Jack (Andrew McCarthy) is an executive in a financial brokerage firm trying to impress the firms president, Drew Clayton (Chris Gillett), in hopes of a promotion. However, Jack is dating the fabulously rich and elegant Demi Clayton (Stephanie Mills), who happens to be Drew's daughter. Although Demi's mother Clarisse (Jane Moffat) doesn't necessarily approve of Jack and would prefer her daughter to date a man within their social circle, Jack still plans on proposing. Trying to create the perfect proposal, Jack signs up for dance lessons in preparation for his proposal to Demi at her father's lavish annual Christmas Dance. But when sparks start to fly between Jack and his dance instructor, Christine (Michelle Nolden), Jack will have to make some important decisions before it is too late...