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Is Being Single a Long Time Really the Red Flag We Think It Is?

Or is the bigger problem the people who jump from relationship to relationship with no time for themselves in between?

I’m not sure how long is too long to be single, but I suspect I surpassed the time limit somewhere around the three-year mark. Whenever the question comes up on dates, I answer honestly, and dudes look at me like someone has died. I feel less like a single person and more like a haunted Craigslist apartment. 

The question originates from a constructive place; it’s an extension of the timeline for how long it should take to get over a failed relationship. “There is a lot of validity to the timeline of getting over a breakup in half the length of the relationship,” Elisabeth Goldberg, a marriage and family therapist, explains. “If anything, it’s a goal to work toward when someone feels they’ll never get over it.” But once they’ve hit that threshold, they can experience pressure to prove they’re really over it by moving on with someone else. And when they don’t, and stay single, they’re often hounded to explain why. 

All of this really depends on how you define dating versus being single — a distinction that’s become increasingly muddied among millennials; many of us admit to never being in a formal relationship, instead opting for multiple casual flings. Erica Spera, a comedian and host of the dating podcast Shooters Gotta Shoot, refers to these semi-relationships as “sneak peaks.” And if she doesn’t count them, the 29-year-old has technically been single since high school. 

Spera suspects that if we grew up in our parents’ generation, these relationships would not only count, they’d likely last longer. “There wasn’t this ‘are we exclusive’ bullshit; it was like, ‘When you’re dating someone, they’re your girlfriend,’” she says. Back then, if you were single for 14 years, that would imply you didn’t even go on a few dates with anyone at all during that time. Now that the criteria has shifted to having an established commitment, larger breaks between relationships should be more socially acceptable than they are. “If you go by the official title, it’s very normal to go a long time being single, because we’re not counting these mini relationships in between,” Spera argues. 

Spera’s podcast co-host Molly DeMellier, 28, was single for eight years up until recently. She and Spera started the podcast because the two former NCAA athletes were successful at shooting their shot in all areas of life — except for dating. So they began reading self-help books and interviewing experts to try to figure out why. When DeMellier entered into a new relationship in quarantine, she found herself trying to speak to the gaps in her relationship history. “The first time I said, ‘I don’t really date or have relationships,’ he was just like, ‘What do you do?’” DeMellier tells me. “I don’t know, man.”

This happens to men as well. The older he gets, the more Blake Harper, 28, has to explain why he’s been single for nearly three years. He’s found that it’s been easier to convince women that the gaps in his dating resume are healthy, but it’s been a much tougher sell for his Christian family. “My grandma tried to set me up… in a pandemic,” he says. His family sees him being in a relationship as an adult achievement on par with having a good job — a necessary box to check for being a successful person. 

“When my grandparents talk about me, it’s not very nuanced. It’s more like, ‘Does he have a wife? No? He needs a wife,’” Harper explains. Still, he sees these longer breaks between serious girlfriends as a sign of growth. “I’m smarter about it now, that’s why I have shorter relationships,” he says. “It only lasted two months because that’s how long it took to realize I didn’t want to waste their time. That should be a good thing.” 

Dating experts definitely think it is. In fact, they believe it’s more of a red flag to jump from relationship to relationship than it is to be single for a long time. Monique Kelley, author of the blog Confessions of a Serial Dater in L.A., explains that going from one relationship to the next sends a message that “you don’t value the true meaning of a significant relationship.” “It also means that you have areas that need to be addressed, and you’re seeking validation from the outside instead of looking within,” she continues.

On the other hand, she admits, “There comes a point when you get stuck in your ways” as a single person. “They put the blossoming relationship on the back burner or squeeze in time instead of prioritizing the possibility,” she says. Other bad habits include staying in contact with toxic exes, making excuses for being single and a general discomfort with being vulnerable.

Time management is the most practical challenge when it involves getting back into a relationship after being alone for a long time. “Being independent is very different from being coupled in a daily relationship,” Tammy Shaklee, founder and president of the LGBTQ matchmaking company H4M, says. Understanding each person’s attachment style and love language can help potential couples move beyond this, but it’s usually an uncomfortable transition.

More so than being single itself, the insecurities that develop from being alone for a long time can sabotage new relationships. The best way to prevent this from happening? Stop counting the years. “Who cares how long it’s been that you’ve been single? Let go of the calendar and timeline,” Shaklee recommends.

Along those lines, I’ve decided to take Shaklee’s advice and abandon my search for a single expiration date. So far, it’s made me more consistent with my standards, as I no longer waver on them because I’m worried that it’ll make me single for yet longer still. In turn, dating has become less anxiety-provoking and more fun. And so, the next time a guy asks how long I’ve been single for, I’ll inform him that I stopped tracking my alone-iversary — and assure him that it’s the normal amount for a haunted, mid-30s millennial.

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