Sure Bet (1996)

The sexual misadventures of three buddies with one bet: which one can seduce a famous porn star. Their task is much more difficult than any of them had imagined, as the most unusual obstacles get in their way. Danny, one of the three, is arrested while trying to break into a house, and has all but given up hope. But in a final stroke of luck, he finds himself in community service on the street where she lives. She gets a thrill out of teasing him, but will she go the distance?

Unfortunately the movie Sure Bet is not yet available on HBO Max.