Though you may be able to finish an entire pint of Ben & Jerry's by yourself, we still think desserts taste best when shared with a loved one. Don't worry, big eaters: with these super-size sweets made for two, you'll still get all the calories you crave.
Gelato? That's amore at Quartino
Don't be fooled by the small plates at this River North establishment, because dessert is another story entirely. While the menu includes Italian classics like profiteroles and various uses of limoncello, the Gran Coppa Quartino takes the cake for two-person treats. Roasted hazelnuts, biscotti and berries adorn scoops of vanilla, chocolate, and strawberry gelati in an oversized, frosted martini glass. For the less-traditional romantic, there's also a raspberry, orange, and lemon sorbetti option that incorporates some of that homemade limoncello.
Find a cupcake to love at Dinkel's
Dinkel's is the sort of place where your grandparents might have met. Don't expect a fancy atmosphere here: this is a working bakery in the Bavarian tradition, family-owned and operated since its inception in 1922. Take a number and belly up to case after case of donuts, cakes, cookies and the absurdly delicious cupcake. You'll find only two flavors here: chocolate or vanilla, each with either chocolate or vanilla icing – and sprinkles, of course. You can have a mini all to yourself, but the regular size is just right for two without going overboard.
Get it on with the biggest cookie you've ever seen at Bittersweet
It's enough to make your jaw drop. Alongside Bittersweet's immaculate assortment of pristine French pastries and authentic macarons, one cookie stands out. It's chocolate-chip-filled, half dipped in chocolate, and roughly the size of your face. As with everything at Bittersweet, the miracle workers in the back are doing something right, as this cookie sacrifices not an ounce of taste despite its uncommon size. Enjoy it in the café's romantic atmosphere with a cup of homemade hot chocolate if you need even more sugar.
Do anything for ice cream at Margie's Candies
It might not seem like a winter-friendly activity, but believe it or not, eating ice cream actually makes you warmer. Sort of. Anyway, true ice-cream devotees will gladly ignore Chicago winters to hit up this classic spot. Everything Margie's serves is good (and good-sized), but if you're feeling adventurous, you might want to go all out and get the Royal George, billed simply as the world's largest sundae, and costing a good $50. Perfect if your lover is a big eater, or if you've skipped dinner (and maybe lunch) and headed straight to dessert. If not, you may need to call in reinforcements, or opt for the slightly more realistic World's Largest Terrapin, which clocks in at a mere 15 scoops of ice cream. We warned you: these are not for the faint of heart!
Light your fire at Hala Kahiki
Okay, we admit it – Hala Kahiki is a bar, not a dessert spot, and it's a bit far off the beaten path. That said, there's enough sugar in this place to keep a small elementary school happy. Tiki rooms complete with statues, fountains and pufferfish lamps await you in a tropical paradise where most drinks are made with ice cream or chocolate as well as booze. And while many of them are huge, the Volcano is specifically for two. No drink is more dramatic: out of its center, a ceramic volcano rises, filled with high-proof rum that gives off a steady burn. If you aim to impress your date and can make the trek, Hala Kahiki should take care of the rest.