Ross Tipograph

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.   Photographs: Kelsey Dubinsky   Why they're single: Alyssa: She has a unique sense of humor and sometimes gets nervous around new people.Emily: She's picky with personalities and wants someone strong and complementary. Ideal date: Alyssa: A movie or dinner before a stroll around the city if the weather is niceEmily: An amusement park with a pocketful of quarters for rides and games   THE DATE First impression Alyssa: “I got there early, and she came on time. Right off the bat, she was very friendly and talkative; she made me feel very comfortable. Conversation started flowing.”Emily: “She was really cute, which was nicely surprising. I greeted her with a hug while she was seated, so it was a squat hug. We laughed about blind-date awkwardness.” Chemistry  Alyssa: “I would say it was friendly. We connected over movies and TV shows like Buffy the Vampire Slayer and discussed our past experiences. A lot of good convo topics went around.”Emily: “We bonded for sure. I don't know if it was romantic; it was more getting to know each other. Some topics took her out of her comfort zone, but it wasn't bad by any means.” Awkward Moment Alyssa: “The couple next to us engaged in some heavy PDA. They were just all over each other. At one point, Emily and I thought they were vid