Joy's fun and beautiful new friend Eileen also happens to be Eddie's ex-girlfriend. At first, the friendship doesn't seem to be a problem until Joy invites Eileen over to the house and Eddie gets himself in trouble by reminiscing a little too fondly about the past. Meanwhile, Kenny thinks he's doing something nice for his new girlfriend by babysitting her kids, but doesn't realize she may be using him.

When Joy urges Eddie to get a check-up from their doctor, Simona (Susan Yeagley), Eddie becomes enamored with her and her husband, Stephen (Kevin Nealon), and their seemingly perfect life. Joy becomes annoyed when Eddie becomes ardent about taking Simona's advice, even though Joy has been nagging him for years, and decides to prove to Eddie that Simona isn't as perfect as she seems.

When Allison's boyfriend Doug is hospitalized, she rushes to his bedside only to be surprised with a proposal. No one is more surprised by their daughter's engagement than Eddie and Joy who plot to put the brakes on wedding planning. Meanwhile, Kenny tries to get Eddie's car repaired without success.

When Joy and Eddie experiment with role-playing to spice up their love life, they realize that pretending to be someone else isn't as sexy as being themselves. Meanwhile, to supplement his income, Kenny tries finding lost dogs to collect the reward money.