painaholic
A person who's addicted to feeling emotional pain, doing things such as looking for love in all the wrong places and expecting to find kindness in a wasteland of hatred and despair.
Person 1: Did you hear about how Ryan is trying to get with Amanda, the most popular girl in school?
Person 2: Yeah, everyone knows she rejects anyone and everyone. Poor Ryan, the kid must be a painaholic.
Person 2: Yeah, everyone knows she rejects anyone and everyone. Poor Ryan, the kid must be a painaholic.