Matching foods and wines can be daunting to some, but it is the most fun part of the wine drinking/cooking process! The following are some tips to help you with your pairings.
1. Balance the heaviness or lightness of the wine with that of the food. A mixed green salad? By nature, light. Would you pair it with a heavy Cabernet Sauvignon? Probably not. What about a heavy stew: a light and fruity red wine… or a robust red? You figure. 
2. Look for flavor links between the wine and the food. Is there a hint of sweetness in the dish? Maybe a wine with a hint of sweetness would be nice too: prime example, a blue cheese-stuffed roasted apricot would pair well with a white that has some sweetness to it as well. Is a Chardonnay really buttery? Perhaps its perfect match is a seafood with a buttery sauce. Finding these similarities and then pairing along these lines is a nice guideline.
The Jocelyn Lonen Cabernet Sauvignon was a perfect choice for Jamie Oliver's proscuitto-wrapped steak: the fruit in the wine balanced the saltiness of the proscuitto, while the tannins and full body of the wine held up to the meatiness of the steak.
3.. Pay close attention to a wine’s structure and texture.
Does it have low or high acidity? It is sweet, or dry? Is it very tannic, or does it have soft tannins? All of these things factor into pairing a wine with food.
4. Most dishes are complex; don’t just pair with one element.
In most cases, you don’t just have chicken; you have chicken with a sauce or herbs, matched with a side veg, etc. When pairing a wine with a dish, consider all its elements–the sauce, the seasonings, the cooking methods, and the main ingredient.
Other tips:
- Get to know the classic food and wine pairings: they will help you understand how food and wine works together to enhance one another! Examples are Sauternes and foie gras, Red Bordeaux and lamb roast, Champagne and caviar.
- Dry white wines tend to be poorly matched with sweets. Sweets need a wine with a bit of sweetness as well: you’d want a Riesling or a Gewurztraminer with an apple tart, not an acidic Sauvignon Blanc.
- Champagne and other sparkling wines are great matches with many dishes because they are high in acidity, low in alcohol, and refreshing on the palate.
- Cheese always helps with pairings! A dish like a vinegar-based salad dressing paired with a tart white wine is not a good combination; add a cheese like chèvre and the pairing works!
- Cabernet Franc is known for its herbal qualities and pairs incredibly well with herbed dishes (and often overlooked for its “big brother”, Cabernet Sauvignon.
-Zinfandel and barbecue sauce are a great combination.
- A big, oak-laden wine will overwhelm many dishes: try pairing it with roasting, grilling, or browning dishes to pair with the wine’s strong flavors.
- Raw garlic, artichokes, and asparagus are all very difficult to pair wines with. Try a VERY light Italian varietal, like Frascati.
- Salty dishes bring out the heat in high alcohol wines.
- Slow-cooked, braised lamb or short ribs are a perfect pairing for an older, mature red wine, not a young red with more prominent tannins.