Worldwide icon-chevron-right North America icon-chevron-right United States icon-chevron-right New York State icon-chevron-right New York icon-chevron-right Meet the Undateables: Meredith and Craig

Meet the Undateables: Meredith and Craig

Each week, we take two New Yorkers who swear they’re totally undateable, and put our matchmaking skills to the test

Undateables 1140

Why they’re single:
Meredith: She finds it hard to make a true connection with people using apps.
Greg: He can sometimes get nervous when he’s around women.

Ideal date:
Meredith: Seeing a movie outdoors
Greg: Walking around the city


First impression
Meredith: “I was there first, and the waitress brought him over. He seemed easygoing but kind of nervous. I think his nerves made him talk less, whereas mine make me talk more.
Greg: “She was very friendly and outgoing. We just started talking right away. She probably wasn’t someone I’d normally date, but I liked her personality.

Meredith: “There weren’t crazy fireworks, but the conversation was nice. A few stars were out, so we popped outside for a bit to sit by the rooftop pool.” 
Greg: “I think there was a little chemistry but probably not enough to go on a second date. It just felt friendly—she was really bubbly. We talked about everything.

Awkward Moment
Meredith: “I asked him what he thought about Trump, and then I was like, ‘Ugh, no. That’s the one thing I shouldn’t get into. Now’s not the time to go off on another rant.’
Greg: “She’s not a big fan of Pete Davidson, which I thought was odd. She doesn’t think he’s as funny as other people. I really like Pete Davidson, and she was a little critical.

Meredith:He was really cute and walked me 90 percent of the way home after we left the rooftop. Then he gave me a hug and a kiss on the cheek, and we exchanged numbers.
Greg: “I walked her most of the way to her apartment. My phone was dead, so I gave her my number, and we hugged goodbye. I wouldn’t say no to a second date.

Meredith: ♥♥It went really well. I’d be down for a second date to see if he was maybe less nervous. I felt like I was talking a lot, but I’d love to get to know him a bit more.
Greg: ♥♥It was a very good time. I was thinking it was going to go horribly. I would never go on a blind date normally, so I was pleasantly surprised.

Our daters went to Jimmy at the James (15 Thompson St,

RECOMMENDED: See more Undateables

Want to be set up on a free blind date? Email

More to explore