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Meet The Undateables: Anne and Chris

Will Gleason
Written by
Will Gleason

Each week, we take two New Yorkers who swear they're totally undateable, and put our matchmaking skills to the test. Afterward, we find out what went well on their date, and what went horribly, horribly wrong.

Why they're single:
Anne: She hasn’t fallen in love again after a breakup.
Chris: He has a history of bad investments that has shaken his self-confidence in finding the one.

Ideal date:
Anne: Going to see the Christmas lights in Dyker Heights, Brooklyn, with a spiked beverage in hand
Chris: A weird but good movie and grabbing drinks after to discuss


First impression
Anne: “He was there a few minutes before I walked in, and he seemed approachable and warm right off the bat. I thought he was boyishly handsome and very friendly.”
“When she got to the table, I was relieved that she was very pretty and had a nice big smile and was easy to talk to. There were no awkward pauses or anything.”

Anne: “We had some chemistry. We definitely had a lot more in common than I was expecting, and we both seemed pretty easygoing and had a similar sense of humor.”
“I definitely got a good friend vibe and could see it turning into a romantic vibe. We quickly bonded over the situation and weren’t taking it that seriously.”

Awkward Moment
Anne: “After dinner, we went to a show a few blocks away that had full-frontal nudity. Chris started snort-laughing during it, and people turned around and shushed us.” 
“[At the show later] there was a moment when a character showed his penis. She craned her neck to see it and then burst out into laughter and got shushed in the theater.”

Anne: “We grabbed a few drinks after the show and really bonded. Then we took the same subway home. He asked for my number and gave me a hug. There wasn’t a kiss.”
“We said goodbye in the subway on the platform. We didn’t do the kiss, we just hugged. It was a first date, and I had to run and catch the train, so it just didn’t happen.”

Anne: ♥♥♥♥ “I took away a heart because he didn’t try to kiss me, but it went much better than expected. I didn’t have high expectations for this, and I was pleasantly surprised.”
Chris: ♥♥♥♥♥ “Considering this was pretty much the best-case scenario for a blind date in 2017, I’d give it a five. Great chemistry, plenty of laughs, no murder attempts.”

Our daters went to Virgil's Real Barbecue(152 W 44th St, 212-921-9494)

RECOMMENDED: See more Undateables

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