Dating a younger coworker
You will probably get frustrated at his lack of response to your initiatives.
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.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.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.That offense will reflect negatively on you and the relationship.
So be careful about how much (and which) initiative you take.
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.
" 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. 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. 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.