Wine pairing advice usually arrives as a list of rules. Here it is a menu instead. Five courses for one, a glass for each, and a single reason it works.

Menu for One

To start

Oysters on ice, or a tomato and mozzarella salad

In the glass A dry sparkling wine such as Brut Champagne, or a crisp Sauvignon Blanc

Salt and freshness love bubbles and acidity. The wine works like a squeeze of lemon.

The light main

Roast chicken with herbs and its own juices

In the glass A Pinot Noir, or a rounded, lightly oaked Chardonnay

Chicken is mild, so the wine should be too. Pinot's red fruit and soft texture will not bully it.

The big main

Grilled steak with a little char

In the glass A Malbec or a Cabernet Sauvignon

Rich, savory meat softens the grip of tannin (the dry, grippy feeling in strong reds), so the wine tastes smoother.

The cheese

Aged hard cheese, or a creamy blue

In the glass A tawny Port for the hard cheese, a sweet wine such as Sauternes for the blue

Salty and sweet is one of the best partnerships there is. The sweetness tames the salt.

To finish

A dark chocolate tart, or a lemon tart

In the glass Tawny Port for the chocolate, a late harvest Riesling for the lemon

The wine should be at least as sweet as the dessert, or it will taste sour and thin.

Three old rules we broke

"Red with meat, white with fish."
Weight matters more than color. A light red such as Pinot Noir is lovely with salmon, and a rich white can stand up to chicken.
"Never drink red with cheese."
Plenty of cheeses suit red. Sweet wines, though, are often the better partner for the saltiest ones.
"Expensive means better with food."
A fresh, simple bottle often matches a meal better than a heavy, expensive one. Balance beats price.

One rule worth keeping

Match the weight. Light dishes want light wines, rich dishes want richer ones. If you remember nothing else, remember that.

These are classic starting points, not guarantees. Taste is personal. Please drink responsibly.