Plot
Against the advice of his best friend Ted, Anderson proposes in a crowded restaurant to his girlfriend Vanessa, while dressed in a cupid costume. The shock of the unexpected proposal leads to her fatal heart attack.
Utterly devastated and distraught, Anderson quits his job and goes into mourning. A year later, he is still obsessed with his perfect (and deceased) former girlfriend. While Ted and Anderson are having lunch together in a diner, Ted points out he's been in mourning for longer than they were actually together. To help him move on, Ted persuades him to give romance one more try. To placate his friend, Anderson agrees, looks around, and asks attractive waitress Katie to marry him. To both men's utter astonishment, she accepts his proposal.
Katie had a flashback to the previous evening, when she, her boyfriend William, her mother Lois and stepfather Stuart were playing charades. He has her guess 'Will you marry me' and she isn't sure, so she visits her imprisoned dad Smitty for advice, which is, listen to your heart. So, when she arrives at work, she tells her friends she's going to accept William. Directly afterwards she walks into the dining area and the Anderson proposal happens.
Anderson and Katie go for a walk, warming up to each other. She tells him her parents had a shotgun wedding in The House of Wedded Bliss in Atlantic City. Before they realize what's happening, Katie proposes to him and he accepts.
The same day she moves into his apartment, which they call taking things slow. He rigorously cleans his apartment while she rushes to her parents' to pack her bags. Katie's friend Matador drives her to Anderson's apartment and accidentally hits him. Temporarily knocked unconscious, Anderson talks to Vanessa. He promises her to be ever faithful. However, when he wakes up he goes ahead with plans to meet Katie's parents, and brings Katie to meet his.
At Katie's mom's and stepdad's house, Anderson proves to be terrible at charades. But trying to bond with her dad he goes to see his Jewish toy workshop, while Katie comes face to face with William. He's been there spying, and he desperately wants her back.
At Anderson's parents' house, things are also awkward. While his dad takes him for a walk and pep talk, his mother tells Katie she blames Anderson for the death of her would have been daughter-in-law Vanessa.
Meanwhile, Smitty breaks out of jail to walk Katie down the aisle. He arrives at ex-wife Lois's house and through their long lost passion for one another, their love sparks again, much to Stuart's discomfort.
After an argument over Vanessa, who Anderson hadn't told Katie about although he'd had opportunities to do so, their relationship is on the rocks. She comes by the apartment, angrily demanding her things, and they finally declare their mutual affection.
Anderson, Katie, Ted, and the rest of the party drive to Atlantic City in a car from the car dealership where Ted works (under the pretense of test driving the vehicle). William proceeds to assault Anderson at a rest area outside of Atlantic City. Ted's boss reports the car stolen, and a nervous Ted crashes into a police car, resulting in their arrest.
Meanwhile, Katie's parents know where they're headed and follow, stopping to rob the Tuxedo Depot in preparation for the wedding, and are subsequently arrested. They all end up in the same police station, and Anderson's parents also turn up after he calls them. Katie's parents trick the two cops on duty so the group is able to escape from the station after taking an officer's gun and locking them in a cell.
At this point Anderson and Katie reestablish that they want to get married, and for the first time the whole group is in favor. Now in a police van, which the policemen let them use, they drive to Atlantic City and Anderson and Katie finally get married. However, as soon as they step outside they are all arrested. Anderson and Katie spend their honeymoon in jail.
