What Is Why Oh Why?

When I started dating my husband in 2001, when we were sophomores in college, neither of us even had a cell phone. It would be three years before we even had our own flip phones. We flirted over Instant Messenger, called each other’s parents’ phones when we were home on breaks, and went on dates to the dining hall and keg parties where we just ran into other people we knew because there was no way to tell someone where you would be for the evening after you had left your dorm room. So for me, Why Oh Why, a podcast about the culture of dating in 2017, lets me be a voyeur into the a world of swiping left or right, Facebook stalking, and the etiquette of whether “hey” is an appropriate  opening text message to someone you’re interested in. 

Host Andrea Silenzi approaches each show with a similar set of big questions about the complexities of love and the paradox of choice inherent to dating in the age of social media. As a single New Yorker in her early 30’s, she’s trying to answer these questions for herself much as she is for her audience, and the answers that emerge in each episode are funny, honest, and sometimes heartbreaking. Like Aziz Ansari’s Modern Romance, Why Oh Why takes on a complicated topic with a combination of thorough research, humor, and experimentation. Silenzi approaches the topic of finding love from every possible angle: interviews with data experts (episode 35), focus groups with single straight ladies (#13) and aspiring dads (#26), and candid conversations with writers about what questions to ask to fall in love with anyone (#41) and why men get a “bonus” 2.3 years in their 20s (#50)

Why Oh Why also does some genre-bending episodes, though as the listener you’re not always certain what’s real and what’s not. One recurring fictional character,  Randy, is the antithesis of the Brooklyn hipsters I imagine Silenzi runs into a lot in her real dating life. He’s tough to nail down, alternating between the confidence of a modern-day Don Draper and the cringe-factor of a creepy coworker who’s always saying things you should report to HR. He seems to have genuine affection for Silenzi and will occasionally give her some actually-decent blunt advice, but just when you think you have a handle on him, he’ll do a bunch of speed and drive from D.C. to New York and then talk about how women should dress sluttier. There’s part of me that thinks we’re Silenzi’s guinea pigs and she doesn’t have a grand plan or exact social commentary in mind with the fictional episodes, and another part that thinks she’s a brilliant genius.

I recommend starting with a tour of Why Oh Why that skips around to a few different kinds of episodes, and these four are some of my favorites:

  • Aspiring Dads Focus Group (#26) is eye-opening in terms of what these dudes don’t think about (and don’t have to think about, like turning 35).
  • Data-ing (#35), where Andrea interviews Seth Stephens-Davidowitz, author of “Everybody Lies: Big Data, New Data, and What the Internet Can Tell Us About Who We Really Are” and they take a deep dive into what people say they want versus what their dating app behavior says they really want.
  • Leagues Over The Seas (#46)  is one of my favorite episodes: Andrea and a  guy friend go on a yacht for an exclusive event sponsored by the dating app The League. This episode has everything: a doe-eyed late-twenties girl who thinks she has it together, some finance bros who you want to throw overboard, and a sassy bartender.
  • Randy’s Mema Died (#16) includes a stream-of-consciousness, unhinged rant that reveals Randy’s childhood dreams, possible sociopathic tendencies, and potential stimulant-induced mania. You’ll know from this episode if you’re all in for the Randy episodes or not, but he had me hooked when he named his fantasy/real estate investment opportunity/weirdly detailed scheme/waterpark  Ragin’ Effin Insanity.

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