It's not that big of a deal. But, what I'm trying to show you is the other side. Being around an egg-shell walker is torturous too. "Oh my God, she's so skittish, can't I ever just relax without making her nervous?" Being around someone constantly assuming one's feelings and trying to manage them is stifling. My point is that he didn't ever have a chance to form his own feelings/reaction -- you handed them to him preconceived.
IMAGINE he wasn't judging you and condemning you from the moment he walked into the door. IMAGINE he might have actually gotten something positive fun it. You didn't really give him space to have such an experience without feeling stupid or embarrassed about it.
Did you ever have a friend who was constantly shaping herself to be congenial to you, changing her favorite color, her food, never saying what she wanted to do, soooo worried about turning you off? Not much of a friend really because that other person really isn't in the R, but instead some kind of warped reflection of you.
Imagine you are a size 16/18 and a friend takes you shopping to a non-plus sized store. You wonder if anything might fit, you see an amazing outfit you think might work, it is fun to be shopping with your friend. But then she pulls you over and says, "Mish, I'm so mortified they only have regular sized clothes here, I'm so sorry for bringing you, I didn't know." HOW WOULD YOU FEEL?
Be who YOU are. Be direct. STOP managing Gabe -- let him be who he is.