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Undateables: Erica and Michael
Photograph: Ryan Bourque

Meet the Undateables: Erica and Michael

We take two New Yorkers who swear they’re totally undateable and put our matchmaking skills to the test.

Shaye Weaver
Written by
Shaye Weaver

Frustrated by the dating app struggle? We feel you. That’s why Time Out New York is relaunching the Undateables, a series in which we send two eligible singles on a date at some of our favorite NYC spots 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 Erica and Michael to Date Night at The Met—read on to see how it went. 

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

Undateables Erica and Michael
Photograph: Ryan Bourque


Erica is a 22-year-old graduate student and researcher.

Michael is a 24-year-old information security analyst.

Why they’re single: 

Erica: They have trouble getting beyond a couple of dates, plus, during the last couple of years, they've been studying a lot for their master's degree.

Michael: His work schedule can be tough and dating apps are sketchy—he likes to become friends with prospective significant others first.

Ideal date:

Erica: Playing billiards, bowling, going to a museum, playing cards or a board game.

Michael: Grabbing an iced coffee and a baked good to-go and walking around a park, chatting.

Undateables Ryan and Erica
Photograph: Ryan Bourque


First impression:

Erica: “We shook hands and I noticed we were weirdly mismatched—I was wearing a dress and he was in casual clothing. He was friendly and very good at starting conversations. He fits into the sort of people I would end up going out with based on his interests.”

Michael: “The vibe I got from them right away is that they're really intelligent, funny, kind and it felt like they have good person energy.” 


Erica: “I think there was some. We both said we were nervous at first, but we had nice conversational chemistry and it was nice to go on a journey through the Met! We stayed until the museum closed. It was cool how many similar things we had in common. We had a lot to talk about.”

Michael: “The first part was weird because it was photographed, but the second part was great because we got a lot of talking in and found out we have a lot in common. The third section...was not ideal—I don't know what it was, we didn't click as much.”

Awkward moment:

Erica: “At the Met's Date Night, there was live music playing. We got Prosecco and had to listen to the music, but we were still having a conversation and the music was loud so it was hard to hear him over the music.”

“The run up to dinner, trying to find a spot in a fairly unrecognizable neighborhood.”


Erica: “We got dinner afterward because we were hungry, but we wanted to sit after so much walking at The Met. We walked a while until we got to Caffe Buon Gusto for a short dinner. At the end, I asked for his number and we had a short hug.”

Michael: “I was technically going to the same place they were going...but I didn't want to get into an Uber with someone who met me three hours ago, so I ended up taking the train. We exchanged numbers and did a small hug. I waited for their Uber to come.”

Verdict [on a scale of five hearts]:

Erica: ♥ “It went well—it's always awkward to have a first date so the nerves got to me, but toward the end, it was more comfortable to talk to him. In general, it was a pretty solid date. We texted and had a short conversation afterward and I could see myself talking to him more.”

Michael: ♥ I don't know [if I'll see them again]. I will say that I am personally the type to talk to someone a little more before I pursue anything. I really like to be friends before I date them. There's a two-year age gap, which is not bad at all, but there is a little bit of disconnect between our previous experiences. It's not a terrible thing but comes into play because I've been in long-term relationships. It's definitely open and possible, but I'd like more back and forth. I'm a big texter.”

The Date Spot:

Our daters went to The Metropolitan Museum of Art during its new Date Nights program.

Erica: “I have always loved to go to The Met and it generally has pretty intriguing exhibits. It was nice to have a drink on the side and listen to music, which enhanced the experience. Especially for a first date, it was nice to have something else to talk about rather than just work. It was easier to come up with topics and the pressure was definitely off. It's nice to have something different to look're not just staring at the other person.”

Michael: “Beforehand, if you had asked me to do a date at The Met, I would have said ‘no,’ but after doing it, I think it is one of my future top date ideas. The fashion exhibit ['In America: An Anthology of Fashion'] was pretty cool.”

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.

Undateables Ryan and Erica
Photograph: Ryan Bourque
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