There was a movie (not too sure if it came out in the 90s or early 2000s. It was on HBO though) about a man who is able to either go back in time or relive the moment. He was cheating on his significant other but then regretted it when he saw the pain it caused her after she finds out. So he either goes back in time, able to relive the moment, and stops cheating on his significant other. The problem though is that though he does not cheat on his wife/girlfriend/significant other she ends up cheating on him. Does anybody have an idea what movie this could be?
Might this be The Man with Rain in His Shoes AKA Twice Upon a Yesterday (1998)...?
Victor (Henshall) is an actor in London who is desperate to stop his ex-girlfriend, Sylvia (Headey), to whom he was unfaithful, from marrying another man. After meeting two mysterious dustmen, he is given the chance to travel back in time and relive his romance. However, he finds that things develop differently this time around—Sylvia has an affair with Dave (Strong), and she leaves him.