter adulthood together, adopt your first dog together, move to your first new city together. And Dan and I never got to do all of that stuff. We never got to know each other when we were 25 and required less sleep. But I think that that’s OK, because I don’t know if we’ll ever run out of dating stories.
I imagine your fiancé, when he was pre-fiancé, listening to Why Oh Why, digging for clues when he figured out who you are.
He Googled me when he matched with me. And then his first Google result was from a series I was working on where I was “sperm shopping.” Dan’s best friends found that same quote, showed it to Dan, and told him, “Oh, no, she’s out for your sperm!”
He really had to take the time to figure out the nuance of what I was talking about, which was me contemplating single motherhood. So it was a lot to take in and I’m just grateful he took the time to read it all and not just go, “This is too weird.” I feel like there was always a part of me hoping that the show would work like a siren call, because I was trying so hard to be so authentically me.
Will any part of you miss the dating grind?
I had a moment recently where I was doing volunteer work and I noticed someone in the room that I would be interested in, in any other life. And it was realizing that I didn’t want to acquire his attention or form any kind of connection with that person was kind of the moment I realized, “Oh, wow, I’m really off—I’m really exiting this market.” I don’t know if I wanted that. I mean, I do know I want that, but it’s kind of hard. That little first flutter. It’s a hard thing to say, “Wow, there won’t be flutters.”
You think? I mean, I feel you, and it’s a real feeling. But it’s impossible not to get flutters for people. It’s just how you handle it that makes the difference.
Yeah. It’s not the end of crushes, but it’s the end of wanting to act on them.
This year I purchased my own show back from what was formerly the Panoply network and is now a hosting technology company called Megaphone. And I don’t know what I’m going to do with it yet. It’s been nice to take a moment to tell other people’s stories at my current job at Spotify right now. But when I’m ready to start making art again, I will.
This is the thing. I don’t believe I should get to be a dating expert anymore. My favorite kind of dating expert is someone who is a correspondent from their own lonely heart. I’m still figuring it out. If anything, I would call myself a “relationship expert.” I can imagine expanding the show into a new thing.
If people hadn’t heard the show, how would you describe what you did with Why Oh Why?
Why Oh Why is a show I started in 2016 while in a happy relationship. And it turned into a show where I became a correspondent for my own broken heart because of a breakup that I went through that year, but also just the way the world changed as we entered 2017. So it was part personal diary, part dating advice, and I would often call myself a “dating expert,” again never without the quotes.
I definitely took advantage of the intimacy of the podcast medium. I found a subject matter that is best to talk about kind of over group text with your closest friends, over late-night drinks, and I made it a really personal conversation with other people who were feeling the way I was feeling at the time. I definitely made it for other single people, because I was finding that a lot of relationship advice experts were married. And when married people talk about dating advice, just—they weren’t coming at it from a place of starvation. They were fully satiated saying, “You too can also have a four-course meal.”
I was engaged—soon to be married—when I was listening to your podcast, and I felt like I was vicariously living through you. I missed the whole dating app era. At that time, I would download Tinder just for fun to see what was on there, then real quick delete it in shame.
I feel like whenever I told married people what I was going through in my dating life, they all made the same face—that face the best friend made in When Harry Met Sally, their eyes are just like, “Tell me I never have to be out there again.” I’m kind of curious if, when you were listening, it helped your marriage in that you could look at this person on just some random Tuesday and be like, “Wow, I don’t have to be out there.”
I learned a lot about the way people look for love, you know? And I would take some of that and apply it to my relationship. Like how it takes a little bit of extra effort to first know how I feel, and then communicate how I’m feeling in a way that my partner will understand. So it made me think more deliberately about how I was communicating. But yes, you shared some hilarious, sometimes horrifying experiences and I’d tell her, “Thank God I’m not using those apps.” How long were you using them?
So when I started the podcast, I think we were still having an app boom. Apps were considered the cool new thing. At that moment, I was just downloading every single dating app I could find and staring at them wondering, How could these tools help me, and will they live up to their promise? And then they became a really vital tool in my life after a breakup in 2016.
How so? You wouldn’t necessarily have gotten that from the Instagram—
I think that you can learn a lot about yourself through the shopping part of online dating, similar to how you don’t really know what kind of couch you like until you start shopping for your first couch, because you never really had to think about couches. I think your profile helps you learn who you are and what matters to you and a partner. And once you start to learn those lessons in this digital space, you apply that to your real life. So it might make you more willing to say hello to someone at a coffee shop because you know you love a dude with a messenger bag and glasses.
I found through my partner that there’s a thing called the triple B—a guy with a beard, a beanie, and a book. That’s supposed to be a keeper.
Oh, man, books. There are so many things I would do as a single guy. If I wanted someone, one of the first things I would do is sit at a cool Brooklyn bar with a book. Any book. A phone book would do.
To break your own engaged-person rule, do you have any advice for people still doing the dating app grind?
My advice for people still using them is don’t do what I do and just be on all of them, kind of carelessly taking screenshots and looking for things to hate about people. My advice would be to do it in a way where you’re looking for things to love about other people. There are so many things to be sad and upset about right now. So if you make it an exercise to say, “Oh, he has a cool shirt.” Or “Oh, that’s a great dog!”—as hard as it is—if you start looking for the kinds of people who share your values, you will find them. And there’s no reason not to ask them for a phone call before the first date.
What about what not to do?
Definitely show your profile to at least one other person in your life. Do it like a job application you want a friend to read, with your eyes closed in the middle of the night at like 3 in the morning. I think it can make you feel so vulnerable to have even made one. You just feel like the moment you finish it, you’re putting yourself out to be judged by people, and that’s such a weird, abnormal feeling. But if you can share it with one other person, they can make sure you’re being honest about who you are and how you’re advertising yourself. I think there’s a temptation to sometimes be like, “I’m really into horseback riding,” when you’ve barely ridden a horse. Definitely don’t.
Are you gonna miss trolling people on the apps?
My partner and I love to do it together. He’s almost more into it than I am. I feel like I knew we were at a really intimate place in our relationship when he grabbed my phone and took it with him into the bathroom and then screengrabbed profiles for us to write captions for my Instagram later. We’ll never delete the app because for me it’s like a lens into this very subtle window for what single women are experiencing in their dating lives.
I love to draw attention to a guy who says, “I can’t wait to meet someone so she can show me how to fold a fitted sheet.” I’m like, “Oh, great. You need a woman to teach you something domestic? Try Google!” Or you’ll see someone who just hasn’t bothered to fill out the most basic questions of his dating profile. You wouldn’t mail a job application without work experience. You’re just, like, gonna fill this in later?
It sounds like the best dating advice you can give someone is have a podcast about your dating life.
Oh, no, it definitely did not help me. The best dating advice I could give someone is take it seriously. Go on lots of dates. It was only the moment I stopped making podcasts that I was able to meet Dan. Our first date was on a Sunday night before my first week without a podcast job. And I really think that that was part of it. I was finally off the deadline, and I didn’t have to treat my dating life like a reporting initiative, so my dating life just became something I was doing for me.
That makes total sense to me, as someone who has also put a lot of himself into his work.
When I was doing my dating podcast, I interviewed an author who told me that getting engaged and married to his wife was like being an athlete who was retiring at the peak of his abilities. The moment he got engaged, he couldn’t do what he did best, which in his case was seducing women at bars. He did it so well that he found his wife and then he got to retire.
For me, it feels closer to leveling up in a video game where I had been at Level, I don’t know, Level 2 forever. And Level 3 was going to be easier, but I couldn’t solve it. I couldn’t solve it. I asked everyone in my life, “How do I get to Level 3?” I got so frustrated. I was like, Maybe I’ll just stay at Level 2 forever. And now that I’m on the other side—you know, insert some chimes here—I’m like, Wow, it’s pretty nice and easy here. You have this other person who’s just as invested in your future happiness as you are, who wants you to achieve your dream, who’s going to help you do that. You get to share the cost of toilet paper and paper towels with another person. You get to have them there for you forever. It’s just fucking crazy. I just—I’m not retiring. I’m just at an easier level.
You should print that on pamphlets and hand them out on the street.
I’m sure there’s going to be obstacles in Level 3. I could get bumped back down to Level 2 at some point. Maybe I’ll get to Level 7? I feel like I now have new powers. I can jump higher and run faster. And you stupid married people were pretending like it was OK for me to be a Level 2, like, “You can stay at Level 2. Level 2 is actually not that bad. You have so much freedom.” I feel like I’ve been misled.