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Dating IRL Spring 2016
Photograph: John Khuu

It's a date: River North

Written by
Nick Kotecki

Busy life in a big city often means dating apps get the best of us. But these digital matchmakers can end up taking way more time than actually, you know, chatting up that cute someone at the end of the bar. With us, though, one swipe is all you get. For this issue's dating installment, we played cupid and sent two lucky guys on an all-expenses-paid date crawl through Chicago's River North neighborhood. The pair was treated to drinks at Chicago tiki stalwart Three Dots and a Dash, on to Ramen-san for a quick round of snacks, and over to dinner at RPM Italian. Match or no-match? We let them decide.

Do you want to go on a free date? Email and we'll find you a match!

The daters:

Mark, 33

Marketing communications executive, pop-culture junkie, cookie fanatic; Lakeview

Christopher, 25

Digital analyst, concert and movie lover; Ukrainian Village

Drinks at Three Dots and a Dash

Three Dots and a Dash Dead Reckoning cocktails

Photograph: John Khuu


“Two fruity guys on a date—how could we go wrong with boozy tiki drinks? I don’t think you can go wrong with any cocktail at Three Dots, but the company was super energetic, talkative and fun.”


“I had never been on a true blind date before, but Mark and I established a good rapport quickly. It’s tough not to have a good time when you’re in such a fun atmosphere.”

Appetizers at Ramen-san:

Ramen-san Mantou buns

Photograph: Anjali M. Pinto


“Isn’t throwing back sake bombs what most people do on a first date? We reminisced about our mutual love for Chicago neighborhoods, favorite dining spots and hobbies over a trio of delectable mantou buns.”


“Ramen-san was the best surprise of the night. I was really impressed. The conversation started to flow a bit more naturally at that point and Mark proved to have a great sense of humor.” 

Dinner at RPM Italian:

RPM Italian octopus dish

Photograph: Anjali M. Pinto


“By the end of the night, we’d exhausted most of the typical first-date interview questions (both of us were obviously journalists in another life). He also got me to try octopus, and I’m one of the finickiest eaters you’ll ever meet.”


“I appreciated that Mark took a step outside of his comfort zone and tried the wood-roasted octopus. He was willing to be adventurous, and I learned that being venturesome was one of his many great qualities.”

The verdict:

Mark: ♥♥♥

“Great food and good company equated to a blind-date success story (and first!) in my book. He was real and showed up! As far as another date, only time will tell!”

Christopher: ♥♥♥♥

“I think any first date can be a bit clunky, but Mark and I shared a few laughs and I genuinely enjoyed getting to know him. Numbers were exchanged, so maybe date number two is just around the corner.”

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