The Case for Dating Around: 6 Real Benefits of Casually Seeing Multiple People

Benefits Dating Multiple People at Once

My best friend has been single for the past six months, after being in a relationship for five years. I’ve watched her go through all of the phases I went through when I was freshly out of a long-term relationship: thinking about dating; dating; embarking on a dating freeze; swearing off dating forever, with and without a solemn oath; and trying on every state in between.

I’ve also noticed that she’s happiest when she’s dating a couple of people at once. This has changed now that she has started seeing someone she really likes, but until recently, I encouraged her to keep seeing this other, duddier guy throughout, just so she wouldn’t concentrate all of her anxieties on one dude. I advised her not to put all of her dating eggs in one basket, if you will.

I know how borderline insane that sounds, but I did that too when I was single: About six months after a long relationship ended, I dated two men, a professor and a crazy person, basically on two opposing sides of the spectrum, for about a month simultaneously. And it ruled. I knew I wasn’t serious about both, didn’t get hung up on either, and walked away bruise-free. Of course, once I met someone stellar, I stopped with the two-timing and focused my energy on one wonderful man.

As an aside, in this day and age, dating two (or more) people at once is not considered duplicitous or “two-timing.” Until you have The Exclusivity Talk, you’re free to gad about, dating whomever in whatever quantity you desire. This is the unwritten rule of dating in the modern age.

In light of all this, I asked psychologist Irene Levine, clinical professor of psychiatry at New York University Langone School of Medicine, to demystify the allure of dating multiple people simultaneously, once and for all. I asked her why distraction works so well, and why we are so much better at not freaking out about dating when we have a couple irons in the fire, even if neither of them is actually viable.

You have a built-in backup plan.

“When a woman dates more than one person at a time, she is less vulnerable because, should something go wrong with any one relationship, she can fall back on another,” says Levine. Women are planners, and those who think ahead enjoy backup plans. Just like we prefer to have an extra umbrella in the bottom of the closet and more than one pair of jeans, so too are we more able to relax when we have more than one dating partner.

You’re less likely to get hurt in a breakup.

First off, if things do end with one of them, one can “rationalize that the relationship really wasn’t that important to her, without a blow to her self-esteem,” notes Levine. Of course, this is impossible if feelings get tied up, heartstrings are plucked and all of that, but if you’re just casually dating, this is one serious benefit. “She hasn’t committed herself fully to one person, so she has invested less of herself,” Levine says of the woman who dates around. This results in less anxiety than when you go all in with someone.

It’s easier to just go with the flow.

Since you’re not relying on one person to fulfill all of your dating needs, Levine points out you’re more likely to be “satisfied” or at least “complacent with less than perfect individuals, each of whom provides something positive or worthwhile.” Plus, you won’t be wishing that anyone would be someone they’re not, because you’ll be more relaxed and “less likely to be demanding of any one relationship, even in terms of the other person’s fidelity,” she says. So if you have a date with Mark on Tuesday and Julia on Friday, and it comes out that they are also seeing others, NBD.

It forces you to stay honest.

It should be said that there is definitely such a thing as running around like a headless chicken, dating far too many people to ever feel any semblance of happiness. So how do you know if what you’re doing is constructive or calamitous? “It’s healthy to date multiple people if you aren’t ready for commitment and aren’t sure of what you are looking for, as long as you are honest with the people you are dating,” Levine says. In other words, if you’re ISO a diamond ring, dating three people at once is probably not wise. And if someone asks you point-blank if you’re dating anyone else and you say no, that’s just straight-up cheating. But as long as you’re still figuring things out and are truthful with everyone who asks, you should be good to go.

…And also stay in touch with your feelings.

Though this all sounds like a brilliant plan, there may be some drawbacks. “You may not be giving yourself the opportunity to truly get to know one person and may be avoiding intimacy,” says Levine. So go slow, and pay attention to how all of this makes you feel. You may be a one-woman or one-man kind of gal, and that is totally OK. Do you—and if you’re not sure what that looks like, experiment, but don’t go from 0 to 60. Try going on two dates with two different people in one week and see how that feels. Take it from there.

It makes any underlying issues bubble to the surface.

What if you’re only really serious about one person, but dating two just to distract yourself? I had to ask Levine about this, because I see it time and again in my friends, and though I’ve never been guilty of it—when I fall, I fall hard—it’s definitely a modern phenomenon.

If this is the case for you, Levine does not mince her words. “You probably need to assess whether there is really some red flag that is holding you back from having an exclusive relationship with that individual,” she says. If there’s no weird deal-breaker, perhaps “you are simply commitment-phobic,” she adds. If that’s your personal Achilles’ heel, it might be worth exploring why that is so.

In the meantime, have fun, be careful, and—I have to say it—be sure to exercise caution and use protection if you’re sleeping with more than one person.

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