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Author: Matt Kirouac:I blame Lady and the Tramp for ruining everyone's perception of how first dates should go down. Spaghetti and meatballs is pretty much the worst idea for a first date. Because when you're squiring someone, you don't need to divulge the sloppy, saucy side of yourself. There's a science to the dating and dining template, one that requires careful analysis of where you should dine and when. What's the ideal restaurant for a first date? What about a seventh date? There's a lot of confusion out there, and a lot of it has to do with those mangy Disney dogs. Here to help navigate the restaurant romance scene is a handy list of best date spots 1-10, plus a little something extra for when you need to sever ties in public. Print this out, post to your refrigerator, and let the dating begin.
First Date Spot
If you're indulging the risk of going out with someone for the first time, keep it casual and non-committal. Cocktails are paramount here. For one thing, alcohol is the ideal wingman in that it makes any awkward scenario easier to tolerate. It's also low-key and easily malleable, so you have the option to extend the evening into a drawn-out, boozy affair, or you can have one drink and nip it in the bud if it's not working out for you. But for the love of god make it a decent bar with decent drinks. It shouldn't be pretentious, loud, or overwrought, either. Drumbar is the perfect middle ground. It's comfortable, chic, and sophisticated without being gaudy, too sceney, or too cumbersome. Not to mention the drinks are delicious, which could serve either as a nice distraction if your date is a disaster or a nice talking point if you actually give a damn.
Second Date Spot
As you're easing in with your potential partner, it's time to start chewing food together. Don't do too anything too splashy, though. Keep it casual, but show that you're into exciting, thoughtful dining and drinking spots. Rootstock would be the perfect answer. The menu is concise, ensuring your meal doesn't turn into a gigantic, confused cluster. Plates are moderately sized, so you won't get too slovenly. The wine- and beer-focused beverage program is thorough and interesting. And the ambience is chill and hip without being too splashy. You're welcome.
Third Date Spot
It's time to introduce a little pomp and circumstance to your burgeoning relationship. Head to Celeste to make that happen. This River North newcomer is the comic book Two-Face of bar/restaurants, minus any nefarious antics. Rather, the ground floor space offers a cool bar scene with several nifty cocktails and some tasty bar bites. Loosen up with your date downstairs before heading upstairs to the more relaxed dining room. The space toes the line between opulent and leisurely, bedecked with a sort of Liberace-esque color palette and bountiful supper club-style dishes (don't miss the ham plate, the octopus, or the Burrata). It won't cripple your bank account, but it will prove you are serious about the trajectory of your relationship at the same time. Plus the cocktail list upstairs is absolutely biblical and insane, which is always beneficial when you're trying to seal the deal.
Sharing is caring, and no better time to divulge how much of a considerate, sharing person you are than with dinner at a tapas restaurant. Now is the time to see how in sync you two are. The couple that shares tapas together stays together, at least for the foreseeable future. Cafe Iberico is a surefire bet, considering how traditional and lively it is. Since you're still in the early stages of your relationship, it's wise to show your special someone that you're fun and of the people. Don't get too ahead of yourself; instead, opt to share patatas bravas and sangria at this River North piñata of a restaurant.
Now is about the time when you're ready to get fancy. You've both made it clear this isn't an unruly one night stand, and you both genuinely enjoy each other's company. So why not spend it together for hours on end over highfalutin food at BOKA? Having recently undergone a substantial facelist both cosmetically and culinarily, the restaurant is hip, exciting, fresh, and stunning. Taste your way through elegant contemporary American plates while throwing back classy cocktails and canoodling. We've reached the canoodling phase of your relationship and no better place than a restaurant that brings the ritz without dessimating your wallet.
The sixth date is a good time to haul out a brunch date. Why? Because at this point you should be spending the night at each other's apartments and wanting to wake up with one another. Since things are getting legit, it's a nice sign to start going to brunch together. There's something so relationship-y about brunch. You don't just go to brunch with a fling. The ideal setting for a brunch date is someplace relaxed, not too loud, and without too much of a pain-in-the-ass wait. Beatrix is a safe bet. Not only is the restaurant lively, fun, and chill, but the food is exciting, novel, and tasty. It's an expansive enough menu to cater to dieters and diet-haters alike, and the atmosphere is such that you'll want to linger and stare into each other's eyes for hours.
It's wise to save sushi for several dates in, because you don't really want to gape your jaw that wide early on. The seventh date is the perfect time to show your bf/gf just how wide you can unhinge that mouth of yours. But if you're going to be eating dinner like a python, it may as well be at a classy place. Like Kai Zan. The offbeat Humboldt Park sushi spot has some of the best sushi in town, in one of the most unexpected locations. Show your date just how privy you are to restaurants by taking him/her here. Sample a bunch of sashimi, nigiri, and maki, or throw caution to the wind and partake in an omakase tasting menu.
Now it is finally safe to partake in the venerable Lady and the Tramp-style supper. We all are smitten with idea of sharing spaghetti with our sweeties, but let's be frank: it's not a good idea until you've secured your relationship. Too early on and your potential mate will be running for the door over your sloppy, saucy self. Once you've established some ground rules and gotten to know one another, it's acceptable to squire one another to a cozy, comforting Italian spot. There's a couple ways you can do this. One is by going old-school at a classic such as La Scarola, or you can class it up a bit with Anteprima. Both are solid Italian locales, each with a very different motif and feel. It just depends how modern you want to feel. Rest assured there will be spaghetti-slurping going on.
At just about the ninth date, you want to lock things down with the wow factor. Now is the time to bring out the big guns and go for a fine dining masterpiece, one that is glamorous, comfortable, and decadent. One that goes by the name of Grace. No better place to get dolled up to the nines and pretend you're a couple of Disney princes/princesses eating intricate degustations with surgical precision. The whole experience is entirely immersive and fancied, ensuring a memorable dinner for the most gaga of lovebirds. You'll pay an arm and a leg for it, but at this point you've committed to one another pretty solidly and are in it for the long haul, so don't be a cheapskate.
Now that you've made it to the tenth date mark, you've reached the point where you should be establishing a place that is "yours," a place that feels special to you both and is consistently reliable for your needs and cravings. Telegraph fits the mold perfectly, unless you're dating a monster who doesn't drink wine. For the wine-happy couple, Telegraph is Nirvana, complete with cozy neighborhood environs, an interesting food menu, and an accessible, dynamic wine list. As long as things continue down the right path, Telegraph has what it takes to be your new go-to dinner and drinks spot.
BONUS: Where to Break Up
Let's face it. In this day and age of OKCupid and Tinder, many people don't make it to the tenth date. So it's handy to have a break up spot in your back pocket, just in case. This can be tricky, but if you have to tear the romantic bandaid off, do it at Margie's Candies. Because nothing says "I'm over you" quite like a gigantic Americana ice cream sundae. Plus it takes the sting out of crushing loneliness.
- Matt Kirouac