Well it may be too late to get into perfect physical shape in two weeks but its certainly not too late to start training.

I'd take up weights and running at least and start eating healthily.

It may not make a huge difference by October 20 (although you will feel better) but you'll certainly be two weeks closer to looking good a few weeks down the line, and you're planning on doing this for 5 weeks so at least you could look great by the end.

Plus you'll need to be in good shape to cope with the physical demands and stress of this exercise.

Good luck Dizaster, I'm sure you'll be fine. Just make your first approaches low key, like a friendly word and then walk on, or make a funny comment and then walk on.

I wouldn't worry too much about trying to start face to face conversation for the first week or so, it might be a bit too intimidating and end up being awkward for both parties.

Just build up gradually so that each individual day is in and of itself not too demanding.

You'll be ok, and of course you can share all your embarrassment here at least