I am not a big wine drinker. I have tried, but I find I really don't enjoy most of them. What I have discovered that I really like is the sweeter, desert wines. I enjoy them not as desert but with my main meal - particularly if it has meat or cheese.

Many people look at me funny when I do that - the "cultured" folk insist they are too sweet to drink with food. When you discuss this with many wine drinkers, they say you have to learn to appreciate good wine. I say that I want to drink what I actually enjoy drinking, not what I have to be conditioned to like.

What are your feelings on sweet wines, and when to drink them?

i enjoy a good Sauternes or Barsac, Ice Wine (Eiswein), Tokaj, with dessert or a cheese plate after dinner. it just doesn't agree with my palate for an entree or appetizer. then again, we should always aspire to drink what we like, not what others tell us to like

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Sweet wines are not only for dessert and cheese....

Nothing wrong with having Port with barbeque, or pot roast. Forget what the experts say...

Knowing nothing about wine as teenagers, Mrs BV and I used to trek over to NY where the drinking age was 18 and buy a bottle of Remy Dupont Sauternes (it's funny I can still remember the label 38 years later) and drink it with a couple rare steaks off the grill. I don't think I'd enjoy the combination today, but I still like a sweet wine by itself: eiswein, port and sherry are still something to savor after a meal or before bed, especially on a winter night.

I like them as a dessert on their own, after the cheese course but before coffee.

Drink what you like, when you like. Odds are that as you continue to drink sweet wines, you'll naturally want to expand your boundaries and try other varietals. But if not, then you've still been drinking what you find to be delicious.

I like ports the most, but also like medium-cost sauternes (which had much more complexity than I was expecting).

Besides heavily sweet wines like port or sauternes, there's another, somewhat obscure option. Since OP is in New England, he may be able to find a Russian grocery nearby, and if that grocery has a liquor license, they are guaranteed to carry some Georgian wines. Many of those wines, while produced with the same process as a conventional dry red wine, have noticeable natural sweetness. Try Kindzmarauli or Khvanchkara (and don't worry: nobody, but native Georgians, can pronounce those names). The only problem is that sometimes you end up with a fake (distribution channels are not reliable enough to prevent this), but the real thing is very likable.

Works very well with foie gras too.

I'm not keen on trying them with meat, but they can be delightful to drink solo.

d'yquem or suduiraut and fois gras is a famous pairing.
vintage port with an apple and stilton pastry is famous pairing.

late harvest reisling is frequently paired with pork or veal.

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One other category for the OP to look into is the sparkling wine.. some of the less dry and fruitier options may appeal to his/her palate.

Drink whatever you enjoy. Life's too short for anything else.

As noted above, there's a whole world out there. I'm fascinated by some of the available Madeiras, and although I think of Marsala as an ingredient in Zabaglione, I've friend's mother, once a young Italian post-War Bride who treats it as the nectar of the Gods. I seem to recall a sweet Lacrima Cristi from near Naples and at least one sweet red from Greece.

Of course, those of us around when wine was almost unknown in the US beyond emptying Chianti bottles for candle holders atop red checked table cloths, recall the drinking explosion among young women introduced to two wines still on shelves (but never to pass my lips)...Mateus Rose and Lambrusco from Riunite. I knew women who, had their sides been pierced by the legionnaire's lance, would have bled Lambrusco.

On the subject of Italian dessert wines...

I suggest seeking out and sampling a nice Passito de Panteleria.... ^

a nice sauternes is the Chateau Guiraud. it's reasonably priced and is a great example of what sauternes can be.

i've had the 83/88/05 of the Guiraud and really like where the 88 is. I found a 750ml of it for $70, so the price was right!

For a nicely priced Sauternes... I suggest Chateau Les Justices... ^

I really enjoy my ports and Ice wine and I used to really enjoy a Muscat Beaumes de Venise. Then I found, and tasted, d'Yquem......