Jinah’s neighbor Rick has had more than his fair share of dating disasters. From a woman who kicked off their evening by shaving the calluses off her feet, to another who couldn’t stop dropping F-bombs at a nice restaurant, Rick just can’t seem to catch a break. His stories are a snapshot of the cringe, chaos, and comedy we’ve all come to know from modern dating apps. But no matter how many fails he racks up, there are two things about himself Rick refuses to change.

Rejection is part of dating—but on apps, it can feel relentless. A thousand swipes for a single match, only to get ghosted. What used to be competition with a handful of people at a bar is now competition with everyone in your city (or even your state). In this episode, Daniel and Jinah sit down with mental health therapist @iamthatboyphil and writer @ivyeats to unpack the emotional burnout, self-sabotage, and unrealistic expectations that dating apps so often create.

Everyone swears they’ve got it the worst on dating apps — men, women, you name it. But who actually takes the crown for the most tragic (and hilarious) experiences? In this episode, Daniel and Jinah sit down with Ryan Lugo and Akosua Mireku (@poem.a.day.project) to swap war stories from the wild world of online dating. Cringe, laugh, and maybe even cry a little as we ask the ultimate question: is anyone actually winning on these apps?