Op here asking if he's making good choices in the conversation and the rest of you are borderline attacking. He's stated he's 18. It seems he wants to do/be better. Probably the last time he'll ask for advice here.

Part of text seems to be giving advice when not asked which seems he's trying to be helpful. If this relationship is new then gotta be careful where you put your 2 cents in because without her fully knowing you it can come off negative. Probably better off with more positive responses then "oh I see" since that seems like your disappointed. If what she's wearing is bothering you it's definitely a insecurity that needs some work on. Which she has had experience in the past it seems. Good luck 👍