Michael Felgate (Grant) is a bumbling, well-meaning Brit working in America for the Cromwell Auction House. Felgate unwittingly gets involved with the local Mob through his relationship and eventual wedding engagement with Gina (Jeanne Tripplehorn), whose father Frank Vitale (Caan) is a mafia kingpin. By the time Felgate realizes what Frank's business really is, he's too much in love with Gina and already too deep within the Vitale Family to easily get out of trouble.
- Auction: Much of the action takes place at an auction house.
- Auction of Evil: Felgate's business is auctioning art. When the Vitale family uses its connection to Felgate to launder money the art auctions start becoming this.
- Batman Gambit: Gina Vitale pulls this one when she momentarily fakes her death with the feds' help to solve the plot.
- Big Applesauce: The film is set in New York.
- Big Secret: The reason Gina rejects Michael's marriage proposal at first.
- Comically Missing the Point:
- Michael sure takes a lot of time to realize the Vitales are mafiosi even though the clues are everywhere.
- Frank's speech about how daughter Gina deserves the best:Frank: [talking about her daughter] She met someone who knows exactly how she deserves to be treated.
Frank: Like a fucking princess.
- Department of Redundancy Department: Frank's business front is an Italian restaurant called The La Trattoria, The and La meaning the same thing in different languages. Possibly intentional, as the movie also ends on a "The The End".
- Distracted by the Sexy: Since Felgate is worried that Gina dumps him if she finds out that her dad's Mob is infiltrating the auction business, he then tries to pull this trope to keep her from seeing the evidence.
- Fake American: In-universe. Felgate tries to pass for an American a couple of times. Hilarity Ensues.
- Faking the Dead: Gina's Batman Gambit involves faking her death for a while
- Failed a Spot Check: Again, Felgate is unable to take all the obvious hints about Frank & family until Gina has to spell it out for him.
- The Family for the Whole Family: The Mafia is played for laughs and never pull a single hit.
- Fish out of Water: Michael tries to adapt to the Vitales to keep up certain appearances.
- Hot Teacher: Gina, who works as a schoolteacher and is played by Jeanne Tripplehorn.
- The Mafia: Frank is a member.
- Mafia Princess: Gina is this to Frank and later to Michael.
- Ooh, Me Accent's Slipping: Michael when trying to speak like an American gangster.
- Pinball Projectile: Gina accidentally to Johnny.
- Protagonist Title: The title is the nickname the mobsters tend to stick on Michael Felgate.
- Sadistic Choice: At one point Frank is tasked to kill Michael in order to save Gina.
- Slobs vs. Snobs: The Vitale Family (sans Gina) versus the Cromwell Auction House.