Book called rules dating
It can be Played for Laughs if a character tries to appear knowledgeable by quoting a rule, only to be corrected by someone else that he picked a completely wrong section of said document. May be quoted from and result in a Sparse List of Rules.
Only remember that the rules and ideas described in the Real Life section of this trope are meant for the battlefield and do not always help a person in social situations and may make you seem like a Jerk Ass or Magnificent Bastard, when compromise and politeness will get you much farther.
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.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. 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.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.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.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.If nothing else, this blog is an outlet for voicing my astonishment at the typical female's ignorance of the male mindset.At most, it is a reliable source of advice for women who want to improve their chances with the opposite sex.