Lisa convinces Rebecca to try a one-night stand. Meanwhile, Perry takes a stay-at-home vacation, which irritates unemployed roommate Shawn so much that Shawn is willing to take a job---virtually any job.
Rebecca and Perry attend their high-school reunion, where a prom-night humiliation haunts Rebecca. Meanwhile, Shawn romances Lisa's friend Vanessa because her cable system carries the hockey championship games and his system doesn't.
Rebecca meddles in Lisa's love life, and Lisa finds a way to get payback. Meanwhile, a pretty girl short-circuits Shawn's attempt to pick up roommate Perry after gum surgery, and Perry kicks him out of the apartment.
In the opener of this ensemble comedy about four friends' hapless love lives, Perry (Kyle Bornheimer) has a problem with bedroom banter, and Rebecca (Alyssa Milano) rushes into romance when she learns that her ex is remarrying.
Rebecca sees potential in her date---until she sees the tattoo on his chest. Meanwhile, Perry tries to fire his assistant (Anna Camp) but unwillingly winds up in a relationship with her instead; and Shawn is reluctant to dog-sit for a coworker before he learns that the pooch is a babe magnet.