Jun 05, 2014

One Woman’s Experience Flying Cross-Country In Search Of Love In The Land Of Startups

Travel and romance are not mutually exclusive activities. As a...

One Womans Experience Flying Cross Country In Search Of Love In The Land Of Startups

Travel and romance are not mutually exclusive activities.

As a matter of fact, one often leads to the other. That combination of foreign air with the typical time constraint of a trip seems to often inspire butterflies and googly eyes worth writing home about.

But, last week, The Dating Ring took this natural pairing of new places and new faces a step further by flying single New York women across the country to date single men in San Francisco.

So, here’s the premise. The Dating Ring is a startup matchmaking service, initially launched in New York City. When the crew earned a spot in Y Combinator, they expanded out West.

Lauren Kay and her co-founders noticed something on both coasts: a serious imbalance in the single sexes. The New York pool had two women for every man. In San Francisco, almost the opposite was true with three men for every two women. Bringing the two, romantically frustrated populations together for dates seemed a little crazy at first.

But, “make a joke 10 times and it becomes a Crowdtilt campaign,” Kay was recently quoted as saying in The Huffington Post.

So, Crowdtilt they did, and with $10,222 raised, the ladies were gathered and the trip was set in motion.

Since the initial planning, there has been some ugly press surrounding the project — press that isn’t worth quoting here. But, let’s just say the presumptions made about the women going would make my father very angry.

Trolls will be trolls, but as an avid traveler and adventurous kinda gal, I’d like to highlight the real motivation of this trip, and a valuable experience worth shedding light on.

We did not fly to San Francisco to bag ourselves some nerdy millionaires, or to offer some charitable companionship to “undatable techies.” It was not a last-ditch effort of bitter, single women, fed up with the men that make up their own zip code.

Dating is frustrating as Hell, yes, but committing yourself to exploring a new city for love shows an optimism towards dating that’s pretty rare these days. We were open to possibilities.

These women were all impressive, inspiring figures whom I was thrilled to call friends by the time our weekend wrapped up. There was a firefighter, a speech therapist, a medical student, a life coach, an actress and a writer, among others, who each impressed me in their own unique way and made me feel a little better about being single myself.

There was nothing desperate or dirty about this trip. It was simply a group of women, willing to have an adventure, think outside of the box, and put themselves out there in a new place for the possibility of a little romance.

And you know what? As a social experiment, it was not only fascinating, but successful for some as well.

One Womans Experience Flying Cross Country In Search Of Love In The Land Of Startups

As the coupling of East Coasters and West Coasters unfolded, the cultural clichés of our two cities were front and center. The pervasive tech scene of San Francisco became a running joke among the girls as each and every date would cite the startup they currently worked for. And when half of us arrived at the bar wearing black leather jackets and commanding conversations with Big Apple flair, I was repeatedly told that our “New Yorkness” shined through.

Each side had their frustrations with dating. San Francisco men claimed a shortage of females in the male-dominated technology industry that ran the social scene. Our New York contingent spoke of men who can’t commit, thanks in part to the tempting array of options provided by the country’s largest city.

But we all had one thing in common: Dating is getting harder for everyone, it seems. The game is changing, the rules are shifting, and in the age of digitized social lives, people are increasingly lonely. Meeting all of these new people in person was at the very least, a refreshing escape from the online options that dominate our lives on both coasts.

Cultural caricatures and dating frustrations aside, many of the matches worked out.

One of the ladies regaled us with the story of a kiss beneath the Golden Gate Bridge and plans to spend the next day with her date and his friends at a food truck festival.

Another girl beamed into her cell phone, struggling to describe her new crush as she furiously texted while we played tourists at Pier 39.

On the final night, there was a romantic drive to the mountains for one lucky lady, and a butterfly at the window to wake her up the next morning. It was a San Francisco Fairy Tale that we all fell for as she glowed on our picnic blanket in Alamo Park, reliving the story, detail by romantic detail.

As for myself, I had some great experiences through the dates orchestrated through The Dating Ring in San Francisco. But, ultimately, I bailed on the last party — exhausted by the cameras covering the trip for Nightline and the curated conversations surrounding every drink. I joined two of the girls in calling a Lyft car and headed to a local beer bar in the Mission District. Moments after arriving, I was making eye contact with a curly-haired guy playing pool.

“You’re too Springy for San Francisco,” he said as he approached me at the bar.

Glancing down at my exposed mid-drift, I had to agree. In New York, I may have been taken aback by his bluntness, but in this new city, I was charmed by his honesty. And with the surprisingly chilly wind outside, my outfit was definitely that of an out-of-towner.

I left that night with his number and an invitation for sushi the following day.

“It’s the right coast for raw fish,” he assured me.

Maybe it was the thrill of seeing a new city with a new acquaintance, or maybe it was just a coincidence that I would hit it off with someone on a trip specifically designed to pair me with someone new. But, whatever it was, it felt right, and I left San Francisco with exciting possibilities that no tasteless criticism will ruin. I can do that myself if it comes down to it.

I’d like to think this whole experience does not illustrate a desperate dating landscape for New York women who are forced to fly all the way across the country to meet men.

On the contrary, it proved that although dating has changed and been complicated by the influx of digital options and the waning efforts to meet each other in public, putting yourself out there (yes, way out there, even) can really pay off. In a city where everyone is creating new technology and tech companies are computerizing the most mundane aspects of our lives, a fresh perspective can still inspire two people to exchange numbers in a bar.

Travel inspires us to do so much, and this time, it inspired me to invite a certain someone to come experience my hometown next.

One Womans Experience Flying Cross Country In Search Of Love In The Land Of StartupsBritany Robinson is freelance travel writer and blogger who periodically calls New York City home. She writes about her adventures, at home and away, on her blog, Stars on the Ceiling. This fall, she’ll be hitting the road for her project, Road Trip Home, USA: The Millennial Traveler’s Guide to Settling Down, through which she’ll explore the country in search of cities that appeal to her generation — and maybe even find one to call home next.

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