How do Immature/Younger Guys Flirt?

So, this guy who has asked me out before (seriously) a year ago was like "You're sexy." then "You're really pretty" as he passed me in the stairs for some random reason - we haven't spoken for ages, and this isn't the first time this has happened, a guy in my English a while ago was like "You're beautiful" and a few other guys have done this thing of calling me pet names etc. and it bugs me because I don't know if they're trying to make fun of me or are genuinely attracted me.

Basically, if you were a younger guy (teen years) if you came up to girls randomly and said they were hot etc. would you do it as a wind up or do it because you thought they were good looking?

Also, I'm not the most popular girl, but I've been asked out a few times and I'm pretty sure I'm not ugly, I get called pretty quite a bit by friends.
How do Immature/Younger Guys Flirt?
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