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This means either he likes you or he is the biggest flirt alive. If you were alone- he likes you but if you were in a group- FLIRT!
write and wrong it depends on the guy if he's a sweet guy then he might mention it and help you I mean I would it's just a nice thing to do but ask him don't be afraid guys are like Zombies if your beautiful then you can do anything and it won't look stupid to guys. Mostly because there staring at your boobs. Hahaha anyway hope this helps.
I think it just means he is a nice guy who wants you to look your best.
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