While preparing for the wedding, Annie realizes that Jake needs more groomsmen to match her nine bridesmaids and makes a concerted effort to reunite Jake with his long lost friends. Once "The Boyz" are back in their lives however, Annie finds herself competing with them over who knows Jake the best. She also learns that Daniel may be the real reason behind Jake's falling out with his friends. Meanwhile, Gil persuades Dennah to join him in his newest business venture - diet shakes.

When Jake becomes exasperated with a few of Annie's quirky habits, he enlists Kay to gently make some adjustments to her behavior. In return, Jake helps Kay plan an awesome Valentine's Day celebration for her new girlfriend Hailey. When Annie realizes the game, she quickly turns the tables, enlisting Kay to amend some of Jake's annoying behavior. Meanwhile, when Gil gets hurt at the Kevin's annual President's Day party, he and Dennah become smitten with the firefighters who respond to their 911 call and then become obsessed with finding them again.