I think it's about how he made a mistake or screwed up with this girl, and she has dumped him, but he thinks there is a chance they might get back together which is why he's saying he doesn't care less about the pain and that it will be worth it when they do.
I think it's about how he made a mistake or screwed up with this girl, and she has dumped him, but he thinks there is a chance they might get back together which is why he's saying he doesn't care less about the pain and that it will be worth it when they do.