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An Evening with a Wingwoman

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Since Nate got married—and Steve, and Jake, and Todd—we decided the time was right to check in on the Wingwomen service, which just recruited a fresh crop of beauties to "wing" for the gentlemen of New York (so much responsibility). We sent our UD field correspondent out to test the effectiveness in an uncontrolled environment. What follows is his complete report.

9:05pm: On a rooftop bar, meet Wingwoman, Anika. Cute and bubbly blonde.

9:28pm: Overcome with concern. Guy-girl ratio is roughly that of an all-boys school. Anika isn't worried, quizzes me on type.

9:43pm: Anika heads to ladies room, employs patented move: While primping, she compliments woman next to her on bracelet. The idea is to bond, then introduce me later. The woman, a bathroom attendant, is not impressed.

10:05pm: Anika spots a fetching pair. Before I've sat down, Anika has found out their jobs, favorite hobbies and astrological signs.

10:09pm: The better-looking of the pair mentions a boyfriend. Anika and I immediately disperse.

10:33pm: Anika sniffs out another pair. Voluptuous brunette. Gorgeous blonde. We sit on a nearby bench and wait. "Something will come up," Anika says. "It always does."

10:37pm: Anika asks blonde about blanket she's clutching. The two talk blankets for good five minutes, giggle profusely. Astonished, I vow to improve my blanket small-talk.

10:42pm: Anika shrewdly steps away. I slide closer to gorgeous blonde, procure vitals: Courtney, consulting, no boyfriend.

10:55pm: Anika returns with drinks. I scribble in notebook: "true pro."

11:17pm: After hearty group laugh (blanket joke), Courtney's friends say they're leaving and begin pulling her away. Phone numbers are quickly requested...and exchanged. "Look forward to your call," Courtney tells me, flashing sexy smile.

12:00am: Anika walks off into the darkness. What a woman.

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