Eddie becomes distraught when Wendi breaks up with him over disagreements on how they want to handle their future. Meanwhile, Mike struggles to address Eddie's heartbreak, and Peggy contemplates whether she has to break up with Wendi too. To complicate things further, Joey convinces Frank to send Wendi a love letter, pleading his case as to why she should be his girlfriend. With Frank's impending humiliation on the horizon, the Cleary boys try to help him retrieve the letter and just end up getting into more trouble.

To inspire Timmy to take better care of his personal hygiene, Peggy decides to take matters into her own hands and tricks him in hopes of solving the problem. Meanwhile, a concerned Mike fears that Peggy's meddling is causing Timmy to develop insecurities and robbing him of his passion for performance. At school, Timmy receives a Valentine's Day card from a secret admirer and becomes unnerved by the possibility of having a mystery suitor. Elsewhere, Eddie reports a recurring incident to Wendi's boss in an attempt to be helpful, but his chivalrous deed backfires.