I throw up in my mouth whenever someone orders a chocolate dessert with candied orange peels and ginger crystals and then says "I'll have another merlot." That's the gustatory equivalent of going to the Metropolitan Opera with your ipod on. There's a reason the wine list has dessert wines on it. If they DO order a dessert wine, most people go right for the Port (because that's all they know), though it may not be the best pairing. For a transcendessimal experience, try some of the following next time you go out:
Vin Santo de Chianti - a roasted-chestnutty angel in a glass with the kind of exciting hot syrup texture you remember from sneaking your grandma's apricot brandy by the fire. Works especially well with desserts featuring cheese, nuts, stone fruits, pineapple.
Moscato d'Asti - can be "ish", as most things produced in great quantity are, but in the right hands, it is a fresh and lively red apple number sparkling away on your tongue with black pepper notes. Very versatile - try with sorbets and panna cottas, vanillas, berries, custards and rich desserts. The acidity and bubbles will help reign in all that cloy.
Sauternes, or any botrycized equivalent thereof - Botrytis is a fungus that, in optimum conditions, shrivels the grape and concentrates all its sugars for some sweet-ass, complex wine. Look also for: Trockenbeerenauslese (Riesling), Lupiac (Sauv Blanc and Semillon, like Sauternes), Selecion de Grand Noble (Alsace). In a year where the crop sees noble rot (the desirable form of Botrytis), Chile's unbeatable Errazuriz (comprised of Sauv Blanc, Sauv Gris, and Viognier) makes a nice alternative to the pricier Bordeaulaises of Sauternes and Lupiac. The slight bit of funk from the rotted grapes is heaven with a foie gras, cheese and nuts, pears. Incidentally, the most expensive wines in the world include Chateau Y'Quiem, a Sauternes producer. Not that price is always a good indication of the ethereal, but in this case, the aristocracy is onto something.
Reccioto del Valpolicella - Not to be confused with Valpolicella, which is a dry wine. In Reccioto, they leave the Valpolicella grapes (usually the doo-wop trio Rondinella, Corvina and Molinara) on the vine to get all sugary, then lay them out on mats to dry. If you are having chocolate and want to try a red other than Port, get on this. It's similar to Port in its raisiny, dried fig thing, but it's not fortified with additional alcohol. Instead, it gets its braces from a natural acidity, which is like warming yourself on a cold winter's night by the fire, not on it.