The Unique Discomfort of Dating as a Xennial

The micro-generation between Gen X and Millennials is caught somewhere between the worlds of online dating and IRL romance

February 16, 2021 9:40 am
Dating on the cusp
Dating on the cusp
Rinee Shah for InsideHook

You’re out on a first date with someone, and all the hallmarks of a successful introductory encounter are there: good conversation, quick agreement on a shared appetizer, some spurts of laughter and more. Then, their phone goes off, and without hesitation, they check it.

Should such a scenario unfold in front of many Millennials, it would probably be NBD, if not completely overlooked. But for some slightly older folk, it might be taken as an annoying, passive-aggressive sign of disinterest or, worse, disrespect.

This divide represents one of the many unique challenges of dating as a Xennial — the micro-generation that rests somewhere between Generation X and Millennials. Given that categorization, says writer Sarah Stankorb, 40, who named the age group of which she’s a part in 2014, “You’re not too much one thing or too much of another thing.” 

The primary reason for this generational fence-sitting? “We grew up analog and then we lived through a technological revolution,” says Stankorb. The cohort is, thus, “adaptable,” she adds, but its members also “have living memory of what it was like before that change,” and “can imagine that maybe the way we do things right now is not always best.”

Sounds about right to me. Born in 1979, I’ve often observed stark differences between myself and people aged either just a few years older or just a few years younger than me. I’m technically part of Generation X, but I’ve never shared their emotional attachment to punk rock and new wave music — or the brooding, stiff-upper-lip disposition that accompanies such taste. On the other hand, while the eldest Millennial is a mere 11 months younger than me, I certainly can’t relate to their notoriously coddled sensibility either.

It’s like I’ve been stuck between generations, defyingly unable to fit in with two groups of people whose age gap withers with each passing year.  

The newly minted definition of “Xennial” (pronounced “zenēəl”) doesn’t help matters; its vagaries only call further attention to the micro-generation’s extraordinary uniqueness of being. After achieving sufficient ubiquity in the zeitgeist to warrant inclusion in the Oxford English Dictionary last year — the word equivalent of a doctoral degree — “Xennial” is simply defined as “a member of an age group born after Generation X and before the millennial generation (specifically in the late 1970s and early 1980s).” The publication of this scripture only intensified a web-based Cold War over the micro-generation’s age range. In her piece, Stankorb categorized Xennials as being born between 1979 and 1983. Others have since taken liberties with the threshold, expanding it to a full decade running from 1975 to 1985.

Regardless, as the years go on for Xennials, their very particular approach to life, fueled by a perpetual existence as an unknown quantity, has propagated a number of social challenges for them, which show up profoundly in the dating world.

One obvious difficulty for single Xennials — also true for aged daters of any generation — is that “the dating pool gets smaller as you get older,” says 39-year-old secretary and Oregonian Lisa Smith (a pseudonym). This is a harsher truth for Xennials than it is for single Gen Xers, because birth rates have consistently fallen since the 1950s. But as Xennials reach the point where many of our marriages are coming to an end, Smith is optimistic that more age-appropriate fish will re-enter the sea. Still, she says, “the fish that are left are those of us that have reasons why we’re single,” like “a lot of emotional baggage.” 

Also accompanying  a fresh batch of divorcees on the market? Their children, who might be part of a new relationship dynamic from jump street. That’s something 39-year-old Devon Clement, who’s single, lives in Manhattan and runs her own post-pregnancy parent and newborn care business, personally wants to sidestep. “Not because I don’t like kids,” Clement asserts, but because “there’s always drama with the ex.” 

She finds that even in palatable co-parenting partnerships — of which she’s seen many — each party is still beholden to the other to a degree, and the prospect of step-parenting, in her mind, brings “all the responsibility and none of the authority.”

“It’s just not something I want to get involved in,” Clement continues. “If I’m going to have to deal with children and they’re not even going to be my own, it’s the worst of both worlds.”

One way to avoid such pitfalls is to date younger, but that’s when the Xennial-specific problems really start to become apparent. 

Dating digitally has become the go-to for seemingly just about everyone, particularly young people. However, to Xennials, emerging college graduates at the time online dating first became widely accessible, it was viewed as a last resort. Back then, a single person turned to because they had problems meeting people “in real life.” But thanks primarily to the Millennials’ embrace of online dating and “the apps,” that’s no longer the case.

“The social norm has changed so drastically that now if you think anything negative about app dating, you kind of look like a Scrooge,” says Markie Keelan, a psychotherapist based out of the Denver clinic Growing Self, who focuses on career and romance coaching. She councils many Xennial clients, whom she says often discuss dating issues involving age gaps and digital platforms.

Keelan says if an individual has a cell phone starting at, say, age 10, it becomes a part of their life that they’re very comfortable with. But for Xennials and older people dating in this hyper-digitized world who did not grow up under such circumstances, Keelan says, “You need to be able to communicate very effectively when you’re not with that person, and effectively when you are with that person. So it takes two different skill sets now.”

Xennials remember a time when people met prospective romantic partners at bars, coffeehouses, parties, work functions, and other social gathering spaces and events. We asked them out face-to-face, and perhaps got to know them better over a phone call. But as frightful as those outcomes might sound to some whippersnappers, it was a time of arguably more effective communication. 

Today, we text, which eradicates crucial body language, voice intonations, and other non-verbal cues that delegate meaning and evolved with mankind to help us thrive. In a 2019 op-ed, psychotherapist Maggie Mulqueen did her best to tear down the texting institution, writing that the behavior is “ruining personal relationships.” According to her, it encourages passive (and sometimes passive-aggressive) behavior, along with lying. Texting also, counterintuitively, curtails conversation, and may reduce efforts toward true connectivity between people. 

Through online dating and the texting that comes with it, people are now founding relationships upon bedrocks of poor communication. The more mindful Xennial — and others who recall the before times — might not be so emphatic about such means of generating connectivity. They were just fine doing it the old-fashioned way.

“I try not to text with people until I’ve met them a few times face to face,” says a 42-year-old New Jersey man who works in the medical industry, and asked to be referred to as “Tony.” “People don’t read me well; I make a lot of sarcastic comments and sometimes [the meaning] gets lost, but in person you can figure that out pretty quickly.” 

Tony, who got divorced three years ago, and until then hadn’t been single in over a decade, uses the apps to date partly because “it’s way harder to meet people” than it was in his younger days. “People are less likely to make conversation than they were maybe in [the] 2006 timeframe when I was actively dating,” he says. 

A 40-year-old voiceover artist in Philadelphia who asked to be referred to as “Lauren D” says she started meeting people online in 2001, but has since “retired” from using dating apps. 

“Apps are poisoned with lazy ass people,” she says. “I don’t have to wish for the old days because I’m living the old days. I choose only to meet people ‘in the wild.’”

Lauren D says she has an easier time relating to Generation X people than she does Millennials and, thus, prefers to date older. That’s not the case for everyone though. Reddit user tattooed_RN, who identified herself as a woman born in 1977, told me in some forum comments that she can’t relate to men older than her because they’re too conservative. “Ideally,” she says, she tries to date the few remaining single Xennials out there.

But if a Xennial goes the other way and dives into a relationship with a younger person, again, there’s a chance they’ll be turned off by their consistent engagement with digital devices — ironically, the things that probably brought them together in the first place. This was the case in my last relationship, when I lived with a woman nearly four years my junior. I’ll always appreciate a great many things about her, but asking her to separate herself from her phone so we could enjoy a movie together was like requesting she lop off a limb. I wanted to share that time exclusively with her, not her social media followers or anyone else texting her about things that could wait until tomorrow. In those moments, connectivity with her was compromised. 

Keelan says the younger people she works with don’t complain about such actions, but when older people encounter them, she sees it create “a lot more distrust in partnerships.” 

“You start questioning your partner because it doesn’t match your comfort level with that technology,” she adds.

Exacerbating Xennial discomfort with the apps is the technology’s ability to make them seem disposable to prospective partners. If a blazing connection is not felt instantaneously by one party, with access to, in some cases, millions of other potential hookups, there’s little incentive for them to stick it out past a first date.

Tony says that when he’s dated Millennials, they seemed to succumb to what he calls “the illusion of many.” “A lot of them always seem like they’re just kind of looking for something better,” Tony says. Xennials, however, are “more interested in seeing ‘where it goes.’”

“Mindfulness can be easily disregarded in app dating,” Keelan says. Many of her clients who engage in app dating turn to the technology after a breakup or a non-connection for validation through matches. The ensuing dates — consciously or otherwise — are often arranged for self esteem-boosting purposes. “Obviously, that’s not going to be helpful,” Keelan says.

Instead, she says single people should seek a relationship, something that proves rewarding but through active partnership. If two people clearly live outside each other’s respective value systems, nixing a second date is fine but, otherwise, Keelan says, “You need to be very clear on what it is you’re looking for in a relationship. Chances are very unlikely you’re going to find that on a first date; that’s why second dates are very helpful.”

If COVID-19 has had any impact on the way we find romance, it’s been to infuse more technology into the search. A July 2020 BBC article speculates that video dating may stick around post-pandemic because it adds a cost-effective layer to the screening process, without risk of bodily harm, while stamping a relatively nominal footprint on one’s personal schedule. To Xennials and older single people, it feels like we’re being pulled further away from the dating world we grew up in.

“I went on a lot of Zoom dates; I hated them, hated them with an absolute passion,” says Tony. “It’s all the negatives of a first date — the uncomfortableness and the stress — but without any of the positives,” like subtle, spontaneous eye contact and the discovery of genuine chemistry.

But the Xennials’ noted adaptability can prove valuable in 2021 dating and whatever befalls us in the future. 

“Xennials have a really unique stance that … gives you such an advantage,” Keelan says. “You can embrace both worlds,” in real life and online dating. 

Though Devon Clement says at times she’s been down on online dating, she does appreciate the starting point it provides, giving users vital information about their matches — including their age, status and sexual preference — that a person could not decipher from across a bar. 

“I think people get frustrated with it because it’s very much a numbers game,” Clement says. “Your chances of meeting someone good are much higher, but your chances of meeting someone bad are also much higher.” To be able to wade through it all, she says, “You have to be motivated.”

But pitfalls remain for the single, mindful Xennial. Even Sarah Stankorb, Xennial god by way of nomenclature, relays stories of her Xennial friends, namely the freshly divorced ones, experiencing dating hardship in recent years. 

“It’s highly weird and uncomfortable in all the ways that you would think,” Stankorb says. “It’s not the way it used to be.”

Fortunately for her, the near middle-aged neologist herself has never personally had to confront the digital dating landmines that her contemporaries have been forced to navigate of late. Stankorb began dating her husband, the father of her two children, when she was just 19, and she says he’s “easily the only person I could imagine living with, especially through a pandemic.”

There were no apps, no texting. She met him IRL, in a college classroom.

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