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A 35-year old guy who got married right out of college finds himself newly divorced and ill-prepared to re-enter the dating scene.
Avoiding the signing of his divorce papers, Jack "Gator" Gately realizes that he is ill-prepared to re-enter the dating scene. While getting lucky with one date, her monkey goes "bananas" for Gator.
Gator's perfect new girlfriend has one minor physical flaw. She has a skin tag on her back, and Gator just can't get past it. He enlists Tommy to take drastic measures and slice it off her. Yet when Gator learns that the flap of skin reminds the girl of her dead mother, he tries to stop Tommy but it's too late.
When Gator and Freddy meet two attractive Icelandic nannies, Freddy begs him to let them partake in what can only be imagined in beer commercials. So Gator agrees, but begins to relive his college drinking and glory days by getting completely wasted. Freddy is forced to take him to the hospital to get his stomach pumped. Yet the doctor on call is Kate's friend Gabby who Gator had hoped to date. Gabby is not impressed by Gator's childish, partying ways.
Gator joins Kate's boxing gym only to be challenged by a woman in the ring. Kate confronts a co-worker who has no problem being naked in the locker room. However, Kate has a problem with her nudity. Freddy teaches Tommy the art of tantric sex methods.
When Gator is guilt-forced to hire a new assistant that is handicapped, he is reluctant to fire the guy who turns out to be a jerk. Despite Gator's description, Kate starts dating the guy. Tommy finds love at jury duty with the convicted. And Freddy calls a helpline and ends up reconnecting with his ex-wife.
Gator woos his new neighbor by pretending to be an animal-rights activist even though he's a proud meat-eater. Kate decides to not be so picky when she dates an exterminator. Tommy teaches Freddy how to drive.
