Based on the character Harry Kim from Star Trek: Voyager, the Harry Kim Complex is where a person continuously falls for the wrong person. Despite warnings from friends and family to avoid these people that are obviously wrong for them, they continue to engage in these relationships that are doomed to failure.
"I think Diamond might be the girl for me."
"Dude, Diamond is freaking stripper and from what I hear, she also a whore. I don't mean that figuratively either, I mean she sleeps with guys for money!"
“Whatever dude, she is an angel.”
“Man, you need to go see a therapist and get that Harry Kim Complex taken care of before you end up knocking up one these chicks.”