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That offense will reflect negatively on you and the relationship.So be careful about how much (and which) initiative you take.

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.

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.

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 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 they have even the slightest doubt about your intentions they will hold back.

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