Acidity in fruit such as apples will often make sweet wines taste dry. Chocolate works with very few wines. Pudding wines come either as naturally sweet and are the hardest to place, or fortified which, because they are so much stronger, often work better. As with other foods, the more complicated the dish the harder it is to match with wine.
Light Côteaux du Layon, sweet German or Austrian Riesling Auslese or above, Recioto di Soave, Hungarian Tokaji.
Bread and butter pudding
An underrated pudding that goes well with fine wine like Sauternes or other noble rot-affected wines eg Barsac, Monbazillac, sweet Vouvray, Alsace Selection de Grains Nobles. Push the boat out.
Rich fruit cakes
Dark sweet fortified wines like Cream Sherry, Malmsey, Setubal, Oz Liqueur Muscat, Banyuls, Muscat de Beaumes de Venise. Pot of good tea; Scotch or Brandy.
Light cakes and fine biscuits
Fine sweet German Rieslings.
Vouvray, Montlouis moelleux, Côteaux du Layon, Alsace Gewürztraminer Vendange Tardive or Selection de Grains Nobles, Austrian Trockenbeerenauslesen, Reciotto di Soave, Tokaji.
Sweet fortified Muscat (Muscat de Beaumes de Venise), Australian Liqueur Muscat, Setubal, Cream Sherry. Moscato d'Asti, Asti Spumante works well because the light and fruity wine counters the richness of the pudding.
Same as for bread & butter pudding.
Sweet fortified Muscat such as. Beaumes de Venise, but also sweet Jurançon, young Sauternes, young sweet Loire, sweet Scheurebe from Germany, Eiswein.
Monbazillac, fortified Muscat.
Moscato d'Asti , fruit Eaux de Vie, Grappa, Pedro Ximenez Sherry (poured over vanilla ice cream).
Vintage or Tawny Port, Madeira, Banyuls, Vin Santo, Oloroso Sherry, Tokaji.
Asti Spumante or Moscato d'Asti.
Fine Patisserie (without chocolate)
Sweet Champagne, or other sweetish bubbly.
Sparkling Red Loire, Fleurie or another Beaujolais that is not tannic.
Moscato d'Asti, Beaumes de Venise, but maybe something finer like a mature Sauternes from a good vintage.
Sauternes, Vouvray Moelleux or sweet Champagne.
Strawberries and cream
Sweet Champagne, Sparkling Red Loire, Sauternes, Vouvray Moelleux.
Setubal, Australian Liqueur Muscat, Austrian Trockenbeerenauslesen, young red Banyuls, Sparkling Red Loire, Sparkling Shiraz.
Tiramisu & profiteroles
Vin Santo, Moscato d'Asti.
And last but not least, all things chocolate Never, never, never serve with fine pudding wine such as Sauternes, Vouvrays or worst of all delicate Auslesen. Chocolate kills almost everything!
Chocolate does work well with certain fortified wine such as Muscat (Australian, or Beaumes de Venise) it's not bad with Malmsey, or sweet Sherry but is best of all with an old Banyuls –wonderful! Chocolate also works well with spirits and full strength liqueurs (hence liqueur chocolates). Fine milk chocolate works well with a glass of fine Brandy or Grand Marnier. I find plain chocolate is better with whisky or Rum.