“- Patrick Verona: Some asshole paid me to take out this really great girl.
- Katarina Stratford: Is that right?
- Patrick Verona: Yeah, but I screwed up. I, um, I fell for her.”
Heath Ledger - Patrick Verona
Julia Stiles - Katarina Stradford

“- Oscar Novak: As soon as we left the gallery, our cab caught on fire. Then, she elbowed me in the face. Then, we both threw up. Then, she slammed a car handle into my balls, okay? The entire night was a total disaster.
- Peter Steinberg: You're in love with her.
- Oscar Novak: Pretty much.”

Matthew Perry - Oscar Novak
Oliver Platt - Peter Steinberg

“- Giselle: Oh, you have such strange ideas about love.
- Robert Philip: Maybe we should just do what you do. You meet, you have lunch, and you get married.
- Giselle: Oh, you forgot about happily ever after.
- Robert Philip: Forget about happily ever after, it doesn't exist.”
Patrick Dempsey - Robert Philip
Amy Adams - Giselle

“- Paula Mann: Sharon, baby, do you think you should go out with a man? I mean... so soon after your ordeal and all?
- Sharon Winters: So, I was raped. It happended six week ago. What do you expect me to do? Observe a year of mouring?
- Paula Mann: Baby, please I didn't mean to bug you or make you mad.”
Sharon Carr - Paula Mann
Stacey Walker - Sharon Winters

“Speaking of shoes. You know what I was thinking I'm... You know I, I would like to have a... some shoes next to my shoes.”

Robert De Niro - Detective Eddie Flemming