When you feel confident! If you guy's are close, than just go for it! Because chances are he/she will talk to you just as you always would! But if you guys are NOT very close, my best advice to you would be to take it slow, but kinda hint that you like them! You dont want to be all over them because that might not go as well as you would want! But just flirt a little bit! Say "Hey I like your shirt today!" Or "Hey, nice hair!" The key is to not over do it!
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