Charming and acerbic, Gary hasn't dated since the split, but finally connects with Vanessa, a single mother whose condo he was hired to paint. He dreads telling Allison about Vanessa because it doesn't adhere to her belief in their marriage counselor's book, "Rules for the Perfect Divorce." However, when Allison tells him that she's engaged to their shrink, all bets are off and Gary decides it's time to move forward. Now, in pursuit of post-marriage happiness, Gary must juggle his eclectic world of an ex-wife, their two kids, their shrink, and his gorgeous new girlfriend.