Rebecca wants to take her relationship to the next level with a seemingly normal guy, but reconsiders when she discovers a giant tattoo of a scantily-clad woman on his chest. Meanwhile, Perry's struggle to fire his enthusiastic but lousy assistant, Erin -- who incorrectly anticipates his every need -- lands him in an unwanted relationship with her; and Shawn is reluctant to watch Lisa's coworker's cute dog until he realizes what a great chick magnet the little guy is.

Lisa finally convinces Rebecca to have her first one night stand. But the always polite Rebecca violates Lisa's number-one rule by calling her date, Leo, the morning after. Now Leo is into Rebecca, so Lisa gives her sister her own unusual brand of dating advice so Rebecca can break up with him. Meanwhile, an overworked Perry decides to take a stay-cation. But doing so gets on the nerves of his unemployed roommate, Shawn, to the point that Shawn decides to get a job - any job.