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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?

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    Ted Chiang's short story "The Merchant and the Alchemist" has some similar-sounding themes, although it was published in 2007, and was not an HBO production. – Lexible Apr 26 at 1:24
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    I haven't seen the movie adaptation of The Time-Traveller's Wife, but it's about the right time and they may have garbled the novel enough to match this. – Spencer Apr 26 at 1:41
  • @Lexible Wow that's an interesting story but that's not it. Appreciate that though. – יהודה Apr 26 at 1:49
  • @Spencer I appreciate the response but that's not it. There were no children involved and the protagonist (or viewers) comes to the realization that they two cannot or were never meant to be with one another. – יהודה Apr 26 at 1:52
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    Yep. That's why I left a comment, and not an answer. :) By the way, welcome to SFF, @יהודה – Lexible Apr 26 at 16:19
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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.

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