Everyone has had that awfully awkward first date that you hate to relive, but must keep telling the story over and over to your friends. Fear no more! Here are my favorite stories, along with suggestions to ensure this never happens to you again.

Sub-Rule for all Rules: Always Meet and Dismiss in a Crowd

Most importantly, you never want him/her to meet you, pick you up, or even drop you off at your place.

The Awkward Date: A friend of mine had a guy walk her home, and he was persistent on coming upstairs. Since her answer was a firm “NO”, he then asked for her phone number and texted her the word “ROSES.” When asked what that meant, he then responded, “I just sent you roses. Can I come up now?” True story, Scout’s Honor.

A nice place to avoid this situation is to meet at Benchmark. This Old Town newbie is sports bar meets trendy. Very beautiful people, added with sports fanatics, added with the varying crowd of Old Town. You can then stroll north on Wells Street until you reach North Avenue, kiss goodbye and catch a cab— by yourself.

1510 North Wells Street
Chicago, IL 60610
(312) 649-9640

Meet for Drinks First

Meeting for drinks helps ease the tension because A) liquor relaxes you, B) it is not an awkward situation to wait at the bar for someone, and C) if the first date goes badly, you have a quick escape route rather than having to sit through a whole dinner.

The Awkward Date: Upon being set up with a girl we will name Jane, my friend, whom we will name Bob, met on a fun night out at Purdue University. Well, with college comes lots of drinks, which Bob had a lot of. Near the end of the evening at Harry’s Chocolate Shop, we all watched Bob turn to Jane, get sick, and then try to kiss her. Needless to say, she was able to make her quick getaway. You know we have never let him live that one down, and I’m sparing you the details.

My fabulous suggestion for this topic is Epic. This is a restaurant/lounge, and suddenly, come 10:00 PM, it’s party city. You can stick around for a couple of drinks or call it quits. The end of the evening is up to you.

112 West Hubbard Street
Chicago, IL 60654-4504
(312) 222-4940

Go Somewhere Fun, but Not Too Out-of-the-Box

We’ve all seen it in the movies; the well thought out, romantic first date that goes completely awry.

The Awkward Date: A friend of mine took a girl to the Broadway in Chicago show, “Chicago”, for a first date that he knew would be a hit, or so he thought. They met for drinks at the Walnut Room before hand and, upon handing her the ticket, she stated, “Now, you only asked me to this so no one would think you were weird for going to a musical alone, right?”

A great suggestion to avoid this is, don’t go out with people this shallow in the first place. Or, you can hit up La Madia’s Wine 101, which takes place on the last Wednesday of every month. Here you have the socializing, the great wine and an impressed date. The sommelier does a great job explaining the wines and making sure everyone is having a great time. Bonus, each person gets a $10 gift card to use after the class for dinner.

La Madia
59 West Grand Avenue
Chicago, IL 60654
(312) 329-0400

Meet for a Casual Dinner

This avoids the “he/she ate like a slob” table manners humiliation. It also ensures that the person can’t drink too much, due to the fact that they have to eat and drink at the same time.

The Awkward Date: I met a guy at Keefer’s for dinner, which is a nicer place to enjoy a meal. Being the girl who has taken her fair share of etiquette classes, people with bad table manners tend to repulse me. We both ordered the chicken, which contains bones, and all throughout the meal, my date was picking chicken bones out of his teeth. Well, since I couldn’t stomach my meal any further, he then asked to finish mine and continued to devour my plate. Bad etiquette in a restaurant as formal as Keefer’s is a big no-no.

Way to avoid this situation: Go to Moe’s Cantina in Wrigleyville or River North, where food is already a little difficult to eat. Many of their dishes must be eaten by hand, and it is casual enough where table manners aren’t really a factor. Nachos, tacos and empanadas all have to been eaten awkwardly, but are delicious.

Moe’s Cantina

3518 North Clark Street
Chicago, IL 60613
(773) 248-0002

155 West Kinzie Street
Chicago, IL 60654

Don’t Cook Dinner If You’re Just a Beginner

The Awkward Date: A guy once wanted to make me dinner because he was just starting to get into cooking shows. However, when I got to his place, I spent most of the date watching him scramble because he was cooking too many things at once. I watched one dish after another go in the garbage, and, an hour and a half later, we were able to eat. It turned out pretty tasty, but the wait with no conversation was the killer.

The solution: Take a cooking class together at the Chopping Block. This way you can learn how to cook and impress your date a little better. You can even create your own private class for two called, ‘Just the Two of Us’. Bon Appettit!

The Chopping Block

222 West Merchandise Mart Plaza #107
Chicago, IL 60654-1103
(312) 644-6360

4747 North Lincoln Avenue
Chicago, IL 60625
(773) 472-6700


(credit: feastrestaurant.com)

If You Want Brunch, Don’t Show Up In PJs

Oh yes, this is a true story.

The Awkward Date: A girlfriend of mine had a guy who suggested brunch as a first date because they both turned out to be extremely busy people. While my friend and I both thought a brunch sounded like a cute first date, around 1:00 PM I received the phone call. “He showed up hungover in his sweatpants!” she cried. “Never again will I do brunch on a first date.”

While I still do suggest a brunch as a nice first date, make it somewhere not so casual, like Feast. This Gold Coast and Bucktown favorite gives you the peace of mind knowing that, if the date shows up in pajamas, he will be asked to leave, and you don’t have to sit through the whole brunch smelling his/her liquor-infused breath.


25 E Delaware Place
Chicago, IL 60622
(312) 337-4001

1616 North Damen Avenue
Chicago, IL 60647
(773) 772-7100

Have a plan. If that “plan” ends well, have a suggestion for next time.

The Awkward Date: After a mediocre date, a good friend of mine dropped his date off at home and then went to text his friend to let him know how it went. Without thinking twice about it, he sent the message, “Date was ok. 50/50, nothing exciting.” When he received a response from his date, it was then that he realized his horrid mistake.

While I don’t have a suggestion for “next time” on this one (since there was no “next time”), the second date is always about keeping him/her interested. On that note, stay tuned for my next article on “Chicago’s Best Dating Stories.”

Alycia Nicole

Alycia Nicole

Alycia Nicole
is a concierge in the heart of downtown Chicago and could tell bad dating stories for a living.

Have a horrible date? Let us know about it in the comments section below. PG-13 only, please!