Painting contractor Gary (Jay Mohr) and his ex-wife (Paula Marshall) navigate kids and new relationships in this comedy, which opens with Allison announcing she is remarrying and Gary getting involved with a client who isn't convinced that he's ready to start dating again.
When Gary disrobes in front of Allison they realize they're still too familiar with one another. Determined to put some distance between each other, they set up new ground rules for their postdivorce interactions.
Allison and Vanessa's growing friendship is making Gary nervous because of its potential to color Vanessa's impression of him. To stave off any embarrassing revelations, Gary urges the women in his life to look elsewhere for female bonding.
Gary tries to outdo Allison when he learns she is taking the kids to their first concert. He counters by planning to share significant life events with them such as helping Tom with his first shave and purchasing Louise her first bra.
Gary plays host to his half brother, Mitch (Rob Riggle), who has returned from the war and needs a place to stay. Gary's full house soon spins out of control, and he finds himself in the role of parent to both his sibling and his kids.