The first thing to do when you find yourself attracted to a shy man is to question your feelings for him. In other words, ask yourself "Am I attracted in spite of or because of his shyness?"
- If you like him because of his shyness, ask yourself further: why do you find shyness attractive in a man? Is that feeling authentic? Do you like his shyness only because you feel like you can't get a confident man? Do you not mind being more socially powerful than him? Women who are attracted to shy men are sometimes manifesting their need to feel dominance over a man (e.g. because they had an absent or abusive father). Other times they run to shy men after being rejected by a confident one (an "Asshole").
- If you like him in spite of his shyness, ask yourself further: could you respect a shy man? Would you admire him? In 10 years, will you still find it attractive? This is important because you need to know if his shyness will ultimately be an impediment to a serious relationship. If you know - deep down - that you could never be with a man who doesn't have the balls to pursue you, then you shouldn't waste your time with him (or waste his time with you).
If you answer these questions sincerely and still want to date him, you then face the problem of making it happen - or rather, making him make it happen.
I used to be shy. My little brother is shy (with girls). A very close friend of mine is extremely shy, and I know plenty of other guys that are shy. For me it is a familiar mindset. Shy guys, almost by definition, do not have the balls to initiate and pursue women. They fall outside of the predator-prey model for sexual interactions that is assumed in the "don't initiate contact" rule. So it is acceptable for you to initiate with a shy guy. But there are a couple caveats...
The problem with male shyness is that it wears off in specific situations. A shy man may never become courageous enough to approach women in general, but he can eventually grow comfortable with a girlfriend or wife. As the fear of the unknown dissipates with increased familiarity, a shy man's confidence in his interactions with you will rise. His masculine instincts will kick in, and in some cases you can end up with a man that acts towards you the same way that a confident man would have acted from the outset.
So, if you do choose to initiate, do so only during the early stages of dating, that is, until he builds his confidence and comfort around 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. Though he knows his own limitations (as prescribed by his shyness), he also knows what a typical man is "supposed to do." So he recognizes, too, when you are doing it for him. This will offend him if you flaunt it, or if it is evident due simply to the social magnitude of the task you've assumed (for example, if you take his hand and lead him through a crowd). That offense will reflect negatively on you and the relationship. So be careful about how much (and which) initiative you take. 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.
So how do you initiate? 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. 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. 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):
- If you would touch him lightly on the arm for 1.5 seconds, hold the contact for 4 or 5 seconds.
- If you would hold eye contact with a confident man for 2 seconds to show him that you are interested, hold a shy man's gaze for 3 or 4 seconds, or do it repeated times.
- If you would normally drop a single verbal hint that you'd like to hang out sometime, do it three times before expecting anything from a shy man.
- If you would normally expect a kiss on the second date from a confident man, wait until at least fifth or sixth to be kissed by a shy man - and in fact, you should probably just make this move yourself.
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.
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. Comments like "Oh, I thought you were going drive/get the tickets/plan the trip/[insert other traditionally masculine roles here]" can help in priming his confidence if it seems to be lagging and it bothers you.
Dating a shy man takes a lot of initial investment for an uncertain outcome. 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. Shy men have taste and standards too. 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. 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. (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. Due to the lack of female attention he has attracted or received, he is like an emotional spring that you will release. If you are looking for an abundance of devotion, he has it to give.
So, in conclusion, if you are interested in a shy man, start by questioning that feeling. If his shyness is not a deal-breaker for you, you can initiate, but you need to be careful about striking a balance between sending strong enough signals and not offending his masculine pride. It is a difficult tightrope to walk, but the consolation is that these men rarely receive attention from women, and have a lot of love and devotion to give you.
1. The More Confident He Is, The Less He Likes You
2. Don't Initiate Contact
3. Learn How to Be Social