I still don't see why I was wrong to ask "why?" It's not like I said "Why? It'll make you look better!" I like knowing why people choose the things they chose. Hell I even told her as much! I told her I'm asking why because most girls are really into makeup so it surprises me she doesn't have any (I tried clarifying this with her every day for that week she didn't talk to me).
As for the crying incident. All I said was "you've been in the bathroom for an hour putting on makeup, seriously just wash it off." That was my asshole moment, but I felt the follow up made it the most romantic thing a guy could say to his girl. I basically told her the truth, for as long as I had known her (At that point a little over 2 years) she never wore makeup and I didn't understand her need to start, her lack of makeup was one of the things I loved about her and she doesn't need to wear it to appease a bunch of random douche and douchettes who are probably ungodly insecure with themselves. Fuck them, come as you always are and know you're the most beautiful thing in the room.
I mean it was for some event I can't recall something to do with renovation to some building for a charity ball, I don't know we got dragged there by Alyssa. It was faux high society snobbery.