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Unfortunately there is no quantifiable or simple rule here, as his threshold for embarrassment will vary in proportion to his shyness and his pride, which are different in every man. Well, for starters, in the early stages, you will need to give him blatant signs of your interest.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.
This can be humiliating, frustrating, even infuriating, and it can ultimately still end in failure.
If they have even the slightest doubt about your intentions they will hold back.
So whatever you would normally do to indicate your interest to a confident man, double or triple it for a shy man (in proportion to his shyness): While I don't suggest that you overtly ask out a shy guy on an "official" date (this would too flagrantly undermine what he knows to be his role as described above), I do suggest that you suggest and then ask him to hang out under casual pretenses.
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.
You will probably get frustrated at his lack of response to your initiatives.
The biggest problem is that it won't be clear to you whether or not his unresponsiveness is a product of his shyness or his lack of interest in you - because it could be either one. His persistent willingness to hang out with you might be stem from a real interest, but it also might be a manifestation of his unfulfilled desire for female attention; he could just enjoy dabbling in the idea of a relationship but at the same time not like you enough to want anything serious with you.Once this happens, you will need to gradually assume a less assertive (more traditionally female) role, because he will then be more liable to get bored with you, wonder if he could do better, consider his other options (the perception of which his newly-found confidence will likely inflate), fool around, etc.The second caveat is that even a shy man has pride.In general, you will need to carry the relationship up until the point that it is "official." When it has been established (or is otherwise clear) that the two of you are together, then you should start reducing your initiative and letting him take the reins.As I said, he will probably start to do this on his own anyway, so rather than forcing it, just be cognizant of the transition.(If nothing else, this will give you good insight into what it is like to be a man.) While all of this sounds like it might be too difficult to deal with - and many women will come to that conclusion - it is worth pointing out that if you can navigate through the difficult aspects of attracting and dating a shy man, he is likely to be completely faithful to you.