Melancholy Masochist
noun: a man who constantly subconsciously pursues women who are unattainable or more so not girlfriend material at all. and through this process suffers heartbreak repeatedly due to the combination of lack of self confidence, paranoia, the need to please and on the females part and outstanding combination of mind games, misread-able flirting and leading on. broken at that point the man continues to pursue romance with another similar candidate as the previous as if he enjoyed the pain.
ex: “aww man david likes jane?! he’s such a melancholy m-s-ch-st, she’s gonna f-ck him over just like tina, molly, and sandra did. and then he’s gonna break down and do it again.
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