Credit: Screenshot, Time Out New York

Dating these days can be hard to deal with, and sometimes harsh truths are exposed when two people are forced to be in an awkward situation together. It’s easy to become discouraged and consider yourself  “undateable.”


In comes Time Out New York. Their "Undateables" section is dedicated to setting up dates with two people who consider themselves “undateable.” The goal is to try and prove that the participants are, in fact, dateable and capable of sharing great experiences together. 


Time Out New York’s recent dating column featured two New Yorkers, Alyssa and Billy. Like any other dating write-ups, the dates can go really well, or they can be awkward disasters.


In the case of these two 24-year-olds, things didn’t work out as planned.


Billy’s first impression of Alyssa let us know what direction their date was heading.

"She was about five minutes late, which annoyed the s–t out of me. As soon as she walked into the room, I knew she wasn't the girl for me. She didn't have the goods," Billy, a 24-year-old actor living on the Upper East Side of Manhattan, said of his first impression.

Alyssa, a 24-year-old video production manager, appeared to be optimistic and honest about her being late for a first date.

"I didn't want to be that girl who's late, and I was trying really hard, but I was about three minutes late. He stood up, and we hugged. He was really nice and charming," Alyssa said of her first impression of Billy.

According to the Q&A-style article, Billy wasn’t really into the chemistry during the date and didn’t quite say if he was attracted to Alyssa.

This particular dating story became awkward, and Twitter had something to say about it.

“Whether I was attracted to her or not, I still had to sit there for two hours and be a gentleman. We had a nice conversation. She complimented me many times,” Billy said.

Alyssa, on the other hand, tried to stay optimistic, despite the awkward date.

“He’s an actor, and that’s totally uncharted territory for me. I like a really stable job in a significant other. But the conversation was very friendly. He did a lot of the talking,” Alyssa said.

When the two were asked to describe their most awkward moment during the date, they were again not on the same page.  

Alyssa: “A couple of times he told me not to be nervous. I wasn’t nervous, but that made me second-guess myself and get in my head. And then the conversation stalled.”

Billy: “She ordered her filet mignon well done. The waiter just looked at me, and I looked at the waiter. I was like, ‘Live your life, but this is not Outback Steakhouse, girl.’”

When you read the rest of their dating story, you get the feeling that Billy is really not into Alyssa, and according to Twitter, he’s obnoxious.

Vanity Fair writer Maya Kosoff, who is also Alyssa's friend, tweeted to her 21,000 followers about her friend’s date.

Shortly after, Twitter chimed in, including one user who claimed to know him.

It seems like people aren’t so fond of Billy from the Upper East Side, and there might be some accuracy to him considering himself “undateable.”