Head Over Heels

Season 1

TV-14

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.

Where to Watch Season 1

10 Episodes

One Down
E1
One DownWarren thinks Jack's raucous social life is interfering with business, so he institutes a new policy prohibiting agency employees from dating clients. But when Warren's new girlfriend unceremoniously dumps him, he is suddenly inclined to break his own rules.
Gigolo Guy
E2
Gigolo GuyIan's macho twin brother Kevin arrives to make trouble in South Beach while Jack falls prey to Mona, the demanding owner of a photo studio, who has both a penchant for John Travolta and some unusual plans for Jack.
Game Show Guy
E3
Game Show GuyA TV station executive suggests Warren create a dating-game show.
Vice Guy
E4
Vice GuyAfter Jack is ridiculed by the staff for his lascivious behavior, he gets even by persuading his co-workers to stay away from their own vices for a whole week.
Witness Guy
E5
Witness GuyWarren and Jack post their client's picture on their website, only to discover that the man is a member of the government's witness protection program.
Hot Guy
E6
Hot GuyA sexy client sparks rivalry between Valentina and Carmen, who are both determined to win him over. Meanwhile, Warren's former fiancÃ©e shows up at the agency hoping to seduce him.
Spider Guy
E7
Spider GuyJack works to find a match for Valentina's raunchy grandmother Lola in a nearby seniors home after Warren is hospitalized by a spider bite and Jack is left running the agency by himself.
Reunion Guy
E8
Reunion GuyWarren and Jack resolve to attend their high-school reunion determined to prove that they're both successful, desirable men.
Pilot
E9
Pilot
Drag Guy
E10
Drag Guy