Head over Heels is an American television sitcom created by Jeff Franklin that aired on United Paramount Network (UPN) from August 26 to October 28, 1997. It is set in the eponymous video dating agency based in Miami Beach, Florida, run by brothers Jack and Warren Baldwin (played by Peter Dobson and Mitchell Whitfield, respectively). The remainder of the cast consists of their employees, played by Eva LaRue, Patrick Bristow, and Cindy Ambuehl. Connie Stevens was initially cast as the Baldwins' mother, but never appeared in the show after the pilot was rewritten. Andrew Gottlieb was a co-producer, and Vince Cheung and Ben Montanio were consulting producers.

The sitcom was the lowest-performing series tracked by Nielsen Holdings for the 1997–1998 television season. Since UPN primarily marketed its programming to African American audiences, critics questioned the show's lack of a black main character. With its inclusion of Ian, Head over Heels was one of 30 U.S. programs to feature a gay, lesbian or bisexual character that television season. It received a negative response from commentators, who criticized its sex comedy and characters.