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Marty and Nathan at Chateau Carbide
Photograph: Jaclyn Rivas

Meet the Undateables: Marty and Nathan

We sent two complete strangers on a date in the Loop—here’s how it went.

Written by Emma Krupp (Time Out), in association with Maybelline Fit Me

Frustrated by the dating app struggle? We feel you. That’s why Time Out Chicago is relaunching the Undateables, a series in which we send two eligible singles on a date at some of our favorite Chicago restaurants and bars in the hopes of striking up a new spark. Following the night out, the daters report back with their candid thoughts on first impressions, chemistry and (of course) the inevitable awkward moments. This time, we sent Marty and Nathan to Chateau Carbide in the Loop for sushi and drinks—read on to see how it went. 

Interested in being set up on a blind date? Apply today by sending an email to

Marty and Nathan at Chateau Carbide
Photograph: Jaclyn Rivas


Marty is a 28-year-old programmatic strategist in digital marketing.

Nathan is a 26-year-old architect. 

Why they’re single

Marty: He just got out of a long-term relationship and has already given up on the apps.

Nathan: He has high standards and enjoys being by himself. 

Ideal date

Marty: Dinner and drinks or coffee and a walk around the neighborhood.

Nathan: A spontaneous adventure.


First impression

Marty: “He was just a really funny, quick, witty guy right from the jump. I think we hit it off super fast—it was just a really easy conversation.”

Nathan: “Attractive, stylish, well put-together. Pretty immediately I identified that we were on the same wavelength in terms of humor.” 

Marty and Nathan at Chateau Carbide
Photograph: Jaclyn Rivas


Marty: “Yeah, I definitely think there was romantic chemistry. I think the tension-breaking happened really fast, which was nice.” 

Nathan: “I did feel more of the friend vibe. With the photographer there we were joking and being performative, so it was kind of hard to assess whether there was romantic or sexual chemistry because we were being such goofballs. … Maybe in a different setting, once we can be quieter or more introverted with each other, I think that can be sussed out.” 

Awkward moment

Marty: “Well, he was really into the photography, which I appreciated because I was like, ‘Yeah, let’s do it, let’s do something silly.’ And there was one where he, like, went in with a piece of sushi like he was gonna feed it to me and I was like, ‘Stop, we’re not doing that.’ But I thought it was really funny.” 

Nathan: “I kind of felt like people thought we were famous because Jackie [the photographer] was there for a while—we were having the best time with her and just being total crazy people. This other couple was trying to get in on it and do photobombing stuff, but I wasn’t annoyed by it. … We ended up leaving at the same time as them and we got a picture together.” 


Marty: “We walked maybe like a block or two together and then gave each other a hug and that was that. But before, when we were taking the elevator down, he asked me, ‘What are you doing next week?’ And I said I’d be out of town, but that we should absolutely meet up again.”

Nathan: “We followed each other on Instagram about halfway through the date, I think, and we’ve been messaging since then. … Before we parted ways we decided we wanted to see each other again, if for nothing more than to get to know each other better and keep laughing.” 

Verdict [on a scale of five hearts] 

Marty: ♥♥♥♥ “As far as a blind date goes, I don’t think I could have asked for better. Our conversation was super fun, he has a great personality and I think we mesh really well together.”

Nathan: ♥♥♥♥♥ “Oh god, can I do four and a half? If not, five. I had had such a crazy week at work and was so drained. And by the time I left that date, I felt like a new person—so energized, so excited, so happy.” 

Marty and Nathan at Chateau Carbide
Photograph: Jaclyn Rivas


Our daters went to Chateau Carbide.

Marty: “The sushi was absolutely outstanding. And then there were these satsuma mandarin creamsicle popsicles at the end—they were super tiny and cute, but really delicious and citrusy.” 

Nathan: “The food was amazing, the drinks are great, the staff was wonderful and the location is gorgeous. I’d say it’s highly recommended for a splurgy friend date or a nice time out with someone you’re interested in.”  

Maybelline Fit Me foundation was provided to Undateable participants along with concealer, powder and blush. Visit the Fit Me foundation match finder to find the perfect shade for you to wear on your next date.

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