"However, he's still planning on going to Retro, so it's weird.. either he doesn't want to "hurt" me or he wants to look like he tried everything."
That's exactly why he's going. It's to clear HIS conscience not to soothe you. He's going so he can tell his buddies "hey I did everything I could".
It's why you should bust up his little fantasy beforehand. Besides R won't work if he's not honest. Stand firm and confront him about the OW. It doesn't have to be the full blown intervention, but talking to him calmly yet firmly to show your strength and resolve is what's going to help.
M-43 W-40 2D - 9 and 5
Emotion, yet peace. Ignorance, yet knowledge. Passion, yet serenity. Chaos, yet harmony. Death, yet a new life.
