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Meet the Undateables: Joshua and Sasha

Jillian Anthony

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:
Joshua: He’s really picky
Sasha: Hasn’t found someone he has real feelings for in a while

Ideal date:
Joshua: Grabbing a sandwich and walking around—something simple and easy
Sasha: Taking a flight to the Grand Canyon with a bottle of chianti and watching the sunset


First impression
Joshua: “He was very handsome and had a really nice presence to him. He comes off as being a very nice person; there was no pretension there.”
Sasha: “He was a super handsome guy. I saw him sitting at the bar, and he seemed a bit shy and closed off, but at the same time it was a very nice impression.”

Joshua: “He’s very idealistic, in a good way. He has a good outlook on things. I, of course, am really jaded. He’s from Eastern Russia, so it was interesting to see his perspective.”
Sasha: “There was one beautiful moment. He asked what my favorite song was, and it was actually playing on the piano (Sting’s ‘My One and Only Love’). It was romantic.”

Awkward Moment
Joshua: “He ordered a lot of food. I unfortunately wasn’t feeling that great, so I didn’t eat that much, so I think that might have been a little awkward.”
Sasha: “I tried to lean in and kiss him, and he was not sure what I was doing. Can you imagine the worst When Harry Met Sally–style first kiss? I was like, This is my life, goodbye.”

Joshua: “I told him, ‘I have to go home now because I’m not feeling well.’ He was going to kiss me good night, and I kind of stopped him because I didn’t want to give him what I had
Sasha: “He asked if he could have my phone number, and I said, ‘Yes, of course.’ We actually texted each other right after the date. He said, ‘Hey, why don’t we meet this weekend?’”

Joshua: ♥♥♥♥ “He is an amazing person and a genuinely nice guy, which is rare to find in New York, especially among gay men. I’m going to see him this weekend.”
Sasha: ♥♥♥♥ “There was chianti but no Grand Canyon. I think it was a beautiful date. He’s such an amazing guy, and I look forward to seeing him again.”

Our daters went to Campagnola (1382 First Ave, 212-861-1102)

RECOMMENDED: See more Undateables

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