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Movies like Break Up 100 (2014)

Sam and Barbara have been together for eight years, but the key to their relationship is breaking up. Each time Barbara threatens to leave, Sam would give in and beg her to come back, giving her an increasing upper hand. After their 99th breakup, the couple finally decides to stick through with their relationship and not break up so easily. They plan a future together by running their own café. Ironically, the success of the café starts driving Sam and Barbara apart, and the 100th breakup between Sam and Barbara seems to be just around the corner.