8 New Yorkers Who Nearly Convinced Me Love Was Dead

Illustrated by Sydney Hass.
Dating in New York City is not a game for amateurs. Like any sport, it requires appropriate attire (a.k.a., an outfit that makes you look better than Amal Clooney), a strategy (developed over brunch with your friends), and a coach to keep you sane (your best friend, your roommate, or a trusty colleague). And, sometimes, if your pals become sick of hearing your dating woes and horror stories, you take drastic measures: You hire a recruiter — that is, a matchmaker.

Last year, I took on the interesting role of professional matchmaker, searching the city for eligible singles to set up with my clients. The job was incredibly intimate; I spent hours each day asking strangers prying questions about sexual attraction, commitment issues, infidelity, and painful heartbreak. Some people were a joy to work with. Others were lonely, bitter, and desperate; with their approach to dating, they're bound to be single forever.

See, I’m an optimist. I really want to believe that there's someone out there for everybody. But, these eight people managed to challenge my faith in love. If you're not coupled up this Valentine's Day, don't mourn your loss. Life could be worse — you could be dating one of these duds.