“- Richie Tozier: What are you saying, Eddie? You're still a virgin?
- Eddie Kaspbrak: Yeah.
- Richie Tozier: Well I can't help you there, pal.”
Harry Anderson - Richie Tozier
Dennis Christopher - Eddie Kaspbrak

“Virgins. I love them. No diseases, no loose as a goose pussy, no skank. No nothing. Just pure pleasure.”
Leo Fitzpatrick - Telly

“- Hannah Wald: Technically I don't think I'm a virgin anymore. This past summer at church camp I think I had my first orgasm.
- Kansas Hill: Any sentence that starts with church camp ain't leading to the big O.”
Rachel Blanchard - Hannah Wald
Mena Suvari - Kansas Hill

“Holy hymens, Batman - they're killing virgins!”
Keram Malicki-Sánchez - Timmy

“- Eliot: Are you telling me I popped your cherry?
- Vivian: I didn't want to make a big deal out of it. I just wanted to get it over with. No ceremony.
- Eliot: That puts a lot of pressure on a man. Did you think of that? Did you think of me? You know what this makes me? A criminal. On 2 counts! Devirginizing a minor.”

Kevin Corrigan - Eliot
Natasha Lyonne - Vivian