I hate having an upper GI. I couldn't even drink all the stuff they wanted me to. Just couldn't get it down so the test took forever because they had to wait for the one glass of chalk to go through me.
Don't give up. There is a doc out there that will find out what is wrong with you. I don't think it is all in your head. Just keep pushing and don't let them blow you off. You know no one cares about your health as much as you do.
I don't think the Chrons Specialist should have been talking about your case with your boss at a social gathering. I think it would be better if he expressed his opinions to you rather than you hearing it from your boss. Just hang in there until Thursday when he has the results of your tests back and see what he has to say. Try to deal with things one day at a time. If you look to the future it will overwhelm you.