A Bunch Of New York Women Went To Silicon Valley To Find Millionaires And Ended Up In Tears



Screenshot via Crowdtilt/ The Dating Ring

Screenshot from The Dating Ring's promotional video.

Getting shipped across the country to find a millionaire husband and explore a new city may sound like an exciting adventure.


But not every aspect of the trip was as glamorous as it seems.

NYMag writer Maureen O'Connor was among 16 women chosen to participate in "Cross Country Love: Help Fly NYC Women to SF."

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The five-day trip, which was crowdfunded via Crowdtilt, was thrown by Lauren Kay, the founder of dating startup The Dating Ring. The idea behind it is that Silicon Valley has become so dominated by wealthy men that it has caused a supply-demand imbalance. For some reason, this can only be solved by flying women from New York to San Francisco. Naturally, the concept is not without its flaws.

Nonetheless, women interested in attending the trip had the option of choosing different packages that include an allotted number of dates, admission to a cocktail party, flight and housing. These options range between $500 and $1,250.


The dating service was initially launched in New York City, but it expanded it San Fransisco after the startup was accepted into Y Combinator.

O'Connor detailed her experience in what at first appeared to be a college-style five-day sorority retreat. She described bonding with the other ladies on the trip, attending swanky cocktail parties, making new friends, and meeting interesting men.

But things took a slightly darker turn toward the end of her narrative.

On the third day, O'Connor and the rest of the New York gang headed to a party thrown for the Crowdtilt benefactors.

"Some of the men at this party are more eccentric than those we received as matches," O'Connor recalls.


One programmer who donated several hundred dollars to the campaign compared the situation to giving money to a homeless person-implying that it was a demeaning act of pity.

He then criticized the online dating scene, saying that he prefers to "use reality" as his platform, and began to touch O'Connor.

Here's how O'Connor described the rest of her experience at the party:

As the party grows, we become inundated with men. We are experiencing gender imbalance in the wild, and it is chaos. Every time I turn, there are men lined up waiting to deliver carefully rehearsed greetings or to initiate repartee.

The next day, O'Connor sought out some weed brownies for her and the rest of the ladies on the trip. By midnight, half of those girls ended up crying in the fetal position, with O'Connor comforting one of them by stroking her hair.


Kay's cross-country matchmaking endeavor had been met with criticism ever since the Crowdtilt campaign launched in March.

Valleywag likened the idea to the comfort women of "imperial Japan," and commenters under the promotional YouTube video slammed the idea. One commenter even called it "just plain embarrassing and gross."

Here's the promotional video that helped The Dating Ring raise more than $10,000. Check out O'Connor's detailed account for the full story.