Jack (Andrew McCarthy) is an executive in a financial brokerage firm trying to impress the firm's 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.