Ahh the ever elusive food and wine match, What goes with what? What am I going to have with my dinner and What an earth am I going to cook to go with my delicious bottle of wine? There are a few things to take into account when it comes to food and wine matching. I wont go into this in too much depth but these are some of the basics just to keep in mind if your wondering.
From the wine side; how old is it, how big is it, is it sweet, white, red, bubbly
From the food side; How spicy is your food, is your food sweet, how acidic is it, do you have things like capsicum, lots of herbs, bitter vegetables, cabbage
Things to note; Sugar in food makes the acid and tannin stand out like a sore thumb, it can make the wine look really disjointed. Acidic food can make the wine look sweeter than it is and look unbalanced. bitter vegetables, cabbage and capsicum can sometimes make the wine look closed and a little strange, artichokes, just don't go there (that's a hard one and the reaction in your mouth is just outright weird. I do love artichokes though!)
White, rose or white bubbles think dishes that are lighter, include a little fruit or lighter types of meat dishes and the inclusion of nuts like cashews and almonds and breads like brioche and ciabatta can be really great if there is oak involved in the wine. An exception with a couple of red meat dishes that work well with rose and some whites are beef capaccio and beef tatare, these dishes are partially or wholly raw so are a lot 'lighter' than a steak or ragout
Light to medium bodied red, medium bodied dishes such as boef Bourgongne, charchuterie, paella, some duck dishes can fantastic, roasted mushroom and celeriac pasta
Heavier reds, Steak, roasted red meats, roasted beetroot and mushrooms etc things that are more robust and can hold up to the larger wines
Sparkling red, Always has sweetness about it and it goes amazingly with spicy food especially Sechzwan, also pretty well with bacon and eggs or fresh berries on waffles for a cheeky start to the day
Older wine, whether it is white or red, it has to be a dish that is soft, not in texture but in strength. A flavorsome aged scotch steak over coals would be delicious but it will totally kill an older wine and make it appear washed out. Oh and in a side note, let your older wine open up in your glass please. If it is really fragile (as really old wines often are), pouring it into a decanter will be brutal and can destroy it. Sometimes there are only moments left once opened and if your about to indulge in a piece of history, you don't want to miss it. Be gentle, if it takes time to open up, enjoy the journey and watch it unfurl.
What order to have your wine, always softer to stronger, older to youngest, white to red. Mix them up and your softer older wines will look washed out and sometimes insipid. If you think of this in a food context, imagine this - eat an intense dark chocolate pudding then follow immediately by a subltle vanilla and lavender mousse with crunchy meringue, all the second dish would taste like is whipped cream with crunchy bits, your pallete completely overwhelmed by the intensely flavored dessert beforehand.
When I am being really particular about what I am going to match my wine with, I follow the above and I sometimes include ingredients that have similar flavours and smells that I can see in the wines ie champagne - can have citrus, yeast, toast like notes, goes fab with toasted brioche with pine mushroom pate . Most wine aromas have similar aromas and/or flavours in food ingredients.
If you are not quite sure and you have a really good bottle of wine, just have it without food, in between courses or before you eat. It's a shame to open a great bottle of wine only to have it look not what you expected because of what you are eating at the time. Also bring out your better wines as the 2nd or 3rd bottle, not at the end.
That all said and done, wine is meant to be enjoyed and sometimes it really doesn't matter. Enjoy the moment and have fun!