In Van Wilder (2002), Van Wilder gave a party to all the students, After hearing underage drinking was going on, cops came and arrest him. Behind this, Richard is the one who caused him being arrested by sending kids to the party. Jeannie is Richard's assistant but she reveals the truth to Gwen about who was behind it after Van Wilder wins the case.

Gwen: Hey, Jeannie.

Jeannie: Look, Gwen, I just wanted to explain about the whole, you know, Richard thing. Me and Richard's unspoken bond blossomed the other night in one beautiful. Symbiotic act.

Gwen: What sort of act?

Jeannie: Messing up that Van Wilder party. And then we bumped uglies. It was the best ten seconds ever. Ever.

Why did Jeannie reveal it even though she is Richard's assistant?

up vote 5 down vote accepted

Jeannie isn't Richard's "assistant" as such although she is involved in his nefarious plans...she wants to be his girlfriend and replace Gwen in his affections.

What Jeannie is doing is taunting Gwen by telling her that she (Jeannie) had sex with Richard and then helped him with his plans.

Essentially, she's rubbing her new relationship with Richard in Gwen's face.

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