The group finds out about the shocking marriage of Adam and Heather, while the newlyweds try to decide if they did the right thing. As a way for Brian to forge a romantic connection with a reluctant Bridget, Dave suggests that he get her to participate with them in a speed dating event at Ivy's bar. Meanwhile, Nicole immerses herself in Deena's fledgling cupcake business to distract her from her grief, and Deena meets a rich client who might take more than just a business interest in her.

Brian and his dad, Michael, start to connect, until a secret involving Bridget drives them apart again. When Adam has trouble adjusting to Heather's ongoing job as a stripper, Jimmy runs a criminal record check on her. After a couple of "practice dates," Deena decides to go for the real thing with the wealthy T.K., her first cupcake client. Meanwhile, Dave goes along with Nicole for moral support to a screening of Angelo's last movie, where she meets a mysterious woman with a connection to her late husband.

Brian tries to stay away from Bridget once he learns that she and his father once had an affair, but she's not making it easy. For comfort, he considers reconnecting with his mother, whom he hasn't seen in a while. Meanwhile, Brian and Adam are sentenced to community service at a homeless shelter to pay for the damage they caused at Ivy's bar; the very pregnant Nicole goes to some humorous extremes to induce labor; Deena goes on a dream date with her rich client, and Dave goes on a date with a much younger girl.

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.