Do women have it a lot easier than men, and do hot people in general have it the easiest? Millward created 10 fake OKCupid profiles with similar sounding usernames, with the same written profile, personal stats, level of education, etc. Each account had a different photo of a man or woman of varying attractiveness. However, it’s always good to back up hypotheses with facts, and that’s what Jon Millward did with this experiment, posted on his eponymous blog.As a man, your takeaway is that the competition is fierce, and thus far, you have not been up to it.Stop blaming Match or women or your city for your failures and learn to market yourself more effectively.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 first thing to do when you find yourself attracted to a shy man is to question your feelings for him.
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.
So it is acceptable for you to initiate with a shy guy. 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.