Lots of suggestions, but I have yet to see anyone recommend:
Wishful Thinking (1997)
I know it wasn't loved much by critics and had a pretty low score the for the longest time, but man did this movie hit hard for me way back then. A lot of it is because it so accurately and charmingly captured the sometimes unavoidable jealously, neurotic paranoia, and pathological obsession with the fear of a significant other cheating on you.
I thought James Le Gros did a perfect job playing a psychologically deteriorating jealous boyfriend, while Beals was gorgeous as usual, and Jon Stewart played the unbeknownst smarmy foil to Max's suspicions.
I think the movie only really resonates well if you've been in that kind of situation, and the kind of surrealistic approach to the comedy probably won't be everyone's cup of tea, but it's a movie that tackled relationship woes in ways that few other movies do, or have, since then.
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