u No it means he has struggled with that part of dating a girl. I take it to mean he is just not good at flirting or talking to girls and it has tanked previous potential relationships. Means nothing about being still caught up or hung up on a last girlfriend or someone he dated. To be safe though just ask him what he meant by it. He obviously is willing to share that weak spot of his with you so go ahead and ask him to clarify. Can't hurt.
No all he is thinking about is you, he's letting you know he's not good at the dating game like most of us guys.
No, he just thinks you're much too good for him.
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He means you're such hot girl than why talking with this dick head...
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