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).

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.

Set in Miami Beach,[1] the series is about the Head over Heels video dating agency, operated by brothers Jack and Warren Baldwin (Peter Dobson and Mitchell Whitfield, respectively).

[3] The bisexual, celibate Ian is frequently questioned about his sexuality,[1][2] and former stripper Valentina (Cindy Ambuehl) is a receptionist who is knowledgeable about computers.

[8] The pilot episode features Warren having sex with a client in his office despite the agency's dating policy,[3] and a bikini fashion show.

[2][12] Storylines in other episodes include Jack using Cap'n Crunch as an alias in chat rooms to seduce women and Valentina saying she would open the mail topless for $1,000 a week.

[16] Sociologist Suzanna Danuta Walters wrote that Ian and Josh Nicolé Blair (in the sitcom Veronica's Closet) represented a trend in which "homosexuality is a running gag", and characters were in denial about their sexuality.

[36] Citing it as one of the season's worst half-hour shows, the Rocky Mountain News's Dusty Saunders described Head over Heels as an unsuccessful attempt to emulate Friends.

[3][5] Despite calling the show a miss for UPN, Tom Shales wrote that its humor was not as "ugly and vicious" as the sitcom Hitz; he also praised Patrick Bristow's scene stealer and Valentina's technological aptitude as "a cute touch".

[5] The opening titles received praise from Adam Sandler of Variety, who described it as "stylish and provocative" and comparable to those for the crime drama Silk Stalkings.

[6][7] David Zurawik of The Baltimore Sun singled out Valentina and the Baldwins' mother as examples of the series's poor representation of women.