So few of us are interested in sweet wines. My suggestion is to give it a try. You might like it. These would include sherry, port, sauternes, ice wines, and demi sec sparklings. I do not include “pop” wines, or fruity and sugary faux wines.
Which are sweeter? Winespeed: If a wine has any natural grape sugar left—that is, if some of the sugar was not converted to alcohol during fermentation—then the wine is said to have residual sugar. In order to be considered a sweet wine (not a table wine), a wine has to have quite a lot of unconverted natural grape sugar. According to European Union legislation, for example, a wine labeled “sweet” must have at least 4.5% residual sugar. Most of Europe’s great sweet wines, however, have considerably more than that. Port, Sauternes, and German TBAs are all sweet, but nothing compares to Spain’s opulent Pedro Ximénez sherries (PX), which have over 40% residual sugar. PX wines are nearly black in color and have a texture as thick as maple syrup. A small glass is more than dessert wine, it is dessert.

You already know my port stories from Portugal. And my Sauterne stories from France in 2019. I am not crazy about ice wines, but I know many people who are.
My suggestion, as a way to start, is to try a dry sherry as an aperitif. Try it neat or with some crushed ice. You will be pleasantly surprised. Start with a Taylor or Sheffield before graduating up to the more expensive bottles. Sherry is also great in several casseroles and slow cooked dishes. And I guarantee it works as a great aperitif!
Port is traditionally a dessert wine, though some can be used as an aperitif. The classic pairing is with dark chocolate. Since I am not a chocolate guy, I prefer my port either alone or with a medium soft cheese or dried nuts (I prefer almonds or cashews). You know my escapades across the Portuguese countryside in search of vintage ports. Hint: if you can find any splits, I strongly suggest buying them immediately. Unless you have a house full of guests, it is impossible to finish a bottle of port in one or two nights.

Best of all, you can start with a California port from my home area, Ficklin. They make some great wines and ports. Start with one of their tawny ports, relatively inexpensive, before graduating to the vintage ports. Of course, you can try any of the ports from Porto, if you have a decent budget. Believe me when I tell you that we spent a goodly sum of money in Portugal on vintage ports, some of which are still in the wine cellar.
Some port rules? For most of its history, Port was matured in the lodges by law—a system that effectively insured that the big Port shippers monopolized the trade and that small growers were excluded from creating their own brands. That changed in 1986, and today Port can be, and often is, aged, bottled, and shipped directly from the farm estate (called in Portuguese a quinta). Today there are more than 100,000 vineyard properties in Portugal’s Douro Valley, the region from which all Port comes. These are owned by the shippers themselves, as well as the region’s roughly forty thousand growers, each of whom owns, on average, no more than a scant acre of vines.

A little side note here: If you want to really enjoy the port, please get some really nice cordial stemware. It will enhance the experience exponentially.
Moving on to Sauternes, like I said, I was there, and I thought I gave them a decent try, The locals are quite proud of their Sauternes. It almost seems rather cultish. We tried it after a nice dinner one night, along with a semi sweet dessert, an apple tart. Perhaps if I added some crushed ice, perhaps it would soften and be less sweet. It is obviously an acquired taste.
Was I happy getting to Sauterne? It was certainly different. And it is a charming little village.
The German TBA or trockenbeernaulese, otherwise known as a rather medium to full bodied dessert wine. Aside from their high sugar content, they are botrytized (noble rot), picked very late obviously. While I am not a fan, I have tried a few. Sweet wines are an acquired taste. But a good German strudel with a TBA could work on a cold winter’s night.
Some of the sparkling wines,, called demi-sec are on the sweet side. They are usually labeled as such, or perhaps under the label doux, demi-sec, or names like Moscato, spumante, or Franciacorta. I would try them, since you never know what you might discover. Such as the case when my Italian waiter in Chicago offered me a glass of Franciacorta. It was quite good with my charcuterie.
Much like other wines, the pairing is the key. A fairly neutral pairing, like an almond cookie works well with the sweeter wines. Stay away from the sweeter desserts, and chocolate (except for port).
Please give them a try!