TV Head over Heels Head over Heels 8/10 by 1 users Head over Heels is a 1997 TV series, that aired briefly on UPN. Jack and Warren Baldwin are two brothers who take over the operation of "Head over Heels", a South Beach, Florida video dating service founded by their mother. The staff at Head over Heels includes Ian who produces each client's video, and Valentina the receptionist. Details Casts Posters Images Title Head over Heels Alternative Titles First Air Date 1997-08-26 Last Air Date 1997-10-28 Number of Episodes 10 Number of Seasons 1 Genres Comedy, Networks UPN, Casts Mitchell Whitfield, Patrick Bristow, Eva LaRue, Cindy Ambuehl, Peter Dobson, Kevin Farley, Heidi Mark, Morgan Fairchild Plot Keywords , Mitchell Whitfield Patrick Bristow Eva LaRue Cindy Ambuehl Peter Dobson Kevin Farley Heidi Mark Mona DuBois Morgan Fairchild