Tom and Jessie announce their engagement, throwing their families into chaos.

Tom and Jessie's attempt to find a place of their own backfires disastrously.

Jessie makes an ill-fated stab at winning Judith over at her belated bridal shower; while Tom gets roped into letting the dads crash his bachelor party.

Tom's manhood is tested when Jessie tries to teach him to drive.

Jessie and Tom enter the dangerous waters of the joint bank account; Judith tries to hone in on Tara's exercise regime.

A secret from Ben's past threatens to ignite over a family dinner with a rabbi.

Tom discovers that parental endorsement does nothing for his sex life.

Tom and Phil team up in an ill-fated business scheme; Jessie gets in over her head when helping Judith re-design her kitchen.

The parents get trapped in Phil's garage with unresolved tensions and hash brownies; Tom and Jessie duel in the kitchen over what to serve their parents for dinner.

Judith and Jessie compete to look after Tom when he gets a cold; Ben is horrified to learn Phil is in Mensa; Tara deals with an irate mailman.

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.