How many times should you ask a girl out for a date before you give up? A friend of ours told us that he would ask a girl three times before he would give up. Why he arbitrarily picked three, we don't know. Probably because in baseball you get three strikes before you are out.

Our rule of thumb is once. If she legitimately has other plans and wants to do something with you, she will communicate this. "Oh, I'd love to, but I just can't. I can make it some other time..." If she is uninterested, she will make herself available.