“- Chazz Reinhold: So how's my protégé?
- John Beckwith: Jeremy, believe it or not, is getting married!
- Chazz Reinhold: What? What an idiot! What a loser! Good! Good! More for you and me.”
Will Ferrell - Chazz Reinhold
Owen Wilson - John Beckwith

“- Dave Martin: Don't do anything stupid.
- Oz Oseransky: Why would you say that?
- Dave Martin: You married Sophie.”
Howard Bilerman - Dave Martin
Matthew Perry - Oz Oseransky

“You fuck dumb. You don't marry dumb.”
Allison Janney - LaVona

“- Pigeon Lady: The man I loved fell out of love with me. That broke my heart. When the chance to be loved came along again, I ran away from it. I stopped trusting people.
- Kevin McCallister: No offense, but that seems like sort of a dumb thing to do.”
Brenda Fricker - Pigeon Lady
Macaulay Culkin - Kevin McCallister

“For the first time in my life, I was in love. And I knew it would last forever... Boy, was I a dumb ass.”
Ben Foster - Berke Landers