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How Long Should You Date Someone You’re Only Kind of Into?

Being ‘meh’ about a person you’re dating might say more about you than it does about them

At this point, I’ve written about my romantic failures enough to recognize that I’m at least the common denominator, possibly even the problem. Though my intimacy issues are vast, friends, therapists and exes have all described me as “emotionally unavailable.” And so, I date equally emotionally unavailable men — a truly abundant natural resource — in order to not have to deal with making a decision.

Occasionally, an emotionally available dude sneaks into the mix, and I have to either run away or face my bullshit. But availability doesn’t always equal compatibility, as I learned last fall after powering through a casual, 90-day cuffing-season relationship with a nice-enough guy. I was attracted to him and we had fun hanging out, but he didn’t allow his dog on the couch. It might seem like a trivial, Seinfeldian-esque gripe, but I strongly believe dogs belong on couches and this felt like a symptom of many other fundamental differences. By the time he finally said we weren’t compatible over leftover Thanksgiving pie, it was one of the few things we ever agreed on. 

As much as the relationship felt like a giant waste of time, dating experts contend that singles typically spend anywhere from three to four dates — or to two to three months — trying to figure that out. Other research suggests that the three-month mark is when most couples say “I love you” and commit to being exclusive. However, Selena Coppock, comedian and creator of the parody account @NYTvows, recommends an expedited approach. She usually gives it three dates; if she’s still not sure, she tries her “three beers on an empty stomach test.” ”If I didn’t want to make out with him after three beers on an empty stomach, it was never going to happen,” she tells me.

Tammy Shaklee, founder and president of the LGBTQ matchmaking company H4M, recommends four dates — and no booze. “Anthropologists have said it takes four good dates when you meet someone new to even begin to determine if they could be in your future,” she explains, noting that these need to be diverse, active dates, not just dinners, to see if there’s a potential lifestyle match.

Another challenge, she adds, are the two conflicting theories at play: One says we’ll “just know” when there’s a spark; the other claims initial chemistry is overrated and real romantic love develops over time. Confusing matters further, there’s truth to both ways of thinking. “Rom-coms, Disney and Hallmark have ruined us all to a degree,” Shaklee says. “What feels good initially will still take work in the duration. It’s sometimes hard for results-oriented singles to be patient and recognize a ‘slow burn’ when meeting someone new. It’s not all immediate connection, spark and chemistry when two new singles are introduced.”

According to breakup coach Paige Wilhide, adults typically fall into one of four categories of attachment styles — avoidant, anxious, secure and disorganized — which dictate their behavior in relationships. “Avoidant people tend to leave too soon or shut down when the talk of commitment comes up. Anxious people tend to stay too long, jump in too quickly and grip to the relationship,” Wilhide explains. “Secure people are comfortable with intimacy and autonomy. And disorganized people are highly reactive and deeply fearful of intimacy.”

There are numerous tests you can take to determine your attachment style, but healthy romantic relationships require individuals to identify and change harmful patterns that stem from them, sometimes with the help of therapy. You can learn to recognize when the impulse to stay or go is a “part of attachment and not the relationship,” Wilhide says, though that can still sometimes take a couple months to sort out. If you can’t be decisive after that point, it likely has nothing to do with the person you’re sharing a bed with, and more to do with insecure attachment.

“Most people end relationships because they don’t realize their heart is closed. When our hearts are closed, we will never connect with others — even if it’s something we want,” clinical psychologist Jennifer Rhodes warns, echoing Wilhide’s sentiments that “self-study and awareness is important when we want to connect with others.”

Therapist Elisabeth Goldberg agrees that if you have to keep asking if someone is right for you, you’re probably not ready for a relationship. “You have to know not what you’re looking for, but what you’re ready for in terms of a relationship. Feeling sick of dating doesn’t mean you’re ready for a relationship,” she says. “It means you either need therapy to find out why you’re attracted to the wrong people, or take a break altogether and focus on yourself.”

In the end, focusing on yourself may be a more productive pursuit for singles in quarantine, as opposed to using lockdown loneliness as an excuse to play house. Still, Shaklee is careful to note that self-improvement doesn’t have to be an excuse to shut out romantic possibilities completely, but just to be a little less thirsty about them. “It’s okay to slow down and just be friends at first. Why say goodbye to a good person, when you have a lot of compatibility factors in common?” she tells me, adding that this is especially true now.

“During a pandemic, relationships don’t have to be black or white. Each day or week, check in with your own physical, mental and emotional health,” she continues. “If a fellow single in your life feels good — and you’re both being safe — there’s a lot to be said for healthy companionship at this time, too.” 

As for me, until there’s a vaccine for my attachment style, I’ll just keep going to therapy. 

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