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It wasn't particularly messy or anything like this, but it's still my worst breakup in terms of how crappy/depressed/bad I felt afterwards:
We had been going out for 5 months, and it's going absolutely wonderfully. She did and said several things that showed that we were really something special, something more than her many past relationships (and I still believe she was speaking the truth)... To name a few, 3 weeks into the relationship, she tells me in (happy) tears that she wants to stay together when she goes to a 9 month study abroad program 6 months down the road... or that she ignored personal "limits" she would impose on herself in past relationships because she thought our relationship was that good...
So 5 months in, things are going absolutely great, and she tells me, completely out of the blue, she has unresolved feelings for an ex boyfriend, who she had gone out with some 2+ years ago, and the 2 months they had gone out were a complete disaster, but still she had these unresolved feelings..... so she breaks up with me.... and I'm left thinking wtf...
Ok, not as bad or messy as some others, but damn i had to get that off my chest....
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