“I can't make it to my best friend's old lady.”
Tom Cruise - Brian Flanagan

“- Harry Burns: No man can be friends with a woman that he finds attractive. He always wants to have sex with her.
- Sally Albright: So, you're saying that a man can be friends with a woman he finds unattractive?
- Harry Burns: No. You pretty much want to nail 'em too.”
Billy Crystal - Harry Burns
Meg Ryan - Sally Albright

“Sex is the quickest way to ruin a friendship.”
Janeane Garofalo - Vickie Miner

“- Darryl: I never had a sexual thought about your mom until I was 30.
- Brad: Can you leave it alone? You can't be my friend anymore. You can't be sleeping with my mom and still be my friend, ok?”
Patrick Van Horn - Darryl
Vince Vaughn - Brad

“- Maurey Pierce: We're both virgins, but someday we're gonna find ourselves doing it for real.
- Sam Callahan: So today's sex isn't real?
- Maurey Pierce: We're just friends helping each other learn a new skill. This is practice.
- Sam Callahan: So, will we still be virgins afterward?”
Mischa Barton - Maurey Pierce
Bug Hall - Sam Callahan