Tom, greeting-card writer and hopeless romantic, is caught completely off-guard when his girlfriend, Summer, suddenly dumps him. He reflects on their 500 days together to try to figure out where their love affair went sour, and in doing so, Tom rediscovers his true passions in life.

A pair of high school sweethearts, Grace (Rena Sofer) and Michael (Dean McDermott) are reunited after 20 years apart at their school reunion. Sparks fly as the two catch up but it’s not that simple as Grace is taken by safe, reliable Philip and she’s determined to do the right thing. Also in the way is Grace’s well meaning but meddling mom Mary (Barbara Eden) who also believes her daughter should be with Phillip. Will true love win or will their second chance go up in flames?

A budding romance between noble underachiever Lloyd Dobler and high school valedictorian Diane Court is threatened when Diane’s overly possessive, disapproving father interferes with their relationship. With a prized scholarship to study abroad hanging in the balance, Diane must find a way to make both men happy.