Life as a married man can be all-consuming: arguments, in-laws, make-up sex, normal sex. Luckily Tom has a friend like Carter to remind him that he's still eighteen. So, at Carter's insistence, Tom accompanies him to a campus party for some innocent fun. Innocent, that is, until Carter spots his dream girl and asks Tom to distract her friend by being his Wing Man... his unwed, available Wing Man. With no pressure to hook up, Tom finds it easier to talk to the girl, even tell her things he can't say to Jessie. What's the worst that can happen? The hot girl you're pretending to be interested in wants to have sex? You run off and accidently forget your cellphone? Or your wife calls said cell phone and finds out about the whole thing? Meanwhile Jessie gets a peek into Monica's Sex-In-The-City lifestyle when she helps her design her new pad. The Poster Girl for the Single Life starts to rub off on Jessie. One night at the club, Jessie gets carried away and ends up losing Tom's ring. Now Tom and Jessie both have secrets, and their marriage is about to face its toughest test yet.