Dave is surprised to see that his new boss, Natasha, turns out to be his former intern. She has re-invented herself from being overweight and non-descript into a sexy, manipulative and shrewd businesswoman. While Bridget is away on a business trip, Brian's downstairs neighbors, Laura and Stephanie, convince him to let them use his apartment for a party that turns raucous. Meanwhile, the still-celibate Adam continues to pursue his law partnership, Dave moves into the guest room back home and Nicole has an erotic dream about her "manny".
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.