What do you say when a guy says Why did you pick me?

Answer 1

Do this:

Take his hand, and lead him to a place to sit. Some place romantic, like the dropped tailgate of his Ford pickup, or an empty park bench (as opposed to one holding a sleeping homeless guy).

Look deep and lovingly into his eyes, and tell him the following:

"Because you didn't have a brother."

Then ask him if he has a cute, available cousin.

Seriously, you answer him truthfully, but stress to him through it all that you did pick him and that he has no reason to feel insecure.

If he does have a reason to feel insecure, this is not the best time to tell him, but no other time is better, so better to just rip off the scab and hit him between the eyes with it (the sledgehammer not the scab--pardon the mixed metaphor).

Only you know the answer to it. Only he knows why he is feeling insecure, and he is feeling insecure or he would never have asked. Just be honest.