Reflections from a Former Matchmaker

Tu B’Av was once a day when unwed women of Jerusalem dressed in white and congregated in local vineyards to dance in the name of finding love (also, something about a grape harvest). Since then, the day has developed into what we know in 2015 as the Jewish Valentine’s Day – a time to celebrate love in any form and any stage, while wearing any color. Still, as I think about this upcoming Tu B’Av, I wonder about those women in white.

Was their search for love really as joyous as dancing freely in open fields? Or, did they all return home from dancing with anxious, churning stomachs over whomever they did or didn’t meet that day?

The single’s search for intimacy and partnership is one I’m well acquainted with. Until recently, I worked for a matchmaking company in New York, helping searching singles across the country find love, or, at least, make their search a little more bearable. Our clients varied in age, race, nationality, sexual orientation, gender identity, and political and socioeconomic status. We knew all several thousand by face, and most by name.

There was Jim, the 22-year-old screenwriter and actual lumberjack, who needed a man who could keep up with his unpredictable lifestyle. There was Ash, the 47-year-old recent divorcee, who hadn’t been on a first date in 31 years. There was Joan, the 33-year-old marketing executive, always in silver stilettos, who was ready to settle down with a nice Jewish girl. They and thousands of others came to us with rich histories and complicated relationships to dating, looking for a new approach to meeting people.

By the time I met Angela, a ballet dancer and my very last client before I left New York, she’d been on 127 first dates in New York City. (Yup, she counted). We met in my office, and she spoke at length about the challenge of meeting people.

“When I meet someone I like, it all seems worth it,” she said, slumped over her coffee and staring out the window onto traffic and unseemly scaffolding. “But, it never sticks, and with most of my friends coupled off, my dating experience is really colored by loneliness and frustration.”

The sentiment was familiar. In my 16 months as a matchmaker, I’d heard variations of this countless times. For some people, finding a life partner is easy. They meet their person in high school, or college, or on their first-ever online date, and forever have a dancing partner for clubs and weddings and open vineyards. For others, the process of weeding through the dozens or hundreds of potential matches is a dynamic experience that can test their patience, resilience, courage, and emotional strength.

I invited Angela to our photo party that night to introduce her to new single friends. Photo parties were small gatherings in our office lounge, where attendees drank free wine and posed for new headshots. They started as a way for us to rid our files of all-too-common bathroom selfies, and soon became an unexpected haven for clients to relax with new friends, swap strange dating stories, and be comforted by a community of people who understood their experiences. Sometimes people paired off at these events, but mostly, they formed new networks of friends, who supported each other.

I watched that night as Angela connected with other attendees. Her shoulders were looser and her smile was genuine. Sure, she would feel lonely and stressed again, just as she had earlier that day. In fact, she would go on dozens of dates through the service before meeting a woman she liked enough to pause her membership. But, for a few hours that night, she was surrounded by people who understood her. She was in her own personal vineyard.

This Tu B’Av, I wish those searching for partners kehila – community – and the time and space to celebrate those who love and support us throughout challenging times. Let’s celebrate not just romantic love, but the love we share with those who allow us to restore our hope, believe in ourselves, and rejoice. Chag sameach!

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