40+ Absurd, Awkward, and Cringy First Date Stories Shared by Jimmy Fallon’s Audience

It’s only natural to feel insecure on a date, a setting where you know you’re being judged and scrutinized by the person sitting in front of you. So, to have a boost of confidence on a date, some people like to talk about their exes, about how many exes they’ve had and how good-looking they were. Some people feel like that’s something to brag about!

I can only assume that’s what this guy was going for. He was probably trying to impress his date by showing her pictures of his ex-girlfriends. But why did they have to be naked? Was he trying to prove a point that he dated really good-looking ladies? Obviously, it’s a very cringe-worthy move, and it’s safe to assume they didn’t go on to have a second date!