I'd say he might like you, and wants to see what you think about him.. or he could just be an egotistical jerk looking for a boost.. it really depends on the guy.. 5 different guys could ask that and it could mean something completely different to each of them..
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he just wants to boost his ego. he probably thinks he looks good (and he might actually) but to have a girl confirm will make his day. he's not insecure...just annoying
I have a friend exactly like this. A player, who claims to be looking for that special girl. He is pretty much trying to boost his ego and also flirt with you.
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