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:
Phil: He hasn’t been looking and can self-sabotage.
Leyth: He moves around a lot, and meets too many actors in New York.
Phil: Dinner and drinks, followed by a street fair
Leyth: Going to a museum and then dinner
Phil: “He was definitely my type. I thought he was tall, dark and handsome, and he looked vaguely familiar. Later, we found out he was in grad school with a friend of mine.”
Leyth: “Immediately, I thought either I was overdressed or he was underdressed. He wasn’t my type, but he seemed approachable, down-to-earth and very free-spirited.”
Phil: “We got along well. It seemed like we vibed. If we hung out again, I could see it maybe developing into something more or maybe just a close friendship.”
Leyth: “No romantic chemistry at all—I’m sure you hear that a lot—mostly because of small nuances. Like, he referred to himself as ‘she’ and ‘girl.’ I’m not into that.
Phil: “I have a habit of over-apologizing, and it’s so bad I don’t even notice it. He called me out on it, then I apologized for apologizing. It’s something I’m working on.”
Leyth: “I laughed really hard at one point and blew out a candle, so they had to relight it because of my obnoxious laugh. After that, we kind of moved it to the side.”
Phil: “We walked to the train together. He was heading uptown, and I was heading back to Brooklyn. He asked for my number and said he’d love to see me do stand-up.”
Leyth: “We hugged and said goodbye. I don’t think we’re gonna text, but I said I’d love to come to one of his shows. He was so nice, the kindest person.”
Phil: ♥♥♥♥ “He was fun! The only thing that would have made it a five out of five is if he took off a mask and told me he was Troye Sivan. Surpassed my expectations.”
Lyeth: ♥♥♥♥ “Great dinner, great company. We actually talked about substantial issues—just no sparks, except for the lighter they used to relight that candle.”
Our daters went to Mr. White 212-510-7229, 123 St. Marks Pl)
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