I was drunk (very drunk) one night and asked my friend/roommate who had drank only a couple beers if he wanted to hit me in the face. I don't know why but it seemed like a good idea at the time, thinking that he would give me a friendly punch and that would be it. Instead he managed to hit me hard enough to break my jaw in two places which required surgery.
I asked him if he would help with my deductible and he said yes, but since then has changed his mind. Also, after hitting me he said, "You would have called me a p**sy if I hadn't hit you that hard, right?" Does he have any obligation to help with my expenses?
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ANSWER for "Broken Jaw from Getting Punched by a Friend...":
That's a difficult question to answer. On the one hand your friend/roommate clearly assaulted you. On the other hand you invited him to do so. At a minimum your invitation to your friend/roommate to strike you constituted contributory negligence. Contributory negligence lessens the culpability of another.
Your case can also be likened to one in which two boxers are in the ring and one hits the other in the face, breaking his jaw, knocking him down, and winning the fight. Before the fight both men knew they were to be willing participants in a fight. Each man knew he was going to get hit, and hit hard. Neither of them thought he would be hit in the face hard enough to suffer a broken jaw.
It would be a fair statement to say the fighter whose jaw was broken thought he was strong enough to withstand at least one blow to his face. Otherwise he wouldn't have climbed into the ring.
The same can be said about you. Intoxicated or not when you asked your friend/roommate to hit you in the face you did so because you believed you were tough enough to withstand a punch to the face. Surely you didn't believe you would suffer a broken jaw. If had you surely wouldn't have agreed to allow the other man to strike you.
You really don't have much of a case. There is in our society a mechanism which can be employed to avoid invitations to others to commit assault against you. That mechanism is called sobriety.
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