Peanut-butter-and-jelly sandwich
Whether it's a late night or just a lazy night, PB&Js deserve to be served with (and require) a wine that's refreshing and a bit sweet.

The easy choice: Don't laugh: Wesson wants you to open your mind to White Zinfandel. He calls the pairing with PB&J "White Zin's highest and best use. [It's] easy to malign, but it gives milk a run for its money."
Easy: Buehler Vineyards Napa Valley White Zinfandel 2005 ($10)

The adventure: For a high-end experience, go with a demi-sec Champagne. They're the "driest version of a dessert Champagne, but aren't so sweet as to ever taste cloying," he says. And you won't even need a spoon to clear the top of your palate of lingering peanut butter - the Champagne's scrubbing bubbles will take care of that for you.
Adventure: Veuve Clicquot Ponsardin Demi-Sec Champagne NV ($48)

Canned chicken noodle soup
Liquid on liquid is, forgive the pun, a "slippery slope," says Wesson.

The easy choice: Portuguese Vinho Verdes provide a refreshing break from the salt in canned soup. The lightly bubbly beverage is also just plain fun to drink.
Easy: Famega Vinho Verde 2006 ($6) 

The adventure: For an "esoteric combination," Wesson suggests a Fino Sherry. The fortified wine, which is a swell match for salty foods, will feel heavier than the soup, upending the texture contrast provided by the lighthearted Vinho Verde.
Adventure: Domecq Dry Fino La Ina Sherry NV ($17)

Barbecued ribs with a slightly sweet vinegar-based wet rub
It's all about wildly fruity reds for this sweet, tangy dish.

The easy choice: A Beaujolais Villages will have you sipping pretty with your
napkin-busting meal. But don't go for a fancy Beaujolais Cru - you want a young "grapy and shamelessly gulpable" Beaujolais, Wesson says.
Easy: Domaine Berrod Beaujolais Villages 2005/06 ($12)

The adventure: It's time for the bubbly soda of wines - a dry Lambrusco. Though they're treated with great respect in their home region of Emilia Romagna, Italy, they got a bad rap in the United States during the 1970s when cheap versions were widely distributed. Since then, they "have really come into their own," says Wesson. "They're complex wines with real substance to them."
Adventure: Pederzana Grasparossa Lambrusco 2005 ($18)

Pizza — half pepperoni, half mushroom
You may go halfsies with your significant other on the pie toppings, but both of you can share the wine.

The easy choice: Chianti’s the obvious answer here — but you don’t want an aged Chianti. Go for a young, fairly fruity example. The acidity will cut through the fat of both the pepperoni and the cheese, and its hint of earthiness will echo the boskiness of the mushrooms. So, no Classicos or Riservas. Stay young.
Easy: Cecchi Chianti DOCG 2005 ($11)   

The adventure: Be daring: Leave Italy, and head to Spain for a Rioja sin Crianza, which is fruity and forward and pairs well with pizza.
Adventure: Bodegas Sierra Cantabria Rioja 2004 ($14)