Dear Todd,

You, my friend, have the Band-Aid Syndrome.  You’ve been dreaming for so long about the possibilities of what may happen if you broach this subject with him that you’ve grown terrified of the potential (and perhaps nonexistent) pain involved.

Rip off the Band-Aid!

Call up your friend and ask him if he wants to grab lunch sometime.  While you’re eating and chatting, gauge his interest.  Maybe he’s been flirting with you this whole time, but you were too nervous to notice.

And maybe he’s not interested, but would like to be platonic friends.  Whichever the case, you’ll have vanquished this overwhelming weight hanging over you.

— M