An early-in-the-game date is a date that’s more than just drinks (or drinks and a light bite), but less than a tasting menu extravaganza. (Save that for your anniversary - seems like things are going well so far.) You need a spot where you can have a great time and get to know each other, without looking like you’re trying too hard. A place with great food, that’s easy-ish to get into, and not too expensive. You need one of the places on this list.
Because Spacca Napoli in Ravenswood is off the beaten path, and the space is small, a low-key dinner here feels intimate. You’ll find brick walls, cans of tomatoes on display, a wood-burning oven - and, most importantly, authentic Neapolitan pizzas. It’s also in the kind of tree-lined neighborhood that you can go for a very cute walk in afterward.
Mi Tocaya is a low-key place where you can have a fun, interesting Mexican meal without spending a ton of money. Their menu doesn’t give descriptions of any of the dishes, so you and your date can work together to figure out what you’re going to eat - and there are plenty of creative things to try (like the peanut butter e lengua, which is beef tongue and peanut salsa). If you’re not feeling adventurous, they also have you covered with some excellent tacos and burritos. Whatever you decide to eat, you’ll have a good time here.
Italian is a classic date night option. We’ve all seen The Lady & the Tramp. But a violinist showing up at your table on the second date is awkward (and creepy), and you’re probably not going out with a cartoon cocker spaniel. So it’s a good idea to have a reliable neighborhood joint in your back pocket that’s nice, but not overkill. This is what you get at Bar Roma in Andersonville - simple, great Italian food, and it feels cozy despite the fact that it’s pretty big. The pastas are made in-house - the cacio e pepe is fantastic, but you also can’t go wrong with the day’s special.
Heavy Southern food sounds like a risky proposition for an early-in-the-game date - it’s a more obvious choice for when you’ve reached the “go home and put on stretchy pants” stage of the relationship. But Pearl’s in Edgewater feels like an upscale sports bar that just happens to serve Southern food. You’ll find a mix of Cajun classics, like po’boys and jambalaya, as well as some smaller bar snacks and salads. It’s a casual spot with good energy and solid drinks, and plenty of TVs to stare at if you run out of things to say.
Eating at Pub Royale in Wicker Park can be a challenge. It’s busy, and the hosts aren’t particularly helpful. Luckily, they accept reservations, and you should definitely make one if you don’t want to fight for seats. At the very least, strolling past the people waiting in line to claim your table will make you like you have your sh*t together. Once you’re seated, you can look forward to excellent Indian-inspired food - get the salt cod samosas and lamb dumplings, for sure.
This West Town brewpub is located in a remodeled old theater, which will give you something to talk about for at least three minutes if you’re feeling nervous. The open and airy space feels historical but still modern, with cool steampunk light fixtures and brewing vats visible in the back. The food and beer are both solid - there are interesting bar snacks like fried giardiniere and chili popcorn, and the burger is fantastic.
The Delta is a new bar and restaurant in Wicker Park that’s great for cocktails and small-plate Southern food, and they specialize in tamales. Cocktail-wise, there are a bunch of different “smashes” (made with crushed ice), and also “vases” of drinks that are excellent for sharing. It’s small here, and gets very crowded, so you have the perfect opportunity for an exit line like, “Wanna get out of here? My place is right around the corner.”
5 Rabanitos is a Mexican restaurant in Pilsen putting out some seriously great food, and if your date can’t appreciate it, you may want to reconsider your future together. It’s affordable, BYOB, and always very crowded. So you should do some planning ahead, and get a reservation. Don’t be put off by the cheesy neon signs in the window - they’re actually pretty big on aesthetics here, and they take plating very seriously. There’s a great selection of tacos as well as a huge vegetarian menu, and they make their own tortillas in-house.
So you agreed to meet after work in River North, and it seems like you have only two choices: an expensive Big Night Out at a place like Chicago Cut, or a sceney sh*tshow full of tube dresses and platform heels. Luckily, there’s Centennial, a low-key spot with a great craft beer selection and interesting bar food. Many dishes have an Indian twist, like a pulled chicken sandwich with curry and yogurt, or the curried sausage crepes. The restaurant looks like the hull of an old ship, with lots of wood and metal, and the space doesn’t get crazy no matter how late you decide to stay. So you’ll definitely be able to hear your date when he/she compliments you on your restaurant choice at the end of the night.
If you want old-school Italian that’s just the right amount of fancy for a second or third date, go to Topo Gigio in Old Town. It has some formal touches, like tablecloths and servers in white button-down shirts, and there are twinkly string lights - but this still manages to feel like a neighborhood spot. Everyone seems to be on a Chianti high, and the service is really friendly. The food is fantastic, too. If the night doesn’t go well, it wasn’t meant to happen.
Bringing a person you just started dating to a special neighborhood spot isn’t something you should do lightly - it’s kind of like introducing them to your family. But sometimes you just can’t wait. Mango Pickle, which serves contemporary Indian food in Edgewater, is the definition of a special neighborhood spot: it’s low-key, has delicious food, and it’s family-run, so you really feel like you’ve been invited into someone’s house.
The idea of a casual neighborhood caviar bar is an unusual one, but that’s exactly what Heritage is. The Humboldt Park space is decidedly not stuffy, with an upstairs that’s bar-like, and a downstairs that feels more formal but still approachable. It’s easy to get same-day reservations (which you should, since it gets busy), and the caviar menu has a wide range of options and prices - starting at $10. They also do some excellent Eastern European food, like borscht, pierogis, and pelmeni (Russian dumplings) filled with ground duck. Throw back some Russian vodka and see where the night takes you.
This Logan Square gastropub is next to a movie theater, and has an intimate feel, with lots of dark wood and leather seats. They do upscale takes on British bar food, so there are dishes like fish and chips, bangers and mash, and a Cornish pasty. There’s also living-room-style seating upstairs - use it to hang out after your meal.
We’ve said it about a few other places, and we’ll say it again here: If your date doesn’t like this spot, you should get up and leave. Cafe Marie-Jeanne is a diner-type space in Humboldt Park, serving rustic French food in a low-key way (on dishes or even dented metal platters that don’t match, for example). The most important thing to know is that the food here is incredible - they have a duck frites dish that you should definitely order - and the laid-back service will help keep those early-date jitters under control.