Dating 10 years younger men
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.
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.
In other words, ask yourself "Am I attracted in spite of or because of his shyness? A very close friend of mine is extremely shy, and I know plenty of other guys that are shy. Shy guys, almost by definition, do not have the balls to initiate and pursue women.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 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.
At most, it is a reliable source of advice for women who want to improve their chances with the opposite sex.