Sex and the Windy City
- Samantha Miller
- Jul 10, 2018
- 6 min read
Let me start with a confession that might ~stir~ the pot. I’ve never been on a bad first date.
And I’ve been on a lot of first dates.
I feel quite lucky to be able to share this deeply rooted and oh so secretive confession - I know, but I had to share. I’ve heard absolute horror stories where the guys a creep and shows up having done more internet recon on you than you have on him, which was a lot. Like a lot.
Or he shows up twenty minutes late and is hammered. Absolutely plastered. I’m not saying doing a little pre-date pregaming isn’t sometimes necessary, (there is no judgement here, I’m guilty too) but his pregame brought the slurred words and whisky breath to your five star dinner? Buh bye.
IF you’re going to get drunk before a date at least invite me. C’mon.
So, I’ve compiled a list of the hands down best ideas to bring to the (dinner) table, and bars to hop to. Chicago is a city full of endless rom-com-style-date opportunities that will leave you wondering if you’re on an episode of Sex and the City or if this is your real live, actual life.
I have to give an honorable shout out to Des Moines, Iowa for a couple mentions in here too. If you want to drive five hours west to go try them, sure go ahead, I guess. BUT - they can always be applied to our beautiful home right on Lake Michigan here.
It’s Espicy Dinner - The Entrees
I would’ve titled that ‘espicy meatball’ but I don’t eat meat and don’t want to be ~ fake ~. However, I know the in’s and out’s of this city. The where to see and where to be seen, and most of those are too expensive for my baby little wallet so I’ll keep it simple. Make your reservation right now because they’ll fill up quick.
True Food Kitchen - River North
This ‘eco-chic’ LA style chain on Eerie in River North is an absolute gem. The open concept restaurant with an abundance of outdoor seating is the essence of summer dining. My date for this evening had known about my ~special diet needs~ and surprised me with reservations here and a table on the patio. True Food Kitchen boasts organic all made from scratch, well, true food, so I was immediately interested. The foodie inside me awoke - anything could be made vegan?? Are you kidding? This guy knew what he was doing.
The minute we walked in the ridiculously high ceilings and flush greenery everywhere complemented the hospitality of the restaurant. Our waitress was one of the nicest people I’ve ever met - I swear. An act or not, Michelle was amazing and if I had more money on my person I would’ve given all of it to her. 100% tip for you, Michelle.
I ended up getting the cheapest glass of white wine (he didn’t need to know my go to drink was a vodka water (just yet)) and we decided to split two dishes. Again, my kind of man. The vegan pesto pizza and a quinoa teriyaki bowl. Anytime I hear 'vegan pizza' though, I get a little, well, nervy. Before my vegan days - I actually used to *gasp* eat cheese. I know what it tastes like. It’s fucking good. And you’re telling me you can replicate that with a stretchy-doesn’t-really-ever-melt, soy by-product? HA. Alright, sure.
But, oh boy, when that bad boy came around. I had an epiphany. I transcended all of time. Went back to 1 BC saw the beginning of time, touched the dinosaurs, saw them all blow up, did my own hunting and gathering, made some beads, lit a fire and came back all within the blink of an eye. Picture when Raven Symone had a vision on That’s So Raven. That’s how it went down. I’ll never experience it ever again.
If you can’t tell - this place was the best. I recommend it for a first date. For a rehearsal dinner. For a graduation party. Your divorce party. Lunch alone. Dinner alone. Pregame for girls night out. Third date. Seventh date. Take your frickin' grandma here and show her a great meal. It won’t disappoint unless your date is bad. In that case, leave him, find another table, sit back down and I’m sure it will make up for it.
Cindy’s and the Game Room at Chicago Athletic Association - The Loop
If you’re planning the date, take him here. He’ll be so impressed he won’t even see it coming. This is one of the most exclusive feeling places, in my humble-intern-salary opinion, in the city and you don’t even need to be a member to experience it. If he’s not from town and doesn’t know that? Jackpot.
When you walk in, the first floor resembles a mix between a castle, and a prohibition time speak-easy. My date and I were greeted by the hosts at the front desk, and escorted to the winding stairs that made me feel like an absolute princess. The dark hardwood of the library on the second floor and the mysterious dark leather furniture with the floor to ceiling bookcases make an easy conversation starter if this is your first date (which again for me, it was).
If neither of you are impressed yet, the Game Room on the second floor is the cocktail bar complete with any classic bar game you can find. Tables of shuffleboard, pool, darts and some fancy other things I probably have never seen. Popping in here as a barely fresh 21 year-old did make me feel a little out of place with the executives in the room - but I put my priorities in which mojito I’d rather get than dwell.
The grandest part of the Chicago Athletic Association, if you haven’t wooed him yet, would be Cindy’s on the rooftop. One of the highest rated bars in Chicago, and the highest rated rooftop bar is sure to literally blow his socks off.
Really. Bring him a spare.
With incredible views of the skyline, Grant Park and Lake Michigan and drinks that may as well be overpriced but what the hell it’s worth it, Cindy’s is sure to seal the deal. But, if you’re from the wild west (Iowa), and don’t want to trek all the way out here, I’ve got something for you.
Honorable Mention - Des Moines, IA - The Next Portland
Maybe Des Moines won’t be the next Portland, OR, but I think its just as granola-y, with a handful of craft breweries and trendy cafes that make it feel like Portland’s little brother. Here are my honorable mentions for your next date in Des Moines, the most romantic city on Earth (awwwww).
Up-Down - East Village
I honestly wish Chicago had something like this. We probably do, but not yet to my knowledge. Up-Down is a grungy little arcade bar set in the middle of East Village, conveniently next to, surprise surprise, more bars. A dark and smokey arcade bar with cheap drinks and even cheaper games. The ultimate ice breaker. Take your date here to kick his ass at skee-ball or show him that giant Jenga is your thing.
St. Kilda’s - MLK
St. Kilda’s is that trendy cafe you see on your instagram explore page with the avocado toast and the art (lattes) but you never really know where they are. I’ll tell you. St. Kilda’s. Gorgeous, contemporary modern cafe by day - romantic, dimly lit, jazz filled restaurant with expansive wine collection by night. Set in the looks of an old industrial building, the exposed brick and lofty ceilings give it a very Brooklyn feel, from the safety of your own Des Moines neighborhood. My date and I were here gabbing past close and they just closed up around us and gave us our space, and an extra glass of wine. Good guys. Pair a white with the farro and quinoa salad and give it a go.
As you can see, it doesn’t really matter whether you’re in the number one restaurant city in America or in the epi-center of state dedicated to corn and agriculture. As long as you have some good company, plenty of liquor and great eats - you’ll be just fine.
xoxo,
s
Samantha Miller (@samantharachelmiller) is a freelance writer from Chicago. She prides herself on her occasional wit, her keen eye for design and her undying love for iced almond milk lattes.
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