Although I can never force anyone to suddenly "get it" and start drinking wine, I'd like to offer the following suggestion for anyone who'd like to blow $100 on the subject and see if maybe, just maybe, there's something there for them. So, without further ado, here's Chris Pratt's "I have $100 to burn and would like to see if I like wine" guide:
1. Get a copy of Jancis Robinson's book, How to Taste : A Guide to Enjoying Wine. This should cost you about $14 including shipping for a used copy. There's no better book for explaining the very basics, and I'll leave any further discussion to her.
2. Buy yourself one good glass. Don't get that cheap crap from Ikea or Crate & Barrel; don't get an expensive teal-shaded glass from The Bon or Gump's. What you need to do is find a fine wine shop in your area that sells Spiegelau Vino Grande brand glasses; just call ahead and ask if they have them. Figure about $8 for one of these puppies including tax. I'd go for the most generic shape possible, probably their Chardonnay or Bordeaux glass. Just the one's fine.
3. Now, you're going to need something to taste. Here are my suggestions:
Lindemans Bin 65 Chardonnay, $8
Bonny Doon Pacific Rim Riesling, $8
Neil Ellis "Sincerely" Sauvignon Blanc
Vin Gris de Cigare, $10
Laurel Glen Terra Rosa
Columbia Crest Grand Estates Merlot, $10
Cline Zinfandel, $10
Freixenet Cordon Negro Brut, $6
Clocktower Port, $10
4. When you're ready to start tasting, make sure you don't have to drive anywhere. Better yet, get a good bunch of folks together to spread the alcohol around a little bit. Tasting's more fun when you can share it with friends, and the more you've gathered together, the more bottles you can open.
5. Enjoy it. If you found yourself liking any of those wines, and if what Jancis has to say is interesting to you, than congratulations. You're a proto-wino. I'll have to warn you, though: it's a slippery slope. Before too much longer you could find yourself doing crazy stuff like driving three hours just to get to that one wine store that sells that weird French stuff you like, or getting to know local wine shop owners on a first name basis [cuz you're that crazy person who special-orders wines they've never heard of by the case].
† Although all of the other wines mentioned here should be fairly easy to find at most US supermarkets, these wines are more difficult to find. I'd try K&L Wines in the Bay Area; elsewhere, you're on your own. Any good screwcapped New Zealand sauvignon blanc should work fine, as would any Chilean cabernet sauvignon - but these are the best inexpensive examples I know of. If there's a Trader Joe's near you, they might have some good stuff hiding there.