I asked out my best guy friend, Joe, and he said no, said it was too soon after his latest break up. I completely understood, and later on he told me he liked me too. When do you think is enough time to ask him out again?

 

Dave: Meet Joe, smart guy. Joe appreciates the value of a good friend who happens to be a girl. He knows that’s a special thing, but a very delicate relationship to maintain. These days Joe is also keenly aware of just how fleeting girlfriends can be. So Joe is putting some serious, serious thought into whether he wants to risk losing his best gal friend if she morphs into his new girlfriend. That Joe, he’s one thoughtful dude.

Bill: Why don’t emotions have expiration dates on them like milk cartons? After a certain date, you’d know this guy was ready to date again. Since your already good friends, you can keep asking him how he feels—maybe even make a joke about it. But don’t put too much pressure on him. You wouldn’t want your new relationship to spoil before it begins.

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