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Of course, he will question this over and over in his mind, wondering whether you were asking him to hang out just to be friends, or if you wanted something more.

So show him that you want something more - ask repeatedly.

Aside from their innate male tendency to overlook anything that isn't spelled out in black and white, shy men will by default doubt any sign of your affection.

The reason for this is that shy men are more concerned with avoiding the social catastrophe of asking you out and failing than they are of getting you.

This is what prevents them from taking the initiative in the first place.

Unfortunately there is no easy way to discern his true intentions without putting yourself on the line over and over again, and seeing how he responds.

This can be humiliating, frustrating, even infuriating, and it can ultimately still end in failure.

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