Whether it's your co-worker, your best friend or someone you've never met, we've got the just the thing to turn your nerve-wracking first date into a perfect night in Chicago. So take our advice, stop freaking out and find something nice to wear.
Going in blind
This may be the most dreaded date of them all, even if you've previously chatted and shared photos. The unpredictability of a blind date is enough to make the smoothest dater sweat in his swank duds. But that's because he's probably picked the wrong location to meet up. Rather than a nice restaurant or the old standby coffee shop, we recommend a place that's chock-full of distraction, like Navy Pier. There's so much going on here that you won't even have a moment of silence to feel tense. And you can leave it up to your date to choose the first activity; a ride on the notorious ferris wheel, a drink at one of the venue's pubs or a hit blockbuster in the IMAX.
Too touristy? Try an oddball museum.
The almost one-night stand
Hey, we're not pointing fingers. Those of us who haven't given out our (real) number to someone we met in a bar have at least entertained the idea. But let's get real for a minute. At least one of the parties involved here was looking for little more than a late-night hookup, so you'd do well to keep it casual if you happen to go for round two. You don't want to spend too much money, but you should at least meet somewhere decent before hitting the sheets again. We recommend the Deluxe Diner in Edgewater. Nice enough to say "hey you’re not so bad," and laid-back enough to let your date know that you're still on the fence about this one.
Want to get to bed faster? Find a diner in your 'hood.
Is it really a date?
Your favorite study buddy finally asked you to meet up without the rest of the group. At first you're thrilled, since you've been waiting for this moment all semester. Then it hits you: what if dreamboy just wants to squeeze in an extra study session before finals? Chances are he wants to squeeze in a little more than that, but you don't want to be presumptuous. This is where local coffee houses like Dollop Coffee Co. always come in handy. Neither of you will end up splurging on expensive drinks or dinner, and the unassuming atmosphere is good for studying both the books and each other.
For a truly local latte, search for a coffeehouse near you.
You're already good friends
And now you'll never be able to get that back. But in the meantime, you can relish in the comfort of already knowing each other's dirty little secrets and pet peeves. Since you've probably already done dinner, drinks and all the typical datey stuff together, we suggest mixing it up with a cooking class at the Wooden Spoon. You can test your hand at steakhouse classics or try one of the romance-inspired classes like the Spring Kiss, $65 per person. And if all goes well, you can both put your newfound skills to good use on the next date.
Try these other cooking schools, or head to a restaurant cooking class.
You're both into music
Hopefully you've at least figured out that much at this point. If not, you should probably take a long stroll along the lakeshore together beforehand and ask the typical "getting to know you" questions. But even if your new date doesn't have a defined musical taste, she'll still appreciate the classic jazz and chic decor at the historic Green Mill. Cozy up in one of the club's circular booths and order a classic tipple while you rack your brain for clever things to say (if you can't think of anything, you can just blame it on the fact that you're supposed to keep quiet during the set).
Not into all that jazz? Find a club that fits your style or just pick a show.
You've asked out your coworker
You’re already breaking the rules (never date anyone you work with), so you may as well take it a step further. First dates should never involve bank-draining dinners or truly intimate settings, but you're probably both due for a refreshing escape from the office. And Mr. Trump is just the man to take care of that with his swank restaurant, Sixteen, located on the sixteenth floor of the Trump International Hotel & Tower. You and your date can choose from gourmet dishes like wild Tasmanian salmon and Colorado lamb with trumpet mushrooms. And if you get too tipsy on the restaurant's extensive selection of wine, you can shack up in one of the hotel's luxurious suites.
Can't afford to be that sinful? There are plenty of other hotel restaurants that fit the bill - and probably won't be hosting your co-workers.
You're totally broke
You spent your last dime on the latest iPhone app and now you haven't a clue how to impress on your date, which is just days away. This is where local landmarks like Millennium Park come in handy. Now before you roll your eyes, thinking, Oh God, everyone has been to Millennium Park, take a minute to think about the endless opportunities for conversation here. There will be plenty of unassuming tourists for you both to secretly poke fun at, and a nice walking trail to work up an appetite for later. There are also a ridiculous amount of pubs, restaurants, museums and shops nearby (you know, if your date is willing to fork over some dough), including the Art Institute, which offers free admission on Tuesdays.
Want to get a little more wild? Check out the Lincoln Park Zoo.
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