Holly attends her ex-boyfriend Paul's wedding and throws it into chaos. At the wedding Phil and Eden realize they're developing feelings for each other. Haskell sets his sights on the most desperate woman at the wedding.
Phil's client, tennis star Chuck Feeney, stays with the guys to hide from the paparazzi. But Chuck the ladies' man turns out to be more of a man's man. Haskell and Holly compete over who can take better care of pregnant Eden.
Holly dates a much younger man and Eden questions his motives. Phil and Eden secretly become friends with benefits. Stuart convinces Haskell to pursue a woman he's admired from afar and ends up accidentally stealing her cat.
Haskell's ex-wife Margo gets amnesia after an accident and stays with Haskell to recover, only she thinks they're still married. Phil and Stuart spend the night in Holly's place and get to know her intimate sleeping behavior.
When Holly despairs about dating again, the guys secretly create an online dating profile for her and discover what dating is like from a woman's perspective.
Desperate to impress her perfect sister Jill, Holly invents an alternative lifestyle for herself that quickly spirals out of control. Meanwhile, the guys are riding high on a "special" dish cooked up by Stuart.
Holly volunteers to help Stuart impress his ex at a ballroom dance competition, but Holly's "talent" hurts more than it helps. Phil meets his match in a woman who beats him at his own game.