It hurts, but it happens. (Think the "Friends" episodes where Ross and Rachel broke up, a misunderstanding occured and Ross ended up having a one-night stand which broke Rachel's heart. The long-standing joke, "We were on a break!" was used by Ross whenever Rachel brought up the issue.)
The problem can really escalate when the estranged lovers get back together. Trust issues can tear apart a relationship if they aren't dealt with properly. If you two are back together, it's important for you to make up your mind whether you're going to trust him and then trust him. But if you feel you'll never be able get over the fact that he dated someone while you were broken up, perhaps you might try figuring out whether the relationship is worth the effort.
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