One key (and obvious) thing that most people missed is why is this smooth talking, supposed know-it-all "ladies man" hanging out with a wimpy, dork loser ("loser" in the traditional high-school sense). Other than Mark, you never see Damone hanging out with friends, he always seems to be alone. When Mark is out on his date, which we can only assume it's a weekend night, instead of being out with buddies, a girl, or out chasing tail, Damone is in his room eating and watching tv.
So it's like Damone clinged on to the first person who respected and admired him. Someone who thought he was more experienced and bigger than he really was. On the plus side, it did seem Damone was genuinely interested in helping his buddy out, and did feel guilty for what he did. Since he probably never really had those experiences before, it was hard for him to deny and he just buckled under pressure.
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