Tim (Paul Rudd, "I Love You, Man") is in an awkward spot.
First, there's a not-quite-requited love for Julie (Stephanie Szostak, "The Devil Wears Prada"), his somewhat-exotic girlfriend. Julie loves Tim, but can't quite commit, despite her boyfriend's repeated efforts to whip out a ring and make an honest woman of her.
Julie and Tim are very much opposites (crazy, right!?), and his straitlaced ways are countered by her job as a curator for a local art gallery, where she mingles at after-hours exhibit openings with weirdo artists.
Then there's Tim's professional life. A lowly analyst at a financial firm, he is vying for a promotion and doing his damnedest to impress the suits on the executive floor, especially big boss Lance Fender (Bruce Greenwood, "Star Trek"), who holds the keys to the kingdom and keeps company with smarmy account execs like Caldwell (Ron Livingston, TV's "Defying Gravity").
Eager to show off his entrepreneurial spirit to the boss brigade, Tim comes up with a plan for wooing a wealthy Swiss industrialist named M