Should he confront her after all of this?

this is the kind of dumb crap two socially backwards children do on the playground. and get real, your job in life is not to monitor or get involved in his own stupidity. you sound like some soap opera, take care of you, find some girl you like that is not some 51 50 basket case who with the help of your friend had to have the dean tell you what to do. We all live and learn from out mistakes the definition of insanity is doing the same thing over and over again expecting different results. (look it up)