First, you must know your main red wines. They are Beaujolais, Pinot Noir, Merlot, Cabernet, Zinfandel and Port. Beaujolais is the lightest and fruitiest, making it the easiest to drink; whereas, Port has the strongest and most distinct taste, and it is the strongest alcohol wise as well.
If you are having a wine and cheese night with friends, all of the above wines complement cheese well, so you never have to worry about looking like an amateur during this occasion. If you are doing appetizers, Beaujolais is the best fit. That is simply because it is light and will not overpower your appetizers. It is actually a fun wine, just as appetizers are fun to eat.
For pasta with red sauce, all of the wines will do, with the exception of Port. Red sauce is pretty universal, making it an easy choice for pairing. Simply pick your favorite red.
If you are having poultry (chicken or turkey), your best bet is Beaujolais. The Beaujolais will not give your poultry an off taste, as some of the others might do.
For beef, Beaujolais and Port are the only two that do not complement it well. Beaujolais is too weak, while Port is too strong. You need the perfect balance of bitter yet tasty for beef.
Port is the top choice to pair with chocolate. There is something about the strong, fruity taste that makes chocolate that much more delectable.