Smart and beautiful Rebecca is recently divorced after 15 years of marriage. Having never really dated before she was married - and not having been on a date since Clinton was in office -- she finds it scary to start over now. Although a gifted mom and lawyer, she is clueless about dating and hopes to get some help from her equally romantically challenged friends.
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.
When it's time for Rebecca and Perry to go back to their high school reunion, Rebecca is ready to confront Jesse, the guy who publicly humiliated her by standing her up at the senior prom. But Perry knows the real reason why she was stood up and tells a preposterous lie to keep Rebecca from discovering the truth. Meanwhile, avid hockey fan Shawn is devastated when he finds out that the local cable company won't be carrying the championship games. When he learns further that Lisa's friend, Vanessa, has the games on her cable station, he has to hide his real motive for romancing Vanessa from both women.
Although Rebecca said she wouldn't meddle in sister Lisa's love life, she can't resist finding out why Lisa would break up with "nice guy" Neil. When Lisa finds out what Rebecca did, she finds a way to get back at her. Meanwhile, as Shawn is on his way to pick up Perry from his dental surgery, he gets distracted by a pretty girl, proving once again that the ladies come first in his life, so a fed-up Perry kicks Shawn out of the apartment and refuses to forgive his BFF.
After Rebecca learns about her ex-husband's impending wedding, she decides to jump headfirst into the dating pool. But the crew get her so worked up that, when it comes time to the actual date, she becomes flustered and ends up saying some ridiculous things about herself. Meanwhile Perry meets a girl he thinks is perfect - until he finds out she likes to be talked dirty to during their romantic encounters, so Lisa takes it upon herself to coach Perry through Dirty Talk 101; and Rebecca enlists struggling and unpublished writer Shawn to help her son, Justin, write a story for his high school English class.