In need of money, Brian starts working at his father's high-end real estate firm. Sparks fly when he meets the company's top agent, the beautiful Bridget. Meanwhile Dave begins a new job as well, and he and Deena work out a unique child custody arrangement; Adam's relationship with Summer may mean problems with his professional future; and Nicole moves on despite the grief after losing her husband.
Brian is the guy everyone wants as a best friend. He's the guy who'll stand by you at your wedding, drive you to the hospital, cheer your kids on at their little league game... the guy who every wife dotes on and every husband wants to either grab a beer with or live vicariously through him. But as all of his friends pair off and Brian emerges as the last bachelor standing, questions begin to arise in his head: Is there such a thing as Miss Right? Why does love have to be so complicated? What is his problem with commitment? And the most pressing question of all, could all of his problems stem from the fact that he is harboring a crush on his best friend's girl?
At 34, Brian is the last single guy in his group of friends: his best friend Adam was going to break up with picture-perfect Marjorie but proposed instead. Brian's sister, Nic, and her boy-toy husband, Angelo, are trying hard to have kids. The bohemian Dave and Deena have three little girls and no sex life. And, like all married people, they can't wait for Brian to join their "club", though they're not exactly sure why. As for Brian, well, he's a serial monogamist but still holds out hope that one day he'll open the door and be blinded by love.