What wine to serve with tomato soup and grilled cheese?

Of course you can drink whatever you like, but I would probably go with a light red wine such as Barbera d'Asti. And as has already been said, Champagne goes with everything!

I usually pair my tomato bisque soup and grilled cheese with a spicy Cabernet. It pairs well with the tomatoes as well as the cheese.

There are some great answers above! But for my two cents...
Other than a wine you like of course, I would say try and pair it to the cheese in your sammich. Here is a link for a quick cheat sheet that will help you choose what wines may go well with what types of cheeses. Good luck!

Champagne, of course! :)

I would have a dry white also. Probably a Sauvignon blanc. I am by no stretch of the word a wine snob, so/and/but I would probably have Nobilo or Kim Crawford. Cheap, cheerful, and tasty.
Also, can I come for dinner? I will bring the wine.

I love this question. I usually drink beer with that, but for wine... well, both the foods are pretty sweet, so I would go with a dry wine. Maybe a dry white. Then again, red wine with tomatoes isn't too bad either. For red, I would use Barolo as it has a nice round flavour without being too sweet, to balance cheese and tomatoes.

Are you willing to tell us more about the special occasion? It's not everyday people ask this kind of question.

Looking forward to seeing everyone else's answers.

Pinot Noir