Most Helpful Guy
Yes, you should tell him, but only if he is single.
Most Helpful Girl
I actually wouldn't text that. Despite his shyness, this is something I'd run by him in person. Maybe pull him aside away from everyone, and confess as casually as you can or something. Don't hang around after and stare him down til he answers, just drop the bomb and then be ready with an easy acceptance of whatever his answer is.