Skip To Content

Dating Dilemmas

Seth Weiss, 26, a consultant from Chicago, once got set up with two cousins within a two-week span.

Alison Rodin, 24, a programming assistant from New York City, once was out to dinner with four friends when it occurred to her that three of the women at her table had gone out with the same guy.

Shortly after signing our lease, my new roommate and I realized that she’d dated my ex-boyfriend and I’d dated hers.

Welcome to life on New York City’s Upper West Side, a place not unlike the Lower East Side of yore, where Jews lived virtually on top of one another in an insular ghettolike community where the synagogues, schools, pickle shops and kosher delis could all be found within a few blocks. It was a dirty and disease-ridden area, but also one that pulsated with a vibrant Jewish pride that many still yearn for today. They needn’t, though. That type of Americanized shtetl-living never really disappeared — it just moved uptown.

The squalid conditions are gone, replaced by a more hygienic region that lures thousands of young Jewish professionals each year. It’s a neighborhood where the youthful and the Modern Orthodox go to find mates. But more often than not, they just end up finding one awkward dating situation after another.

“It’s like high school all over again,” said Lucy Cohen, 25, an assistant editor. Cohen grew up on the Upper West Side, but she made a conscious choice to stay out of the local dating scene. Cohen moved south, to Greenwich Village, as soon as the opportunity arose, and recently she married a British man she met through a friend.

“But the stakes are higher,” she continued. “It’s a small, insulated world, so everyone knows everyone, and ends up dating everyone. But in high school, no one’s looking to get serious, whereas on the Upper West Side, everyone is looking to get serious. And that ends up being anxiety provoking for everyone.”

Indeed, most Modern Orthodox Jews on the Upper West Side know each other, or at least know of each other, since they attend the same synagogues, live in the same buildings and often end up at the same parties.

This situation is, to some extent, ideal, because it makes checking up on someone really easy. An enterprising suitor or suitee can usually get a person’s entire back-story in just two or three phone calls. It’s somewhat less than ideal, however, when a first date becomes a last, or when a couple breaks up.

One woman I spoke with lives down the hall from her ex-boyfriend, who happens to also be the ex-boyfriend of one of her best friends. Another got set up with a guy the same week one of her good friends was asked out by that same guy.

The Upper West Side is rife with these kinds of thorny, semi-embarrassing tales, which are told at the Shabbos table each week.

“I choose to stay out of the fray, because the atmosphere’s crazy,” said Rosy Zion, 27, a lawyer from Brooklyn who’s been living on the Upper West Side for two years. “It’s like survival of the fittest up here. Girls are going after limited resources — the nice Jewish boys,” she said with a laugh.

Unlike Zion, most people up here find themselves enmeshed in the area and all it offers, and simply hope that each slightly sticky dating situation will turn out to be but a mere pothole along the seemingly endless road to happy coupledom.

In fact, after the aforementioned Weiss realized middate that he’d already set up another date with the girl’s cousin, he thought he’d blown things completely and found himself more relaxed in her presence.

“I figured there was no chance I could really go out with her again,” he said, “so I kind of lost those normal nerves that occur on a first date.”

They ended up going out for two months.

That girl’s married to someone else now.

Someone she met on the Upper West Side.

Someone I used to date.

Leah Hochbaum is a freelance writer living in New York.

I hope you appreciated this article. Before you go, I’d like to ask you to please support the Forward’s award-winning, nonprofit journalism during this critical time.

Now more than ever, American Jews need independent news they can trust, with reporting driven by truth, not ideology. We serve you, not any ideological agenda.

At a time when other newsrooms are closing or cutting back, the Forward has removed its paywall and invested additional resources to report on the ground from Israel and around the U.S. on the impact of the war, rising antisemitism and the protests on college campuses.

Readers like you make it all possible. Support our work by becoming a Forward Member and connect with our journalism and your community.

Make a gift of any size and become a Forward member today. You’ll support our mission to tell the American Jewish story fully and fairly. 

— Rachel Fishman Feddersen, Publisher and CEO

Join our mission to tell the Jewish story fully and fairly.

Republish This Story

Please read before republishing

We’re happy to make this story available to republish for free, unless it originated with JTA, Haaretz or another publication (as indicated on the article) and as long as you follow our guidelines. You must credit the Forward, retain our pixel and preserve our canonical link in Google search.  See our full guidelines for more information, and this guide for detail about canonical URLs.

To republish, copy the HTML by clicking on the yellow button to the right; it includes our tracking pixel, all paragraph styles and hyperlinks, the author byline and credit to the Forward. It does not include images; to avoid copyright violations, you must add them manually, following our guidelines. Please email us at [email protected], subject line “republish,” with any questions or to let us know what stories you’re picking up.

We don't support Internet Explorer

Please use Chrome, Safari, Firefox, or Edge to view this site.