Deal of a Lifetime is a 1999 US romantic comedy

Romantic comedy film

Romantic comedy films are films with light-hearted, humorous plotlines, centered on romantic ideals such as that true love is able to surmount most obstacles. One dictionary definition is "a funny movie, play, or television program about a love story that ends happily"...

 film

Film

A film, also called a movie or motion picture, is a series of still or moving images. It is produced by recording photographic images with cameras, or by creating images using animation techniques or visual effects...

 starring Shiri Appleby

Shiri Appleby

Shiri Freda Appleby is an American film and television actress. She is best known for her leading role as Liz Parker in the television series Roswell...

, Michael A. Goorjian

Michael A. Goorjian

Michael Antranig Goorjian is an American actor and filmmaker.-Early life:Goorjian was born and raised in Oakland, California. He has been singing, acting, directing, and choreographing since he was in junior high school...

, and Kevin Pollak

Kevin Pollak

Kevin Elliot Pollak is an American actor, impressionist, game show host, and comedian. He started performing stand-up comedy at the age of 10 and touring professionally at the age of 20...

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The film centers around the main character Henry Spooner (played by Michael A. Goorjian), the school nerd who has a crush on Lori, the prettiest, most popular girl in his high school. After a conversation with his friend he mutters under his breath that he would sell his soul to the Devil to go out with Lori. From that point on, he gets his wish to date Lori, but things don't go according to plan.