Head over Heels
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.
Below are the streaming services currently carrying the TV show “Head over Heels” in Canada, along with how each offers it (subscription, buy, or rent) and a direct link. Licensing differs by market, so availability in Canada can differ from other countries.
Where to watch Head over Heels in Canada
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Not currently available on the supported providers in Canada.
Availability can change as licenses rotate — confirm on the provider’s page before subscribing. Last checked: 1 Sept 2026.