Fact: Dessert should be every meal.
Fact: Beer should be every drink.
Considering how true these two statements are, far too few of us (and when I say 'us', I mean 'you') are ordering a beer with dessert. And that's dumb, because they work fantastically together.
When I mentioned this concept to a friend, she countered with an argument about time: the meal is ending, and a beer can take a while to drink. I understand, and sometimes sympathize — if you're on a terrible date with a nose-picking non-showering narcissist with 3-too-many cats, then you don't want to order a 16-ounce delay to your escape. But I associate dessert with cheery scenarios: good food, nice setting, a date with a healthy amount of cats (less than two). A scenario, you see, that I don't want to leave.
Another friend told me he didn't like drinking at the end of a meal. I told him we're not friends anymore.
So, in our sweet little booze-approved low-cat fantasy, we're going to order dessert, we're not going to regret it five minutes later, and we're going to compliment it with a beer. These are the pairings that'll keep the dream alive:
A bar, a cake, dripped over anything — it's the most popular dessert, in one form or another, and it's got the easiest answer for a beer pairing: Stout. This is a like-on-like flavor match, as the style is known for its chocolate notes.
But a word of caution: do not order a beer you've never tried here. We're not going to discuss different varieties now, but you need to avoid 'dry stouts' — the less sweet, more 'beer-y' tasting ones. Both the chocolate and the beer will taste worse, more like bitter alcohol than desierable flavor. You want a sweet stout, something that's flavorful on it's own to compliment. If you don't know of any on the menu, ask your server.
Now, if you want to add another dimension to your dessert, you can order a Lambic or Fruit Beer to compliment. Think of chocolate with strawberries, raspberries, or bananas; if you've ordered a slice of rich chocolate cake, a fruit beer will act like a topping.
No, I don't mean that nasty holiday mash-up you re-gift to relatives you hate. I mean Apple, Lemon Meringue, or Key Lime Pie — sweet, fruit-heavy, and complimented with a bread crust. You're going to match these with a Belgian. Delerium Tremens or Chimay are a couple names you may recognize — the ones served in those silly little chalices? There's a reason for that: they're 2-3 times stronger than your average brew, though you won't taste the booze. What you will taste is an enhanced crust, and a clean, crisp compliment to the acidity in the fruit.
Carrot Cake and Pumpkin Pie
Heartier desserts that are a different sort of sweet call for a different sort of match. Look for a Nut Brown Ale, Newcastle being the most common, to stay in line with the earthy tastes but still compliment the sugar.
You need an absolutely massive beer to keep up with this flavor profile, otherwise the creme brulee will dominate the brew and will leave an alcohol taste on your tongue. Luckily, every brewer in America now makes a hyper-hoppy IPA that can keep up — though be sure to choose a flavorful one, meaning one you can describe with a word other than just 'bitter'. Take a bite, then take a swing, then listen to your brain say 'What the hell?' in the best possible way.
Picking one beer for 'ice cream' is like picking one haircut for 'humans'. You've got to tailor the choice based on the dessert's flavor. Here's your quick guide (this should look familiar…)
Chocolate, or Coffee: Stout (or a Fruit Beer to add a different dimension)
Strawberry/Fruit, or anything with Cookie Dough: Belgian
Nut-heavy: Brown Ale
This is going to appear similar to ice cream, and yet is the complete opposite. Whereas above we were matching flavors, here we're going to compliment. Think of your beer as the cheesecake's topping: what do you want to add? Stout will give you chocolate, a Brown Ale will add nuts, and a Fruit Beer will add… yea.
If the cheesecake already has flavors — cherries on top, chocolate drizzle, whatever — I'd lean toward a Belgian. With so much already going on, better to play with the qualites of the crust, submit to the cake's and topping's existing flavors, and cleanse your palate for the next bite.