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Super Suave Date Guide To Wicker Park

What makes me an expert on dating? Why should you trust my advice? Well, for one, I don't see anyone else writing this article. It's just me. I mean, you're kind of stuck with me. And therefore, I am stuck with you.

Which is probably similar to the relationship you're stuck in right now with your significant other.

So what is it then? Do you stay stuck, spending every night decaying on the couch with your lovey-dovey watching old episodes of Two And A Half Men as cheesy powder from Cheetos--your favorite snack treat--solidifies around your lips? Or do you get out to Wicker Park for a little bit of romance?

Choose wisely, friends.

The Wormhole


Wormhole Coffee
1462 North Milwaukee Avenue
Chicago, IL 60622
(773) 661-2468‎

Personally, I am more of a hot chocolate or root beer kinda guy, but I can appreciate that other people appreciate coffee. Plus, if you're on a first date, coffee is great. If the person is awful, like they admittedly torture animals or like Star Trek more than Star Wars or something equally horrible, you can ditch out after one cup of Joe.

Wormhole Coffee is a fantastic place, whether you're on a date or not. Wormhole is just about as nerdy as you can get when it comes to pop culture, going a few steps past the typical nerdy posters on the wall with a DeLorean, straight outta Back To The Future, sitting in the window.

Oh yeah, and they have Nintendo.

Quimby's signage print by Chris Ware, on sale now! (credit: Ware)

Chicks Dig Books

Quimby's Bookstore
1854 W. North Ave
Chicago, IL 60622

Myopic Bookstore
1564 North Milwaukee Avenue
Chicago, IL 60622-2008‎

That John Waters meme that has been making the rounds on the internet lately, which admittedly may or may not be real, makes a good point: "If you go home with somebody, and they don't have books, don't [hold their hand]!"

Books are cool and therefore chicks dig them. I don't actually know any chicks, or even if they like to be called chicks, but I'm pretty sure this is a safe assumption. So why is this relevant to Wicker Park?

Wicker Park just so happens to have two of the coolest bookstores in the city. One of those stores is Myopic Books, a gigantic, multi-floored bookstore that has just about anything you can imagine. This is a place to get the classics and the obscure alike.

My favorite book store though is Quimby's, which is also in Wicker. A sleek store, Quimby's caters to all sorts of alternative needs. They carry zines, books, comics, all kinds of wonderful, wonderful things. I enjoy checking out their local zine racks, seeing the products that are handmade by local, dedicated, Chicago writers.

Also, Liz, the manager, is nice to me. I like nice people.


People Need Food To Live

Big Star
1531 N. Damen

1927 W. North Avenue

1537 N. Milwaukee ave.

This is kind of dicey. On one hand, everyone eats, right? On the other hand, people have told me that I tend to stare at them when they eat, that it's weird and creepy, and that they never want to see me again. So, you know, if you can get through a dinner with someone, I suggest doing it. I'll stick to eating alone in abandoned stairwells though.

ANYWAYS, if you do decide to eat, I recommend Big Star. A great bar with great tequila and, more importantly, amazing tacos. It gets packed, but they're worth the wait. I need to emphasize that these are not your average tacos. One example: tacos de panza, with crispy, braised pork belly, tomato guajillo sauce, queso fresco, onion and cilantro.

I would eat one of those tacos so hard… while alone… in a stairwell.

If Big Star is too packed (which is often the case because it's amazing), then try the equally amazing Piece Pizza. Their great pizza is easy to share with that special someone, especially when you each have one of their amazing microbrews. If you're lucky, your date will be on a night they do karaoke.

I bet a great date dessert spot would be iCream. I wouldn't know, I go there alone, but I'm sure it's even more fun when you're with someone! They specialize in ice cream and frozen yogurt, made right in front of you with sweet, liquid nitrogen machine, but I prefer their hot chocolate pudding. I suggest that, especially in these cold months.

Suave pro-tip: order for your date, it's cool, by saying, "some hot pudding for my hot date." AND THEN WINK.

Dudes love getting winked at.

Flat Iron


The Flat Iron
1565 N Milwaukee Avenue

Okay, so maybe things went really well. You and your date are getting along amazingly, darkness comes, but you still want to hang out. This has never happened to me. Things have never worked out for me. Anyways, if they had worked out, or if they do work out in the future, the Flat Iron is where I'd go with a date.

The Flat Iron is a nice, large bar with walls covered in all kinds of painted art you'll find yourself staring at for hours. Find a corner to chit-chat with your date in till 4 am--yeah, they're open late--or beat them at pool. The choice is yours. Then, once the place is closed, make sure to walk your date home and, after popping a mint, kiss them on the cheek.


Mason Johnson, CBS Chicago
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