[Edited by Dhampy, 9/17/2009 10:16:31 AM]
College coaches do it during training camp and NFL coaches did it before free agency (think: Knute Rockney and Vince Lombardi for real-life comparisons).
But it appears as if he's going about it in the completely wrong way and it won't work. He's being awkward and thoughtless about it.
I hate to see what he'll try to build you back up with.
If the person says yes, you will be thrown out of your element. You will need to adopt some change to routine. You'll have to step out of your comfort zone.
It's the same kind of fear of acceptance that one would feel when applying for a job which one would have to relocate for. It'd be awesome if you got the job, but then you'll have to pick up and move.