The Art of Being Single

Not a lot of people believe it until my friend Carissa flashes her I.D. and a bare wedding finger. It happened last November. Some of us kept our distance when the moment to blow out the candles came, because, I don’t know, it felt like that’s when weird stuff usually happens in movies. It was before the pandemic, so we did not award her the luxury of an extra year. Then, the clock struck 12 AM. I watched her turn forty, single, and not explode.

Despite Carissa proving the unimaginable, most singles, especially women, still live their life like time is running out. 

In fact, she once emphasized that there’s a reason restaurants don’t offer tables to accommodate one person. “Just for you” she lamented, discouraged by the semantic shortcomings never placed on couples or groups. “Just, like if I am not enough to occupy a table.” Her worst-case scenario used to be reaching forty without finding the fairytale happily-ever-after.

Take my friend Marie for example. Like Carissa, she escaped from a small town to a big city with the hopes of reinventing herself. When Marie’s husband had an affair in their home in Los Angeles, she bought a plane ticket to New York. The first thing that she did was get bangs but hit a wall of frustration when the new hairdo failed to attract a new hubby. Marie used “moving on” and “meeting someone” synonymously. Hence, the beautiful new life that she envisioned in the city that never sleeps was suddenly snoozed. 

Perhaps, the issue rooted in the pressure that she felt to start over as if ending her marriage, liquidated her former existence. Couples wouldn’t be thrown into such a severe identity crisis post-breakup if they had treated singlehood less like a phase. A partner should add excitement and fulfillment but never be the source of it. 

The clock starts ticking for many when reaching their mid-twenties and early thirties. It’s like the future is an atomic bomb that can only be diffused by finding a partner. In New York, however, this is less the case. Newbies might claim to date one person in a city of millions is complicated. Veteran New Yorkers know that’s only because it can be so damn easy to be single. The feeling of impending doom that happens when you’re still dating at an older age is absent in most folks. Plenty celebrating turning thirty, forty, fifty, and so on, still single, without combusting. 

After planning over 500 engagement proposals nationwide for the past four years, I’ve learned that love doesn’t depreciate with age. The women (or men) saying “Yes!” looked equally dumbfounded with happiness at twenty-five or sixty. The biggest difference? The older couples had more disposable income. This time crunch that singles create for themselves is actually detrimental to realizing their dream romance. That is unless parents will be helping with an engagement ring and the financial chaos that is a wedding – don’t forget the honeymoon. More than that, the younger clients were more likely to request for cliches – definitely roses – while the more mature ones focused on meaning. When you know yourself more, it’s easier to understand other people. 

New York truly empowers the beauty that comes with aging, and the strength that comes with being unabashedly self-sufficient. Disney’s saturated propaganda of happily-ever-after only works because the characters cease to exist after the movie. Real people still wake up the next morning, so why deal with being kissed by the morning breath of someone mediocre? (Or worse, the awkwardness of being a repeat client of an engagement planner.)

For singles living in cities that view marriage and raising children as the meat and potatoes of what is considered adulthood, New York offers a Neverland where “growing up” is optional. There’s a reason apartment shares continue to be universal, regardless of age. (It has been dubbed by Forbes as the real estate “Single’s Tax” due to the high cost of rent that single New Yorkers pay compared to couples splitting costs.) A lease with a roommate comes without the clause of forever. 

Settling used to make sense, because a relationship was the bridge for sex, or a family, or a particular lifestyle, etc. Then Sex and the City premiered, inspiring girls and gays everywhere. Women no longer choose husbands like careers. Likewise, men don’t need to be in a relationship to have sex every day, another benefit of feminism. The decades-long march towards gender equality has made any pressure (ok, not the green card) to tie the knot, besides love, obsolete 

Dr. Justin Lehmiller, author of the book Tell Me What You Want, found that what singles want no longer begins with getting married. A research fellow at the Kinsey Institute, he discovered that “the marriage rate in the U.S. recently reached a record low, and the average age of first marriage has increased significantly. Whereas the average age of first marriage used to be about 20, it’s now closer to 30. Today, marriage is less of a priority for adults than it used to be. While most people say they want to get married, their standards for it have increased, and they’re willing to wait longer to get what they want.” 

At last, our betrothed friends can stop walking around with survivor’s guilt, and stop offering to set us up with anyone available with a heartbeat. God forbid we arrive with a rando to their wedding. It’s not that one-night-stands didn’t exist, but sex wasn’t so readily available like takeout Chinese. Apps like Tinder changed the guidelines to what is considered safe. The most dangerous component to the childhood warning of a stranger-inviting-you-inside-a-van scenario turns out to be that he didn’t mention a drink first. For some, it’s the absence of a bed. 

Like Dr. Lehmiller says, “Whereas people used to perceive singles as deficient compared to married people. They now perceive being single as having some unique advantages, but marriage as having other advantages. Something interesting I’ve seen in the research is that attitudes toward singlehood have become more positive in recent years.” 

But while modern times empower individuals to feel complete while alone, the aftertaste that it’s not enough becomes palpable when returning to our hometowns. It’s what makes New York so unique. It’s one of the few cities where it’s common to hear forty-year-olds seriously contemplate the possibility of wanting to settle down in the future. “Maybe, I’ll even want kids,” they might say, more like a novelty than a craving. It’s possible to be kind and selfish here. 

New Yorkers are too practical to be hopeless romantics, especially when discovering a potential “the one” lives across town. Ranking 180 U.S. cities across 35 key indicators of dating-friendliness, WalletHub placed New York at No. 35, still high but much lower than researchers expected. Isn’t solitude a better alternative to transferring trains during rush hour? Love isn’t valued less, but it’s not considered the only means to achieve personal fulfillment. It’s less a milestone and more just something amazing that happens, or doesn’t. 

On WalletHub’s rankings, the city took the top spot for fun and opportunity. It’s not the promise of romance but the likelihood of adventure that makes it the best city in the world. Someone in a relationship can live an exciting life, but if anything can happen, wouldn’t those, without the responsibility of reporting to someone, be better adept for spontaneity? While many singles choose to use the time that they would allocate to a partner into actively searching for one. More often than not, New Yorkers opt to invest it back in themselves. The art of being single truly depends on how you take advantage of the fruitful autonomy that comes with it. Whether it’s kissing a stranger, or taking a book to lunch. 

Everyone should invite themselves to be single occasionally, even if just for the evening. Go to a museum, watch a show, take a class, or spend a night at home doing nothing at all, but learn to tolerate your own company before someone else’s. My friend Carissa realized she was wrong about restaurants not catering to singles. Why else have chairs surround the bar and, typically, some cute, charismatic bartender? It’s also helpful to have the option of a table for when the only conversation you want to entertain is ordering another glass of wine. New York invites singlehood with the same etiquette that she welcomes everyone, with indifference. 

Plans for the future shouldn’t be made with such a strict timeline, because you’re at risk of putting a lot of precious moments on hold when an engagement ring is still missing. I’d like to travel more, get a bigger apartment, learn a new language, but all after “Chad” proposes. Life doesn’t work this way, especially when you’re still using placeholder names for the love of your life. 

cover photo courtesy of Men’s Health

About author


Jamie Valentino interviews celebrities and tastemakers in New York City. He serves as POP Style TV's correspondent at New York Fashion Week, Tribeca Film Festival, International Emmys, and other high-level media events. You can also see his work in WIRED, VICE, Houston Chronicle, Xtra Magazine, Canadian Business, among others.
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