The art of pairing dessert and wine doesn’t have to be tricky. Here’s the rule, and seriously, just try to stick by it: a wine should be sweeter than the dessert you are consuming. (The other rule: these go well with “Santa’s cookies”)
So, give these a try and you will likely not be disappointed: Port, Rutherglen Muscat, Sparkling Wine, Liqueurs.
What you want to keep in mind is BALANCE. You want acidity and sugar to be balanced in both the food and wine. If not balanced, the very sweet dessert will make the wine seem more tannic, less sweet and more acidic.
And as you are eating and drinking, consider the aromas (through smell) and the flavors (through taste) of both the dessert and the wines. Decide what you think (it doesn’t matter what anyone else thinks!) they have in common or what they don’t. And if you like it together, then it works. And if you don’t, try again…that’s half the fun!