An introspective look at modern dating

One of the things that makes Why Oh Why? so special is its sense of continuity. Andrea Silenzi isn’t just using her podcast to examine the peculiarities of dating; she’s also using it to tell stories and build communities. In an episode a few weeks ago, she sent Kate, a friend of hers, on a date with David, a friend of the show, then recorded their conversation to gauge how her “meddling” would alter the texture of the evening. Things took an unfortunate turn, however, when it was revealed that Kate had booked a Tinder meet-up to immediately follow her date with David, and the two ended up colliding in a maelstrom of awkwardness. For the latest episode, Silenzi invites David into the studio so the two can have a post-mortem about the evening, which includes reading online responses to the episode. David responds with grace, even as the two attempt to understand Kate’s reasoning for booking the other date. He also offers a smart, reasoned response to a listener who worries about whether the situation truly proves that “nice guys finish last.” Through it all, Silenzi plays back the cringe-inducing clips, which include a forced goodbye the duo had