Caroline Rules

If you get a favorable response, then take it slow and let things develop naturally. It might be awkward at first, so be sure to ease into things and allow some time for both of you to adjust.

You also need to prepare yourself for a negative reaction: What if he doesn't share those feelings? Will you be able to maintain the friendship, or will it become too painful for you?

My general theory on this is pretty simple: If you care that much about him, then you have to let him know. To me, it's a risk worth taking. Life is too short to be afraid of living it to its fullest potential.