10. Shoshanna And Her Summer Camp Friend, Season 1, Episode 4
In the beginning of the first season, peppy and innocent Shoshanna (Zosia Mamet) reveals that she's a virgin at 21. She ends up losing her virginity to Ray in the season finale, but this episode shows a chance encounter with a guy she met at summer camp (Skylar Astin). This leads the newfound acquaintances to Shoshanna's bedroom where he promptly goes down on her. She clearly has never experienced this and blurts out that she's a virgin. The guy immediately stops and tells her that virgins aren't his thing because according to him, they get too attached and there's blood involved. "I so don't get attached when I bleed," Shoshanna says. "I'm like totally not an attached bleeder." The he leaves. Awkward.