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Jonathan Coulton – Big Bad World One Lyrics 12 years ago
I think what he's singing about is a man that has had trouble in relationships before. He's been hurt or dished out some pain and he doesn't want to go down that road again. Saying that "every time it's going to end the same way" could be taken to mean that he has had relationships before and they don't go well.

"I quit, I'm done" would indicate that he is getting out of the dating scene from which we could infer that he had once been in.

I agree with your supposition about "Me Zero, Big Bad World One" with the addition that he could be admitting final defeat. The world has beaten me, could be the sentiment here.

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