Welcome to the boards, Jenn.
For a white, I would suggest a German Riesling Kabinett or Spatlese. Spatleses are bigger, more lush, and often sweeter than Kabinettss. Or else an Alcasian Tokay-Pinot-Gris (I have found TPGs to pair well with cheeses such as Asiago). Most of the TPGs are dry or just slightly off-dry. There are so many good producers of these wines, but you won't go wrong with...
Muller-Catoir (through 2001)
You might also try a Riesling from Austria such as a Prager.
For a dry red, the wine that first came to mind is Zenato Ripassa. Ripassa are Italian wines made from Valpollicela grapes but on the pommace of Amarone. The result is a wine of medium-full body with a rich texture, a long finish, and good length -- but without being overpowering. Zenato is, generally, my favorite producer of Ripassa and this wine regularly recieves praise on the WS boards.
For the chocolate, I would go with a Port. You can get a good LBV Port without breaking the bank. Try the 1997 Taylor Fladgate LBV -- it is about $20.