I say go for it! He's not going to be weirded out by you starting a conversation with him. I've personally never known of a guy who felt that a woman pursuing them first was weird.
What have you got to lose? If he's too shy to approach you and neither of you ever talk to each other, you will definitely not have your chance then, so take your shot while you have the chance!
Have any of you girls approached a boy first?
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I say go for it! He's not going to be weirded out by you starting a conversation with him. I've personally never known of a guy who felt that a woman pursuing them first was weird.
What have you got to lose? If he's too shy to approach you and neither of you ever talk to each other, you will definitely not have your chance then, so take your shot while you have the chance!