4. Jessa Rebuffs Her Boss Jeff (Episode 7, 'Welcome to Bushwick')
"Oh my God, I'm that guy," Jeff moans after arriving at the massive Bushwick warehouse party to Jessa’s awkward surprise. And that’s before he gets beaten up and ends up in the E.R.! Despite that moment of self-realization, Jeff still tries to get Jessa to go home with him, calling her a "tease" through a bleeding nose when she turns him down. Not as cringe-worthy as the off-screen moment when he has to tell his wife what the hell happened to him, but still . . . yikes.