The idea of letting a guy choose you gets twisted in modern dating advice. Women are told to hold back and play hard to get. But showing interest in a guy isn’t the problem. Only a guy with extremely low self-esteem will run from a woman he likes when she really likes him. The problem is when he feels forced into something, or when he senses you have an agenda. A man can tell when you want him to do something out of a need for validation, as opposed to a genuine desire to deepen your connection with him, and it is off-putting.