Now that Brian's father must sell his lake house, Brian invites the gang there one last time for a weekend getaway. He hopes to make Bridget feel more like a part of the group of friends. Meanwhile Dave and Deena grapple with making the decision about their daughter's ear surgery, and Adam tries to figure out his feelings for Heather and Marjorie.
When Brian's Dad decides to take the real estate company away on a retreat, Brian and Bridget gradually get closer. Meanwhile, after Adam and Dave make an awkward visit to the strip club where Heather works, Adam wants his new wife to give up her job; and Nicole promises both Dave and Deena that they can accompany her when she goes into labor -- but neither is willing to give up the spot to the other.
Needing money, Brian starts a job at his father's high-end real estate firm. Sparks fly when he meets the company's top agent, the beautiful Bridget. Meanwhile Dave starts a new job as well, and he and Deena work out a unique child custody arrangement; Adam's relationship with Summer may be problematic for his professional future; and Nicole finds a way to work through her grief after losing her husband.
Serial monogamist Brian O'Hara hits his mid-30s and suddenly realizes he's the last bachelor standing in his circle of friends. Not averse to the happily ever after his friends have achieved, Brian wonders whether he'll ever find Mrs. Right. The fact that he's in love with his best friend's girlfriend doesn't help his chances.