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Undateables Ranjana and Ali
Photograph: Ryan Bourque

Meet the Undateables: Ranjana and Ali

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 Ranjana and Ali to tropical Gitano Island on Governors Island—read on to see how it went. 

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

Undateables Ranjana and Ali
Photograph: Ryan Bourque


Ranjana is a 26-year-old writer. 

Ali is a 24-year-old global investigations analyst.

Why they’re single: 

Ranjana is traumatized from past heartbreak so she ”keeps her feelings shallow” and throws herself into her work and friendships.

Ali is “too picky and very busy.”

Ideal date:

Ranjana: A date that is mentally stimulating, including going to a museum, a movie or an arcade. “Something that makes my mind work, followed by a nice dinner.”

Ali: Something outdoors, like going to a park or on the water like kayaking, canoeing or a boat tour.


First impression:

Ranjana: “He was handsome and well put together. It’s funny how it got started—I saw him on the ferry and I figured it was him. He was standing at the bar at first. They seated me and we made eye contact.”

Ali: “I thought she was really cool. She was really nice and had a pretty smile. We started talking right off the bat. She is really career-driven and focused.”

Undateables Ranjana and Ali
Photograph: Ryan Bourque


Ranjana: “We talked about our upbringings, our families and jobs—traditional get-to-know-you stuff, but the conversation kept flowing and I think we really did have a spark. There never was a quiet moment. It was like talking to a friend you’ve known forever. It was really comfortable.”

Ali: “I got more of a friend vibe. I don’t look for physical attraction first, but I was not too attracted to her.”

Awkward moment: 

Ranjana: “I think it was definitely when we made eye contact twice before knowing that we were each other’s setup.”

Ali: “It was during getting our photos taken—the photographer had us walk to take pictures of us, so we had to make fake conversation.”


Ranjana: “After dinner, we took a quick walk on Governors Island and then we took the ferry back to Manhattan. We were talking so much that we didn’t realize the ferry had reached Manhattan and everyone else had already left. We hugged and said ‘goodbye’ and exchanged phone numbers.”

Ali: “On the ferry back, we exchanged numbers and social media. I was running late to my job, so I gave her a hug and went to the train.”

Verdict [on a scale of five hearts]:

Ranjana “Five. Easy! I didn’t expect it to be as easy as it was. I am good at conversation but I was expecting there to be awkward silences and filling in the space with banter, but the conversation just flowed organically.”

Ali: ♥  “I told my friends that I had a great time getting to know her, but I didn’t feel a spark or any real connection.”

The Date Spot:

Our daters went to tropical Gitano Island on Governors Island.

Ranjana: “It was beautiful, the service was great and the drinks and food were great. I really liked it.”

Ali: “I loved it. It was my first time on Governors Island and taking the ferry. The drinks and vibe were both amazing.”

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 Ranjana and Ali
Photograph: Ryan Bourque
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