A comedic triangle involving two best friends (Tim Conlon, Paul Stephen Rudd) and the teacher (Paula Marshall) one of them used to date. In the opener, womanizer Jack learns that he still harbors feelings for his ex after roommate Brian asks for her phone number.
After two weeks of blissful dating, Shelly and Brain's feelings for each other are tested by the reappearance of a man from Shelly's past.
Jack fumbles an attempt to improve his image when his promise to treat his friends to a sold-out football game is sidelined by his need to score with a beautiful woman.
When a local TV show films the friends' interaction, Jack plays to the camera and violates Shelly's request for privacy, leading to Brains own set of betrayal.
After Shelly meets Jack's intelligent, witty new girlfriend, Brian wonders about her true feelings for her former boyfriend.
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