Plan On Meeting Someone In Chicago


Chicago is the place in midwest America you can meet a sexy East European tourist - one with a gap in her teeth and wearing a scarf.

So here’s the plan: Go to the Art Institute of Chicago. 111 S Michigan Ave, Chicago, IL 60603

This is the 5th most visited art museum in the country, btw. When in Chicago, I take clients there. It’s an easy place to meet people. Seriously, why bother with becoming an Uber driver to meet chicks. The Art Institute is IT if you like attractive, progressive-minded artistic types who are lonely and desperate.

I’m kidding of course. Sort of. The Art Museum is an easy place to start conversation because you have Floppies all around (see my ebook). As I always say, it’s much easier to start where the person’s mind is and take them somewhere interesting than the other way around.

This place is so good it might be worth buying the yearly pass. That way you’ll attend the gallery parties - which, just to warn you, are full of old people. But they got grandkids, right? Make the investment. Charm a grandma with your interest in her ‘hoots’ she used to have with Cloris Leachman and Mel Brooks. Also, gallery openings are great places to take dates. Girls get to wear a dress and heels, guys get to dust off their 1999 prom tuxedo and put gel in their hair.

Okay, enough playing around. We’re assigning you a mission: Go to the Museum, meet someone new and experience an adventure together. People you meet there are going to be traveling tourists from Bulgaria. And when people travel they like adventure. Think about it. That’s what you like when you travel. Else, what’s the point… And that follows our number 3 rule of being charismatic: Find out what people want and sell it to them.

Let’s talk strategy.

Rightfully so, everyone makes a beeline for the Van Gogh self-portrait. Makes sense. It’s a freaking Van Gogh! It’s impressive enough that it’s in Chicago which is a long way from the Netherlands. But it’s also a bit of infamous art history. Stand under it and soak in the vibes of a bad-ass, tortured artist. But then get away. Truthfully, it’s not much of a conversation piece once you get past the obvious.

"That must have been before he lopped his ear,” you say.

“No,” she says. “It was the other one.”

“What’re you talking about?”

“The ear. He cut the other ear. We forget he used a mirror to paint his self portrait so that’s really his right ear. He cut off his left.”

“That’s cheating in my book.”

“How so?”

“Using a mirror. All my self-portraits are done from memory.”

“Good for you. This is so depressing.”

“Nice weather we’re having though isn’t it?”

“What? There’s drought in California! Children are dying! What sort of heartless bastard are you? Stay away from me! Ahhhh!!!!”

See Van Gogh is not conducive towards positive conversational flow.

So instead check out my favorite, Paris Street, Rainy Day by Gustave Caillebotte.

All you need to do is just stand there and soon you’ll have company of the most discerning type of art babe.

Here’s how it could go:

A girl pauses next to you, putting her hand on her chin and studying the painting.

“What do you think?” you ask.

She turns towards you and smiles. You smile in return. It’s like letting the cat out of the bag in Walmart - full of mischief.

"I like the movement - this plunging perspective.” She gestures with her hand. “It is I think, modern looking. Because of the patenta. No?”

“Well, I don’t know what patena means but that all sounds good to me. You’re obviously knowledgable about art. I’m impressed. I’m happy to run into a professional art person such as you.”

“Yes. I know much about this. You are lucky. What is your idea on this?”

You point at the painting. “I think those people seem unaware their umbrellas are about to crash into each other.”

“Yes. This is true. I did not notice this thing. It is funny, no? You notice this. Ha. Perhaps you are art critic. Ha.”

“Yeah. You notice all the intelligent, deep, creative, meaning. It takes an amateur like me to notice the obvious. By the way, I couldn’t help hearing you have an accent. Are you from Indiana?”

“No. I am from Bulgaria.”

“Really? Great. I like Bulgarian people.”

“How many Bulgarian people do you know?”

“Counting you? One, so far. But hope to meet more. I like you. You gotta a good vibe. Your English is good.”

“And you, where are you from?”

“I’m from the country of East Chicago. We make pizza. You can come. We can get you a visa.”

She laughs. “It sounds like a country I would like to visit.”

“May I ask you a personal question?”

“This kind of question may be scary, no?”

“No? It’s easy. This may seem a little forward of me but I would like to invite you on an adventure.”

“Oh. What kind of adventure will this happen?”

“We walk around the gallery a bit more. You can teach me how to see art the right way and then I’ll take you to my favorite piece of art. It’s called the Bean. Have you been?”

“No. I do not know this.”

“We will take pictures there for you to put on Facebook. It’s great for that. And then, if you still enjoy my company, I’ll take you to Wicker Park where the hipsters roam and there’s a Delorean in a coffee shop, and then we can eat tapas and drink wine and get to know each other better. That is of course, if you are free to do this. I don’t really know your relationship situation.”

“Yes. My boyfriend would maybe disapprove of this idea.”

“Oh, I see. Yes. I understand. Relationships are important. I would want to make sure you did what you need to do to be happy with your relationship.”

“I am joking. I no longer have boyfriend. He went to go fight with Russian army.”

“Oh wow. Um okay. Sounds like an interesting situation. What do you think? Shall we go? Would you like some time to think about it? I can go around the corner and hang with the guard. His name’s Cleavis and he likes romantic comedies.”

“That is okay. I will go. I like this idea of adventure.”

Of course she does.

Hope you’ve enjoyed this Chicago mission. See you out there soon Chicago conversationalists or if you live somewhere else, maybe consider visiting the city when you have the chance.

Incidentally, I’m in Chicago this weekend to teach my Conversation Camp. Would love to see you there. We work on storytelling and making a good impression and being funny and all the stuff that makes you a great conversationalist.

All the best, Wayne Elise

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