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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

Will Gleason
Written by
Will Gleason

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

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