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Undateables Alex and Marissa
Photograph: Ryan Bourque

Undateables: Alex and Marissa

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 Alex and Marissa to Ten Hope for brunch—read on to see how it went. 

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

Undateables Alex and Marissa
Photograph: Ryan Bourque



Alex is a 27-year-old product specialist for a software company and a stand-up comedian.

Marissa is a 29-year-old bookseller and administrative temp at The Met.

Why they’re single: 

Alex moved to NYC without knowing anyone, works from home and also takes a long time to move on from relationships. She’s also been focused on stand-up and admits she’s socially awkward.

Marissa is “terrible at and terrified of dating” and the dating apps drive her crazy because she keeps falling into the “useless lesbian category when it comes to approaching women/enbys at bars.” She’s surrounded by beloved straight friends, so the places they all go out to tend to cater more to their preferences.

Ideal date: 

Alex: Going to a concert.

Marissa: Getting drinks or coffee so there’s an opportunity for talking or doing an activity that neither person has done before.


First impression:

Alex: “She seemed pretty nice, a little reserved but polite. She was wearing a Hawaiian shirt. I was almost hoping to be set up with a jerk or an asshole because there’d be more to talk about.”

Marissa: “She seemed really nice, although it was slow going to get to know each other, but it was a great first impression.”

Undateables Alex and Marissa
Photograph: Ryan Bourque


Alex: “I felt like the conversation was good but there wasn’t any romantic chemistry. We found out we went to the same college in Florida and talked about art history and stand-up. We just have different lifestyles and interests.”

Marissa: “I feel like I need a little more time to figure out if we have chemistry. There were not any pauses in the conversation and we have a lot in common (I’m from Florida and we went to the same University, which is crazy) but maybe not romantically. Platonically, we hit it off pretty well.”

Awkward moment: 

Alex: “It was an awkward situation [in general]. Neither of us had been on a blind date.”

Marissa: “The main awkward moment we recovered pretty well from. We were ordering food and she asked if we wanted to split some things so we decided on a salad and a burger but when we were ordering, she asked, ‘wait, are you not getting anything?’”


Alex: “We exchanged numbers. I don’t think it’s a love match but I could see hanging out and becoming friends.”

Marissa: “We did talk about our connection at the end of the date and we were on the same page — it was more platonic. She’d never been to The Met before (she’s pretty new to the city) and I work there now, so we talked about going to The Met one day and she let me know about her stand-up comedy. We exchanged phone numbers and we walked to the train together and hugged ‘goodbye.’”

Verdict [on a scale of five hearts]:

Alex: “It was pleasant but didn’t set my heart on fire.”

Marissa:  “A good four. It was a great time and we both enjoyed doing something new.”

The Date Spot:

Our daters went to Ten Hope in Brooklyn for brunch. 

Alex: “We had the burrata salad and burger very good and the cocktails were fine! The rest was great.”

Marissa: “It was a beautiful venue.”

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 Alex and Marissa
Photograph: Ryan Bourque