After Shelly meets Jack's intelligent, witty new girlfriend, Brian wonders about her true feelings for her former boyfriend.

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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 Brian'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 Brian's own set of betrayal.