Should A Lady Date Multiple Gentlemen At The Same Time?

Photo by Michael Alan Hoy
Photo by Michael Alan Hoy

You know, I actually thought I knew how I felt on this subject — unabashedly PRO, as it seems wise to spread out the inevitable pressure (has he texted? has he texted now? how about now??) amongst a wide(r) swath of men. Or, like, at least two of ’em.

My thinking was this: Early courtship is such a fragile process that one too-quickly-returned text, one slightly desperate voicemail, one quasi-passive aggressive email can trash a perfectly graded slope toward, well, I suppose, a relationship. That is, if that’s the goal, which for me it (usually) is.

Although maybe the real goal is being offered the opportunity to decide whether I would like to pursue a relationship. (As opposed to it being decided for me — as in, decided against me. Sigh.)

Sometimes — when courtship is going particularly well — I have a tendency to become much too comfortable, much too fast. I’m sort of like the instant microwavable oatmeal of dating. I love flirting, intimacy and connection (love me! loveeee meeee!), and I fall in love fast, so I start saying things I should only say to boyfriends, or guys who have at least indicated through word or deed that, why, yes, they would very much enjoy seeing me sans clothing. For more than a single evening.

I have an exceptionally high threshold for flexting — no, not SEXTING, there were no photos — which means that sometimes I can flext a bit too hard. And maybe too much? I can see how it might be a bit aggressive to tell a guy with whom I went on two dates that I find him “incredibly sexy” (he didn’t text me back, for the record). Maybe I should save that for more captive audiences, like men stuck next to me on airplanes or handcuffed to my bed. Uh, for example.

But this leads into a more fundamental debate — the eternal, unending, somewhat nauseatingly unsolved debate — over whether one should attempt to follow “the rules.” The Rules, in my thinking, are just a tool to ensure two results:

  • That one plays into the cliche-but-damnit-they-work psycho-economics of the chase, supply and demand.
  • That one slowly unleashes one’s personality onto a willing (but still innocent) victim, like a time-release allergy medication, spread over the course of a period of weeks/months/years, such that they not freak out over any one incident/trait/facet until they have a better grip on your full context as a person — and thus ensure a slightly greater degree of accuracy when they attempt to assess whether that particular crazy incident is merely PMS or is, in fact, indicative of your crazy as a whole.

And that opens another can of debatable dating worms, namely, should you “be yourself”? Well, what the hell does “be yourself” even MEAN?? Which “self” specifically, should I be? Who I am with my girlfriends? Who I am with my mom? Who I am with my boss?? Who is the “real” self, anyway??

And what if myself has a ridiculously girly bedroom because myself loves pink, it just makes myself joyously happy, but I’m not sure I should show that to a guy on the first date. That said, maybe the guy who couldn’t handle that couldn’t handle me. Or MAYBE I need to give him a chance to get to know me so he doesn’t blow that (harmless! totally harmless!) pink bedroom completely out of proportion!

Photo by Michael Alan Hoy
Photo by Michael Alan Hoy

The point is this: the scariest part of a nascent relationship isn’t what he thinks of your bedroom (pink as it may be). It’s that looming cloud of rejection. What if I want him and he doesn’t want me??

And so sometimes I think, “Well, if I’m seeing more than one dude at a time, the likelihood that — at any given moment — I’ll get some positive response is fairly high, right??” Right?? And I have been right. And sometimes, dear God, I have been very, very not.

When I was in college, I wrote a dating column espousing a “newfangled” philosophy I’d discovered watching HBO (Thanks to Manolos-Clad Blonde Who Shall Not Be Named!). I called it “Dating with a Lowercase ‘d’” (oh, yeah, I came up with that gem). Apparently kids in college weren’t too familiar with the concept, so I broke it down its benefits:

“Dating with a Lowercase ‘d’: On the relationship spectrum, somewhere between hooking up and monogamous commitment (a.k.a. Dating with an uppercase ‘D’); usually entails traditional type “dates” as well as non-exclusive status … Casually dating multiple people is an excellent way to hedge your bets -– it broadens your dating portfolio. As long as both parties realize the relationship is not exclusive, there is nothing underhanded or immoral.”

So writes the 20-year-old me. I wasn’t wrong, per se. But I also neglected to realize — because I simply hadn’t experienced the phenomena — how unbelievably treacherous those “boundary waters” are. How two people — you and him — can physically experience the exact same things, and yet have a COMPLETELY AND UTTERLY DIFFERENT emotional experience. And how badly you can get hurt as a result.

Over the past five years, I’ve become the queen of the “3-6 monther.” Don’t be deceived by their length. They’re brutal. BRUTAL. You’re in that awkward but sort of ridiculously amazing stage where you’re not really sure what’s going to happen long term (could he be??? or is he just???) and you’re sort of falling for him but you’re not sure if he’s falling for you and you haven’t gotten comfortable yet, butterflies are still definitely involved, but then what if you want to date him exclusively and he doesn’t so shouldn’t you date other people to distract yourself and then what if he does and won’t that just be like stabbing you in the face with a hot curling iron??

And you don’t want to say, “Hey, I want you to be my boyfriend,” because you really really want to be one of those girls who is “cool” and just “doesn’t care” about commitment, because all the guys you know seem to be with girls like that, except you don’t actually know any of those girls. (WHO ARE THEY? WHERE DO THEY COME FROM?? And how much, specifically, Xanax is their ob-gyn subbing for their birth control??)

And what if you don’t even want him to be your boyfriend in the first place because maybe you’re not sure but then you think more about it and realize you’re not even sure that you’re not sure? Like what if you should just give him time? (Except you’re pretty sure he’s not “it” and then shouldn’t you just be dating other people? But doesn’t that mean you should just end it with him completely? But then you really should just give him time — and you’re back where you started.)

Basically, the 3-6 monthers drive you batshit crazy and then rip your heart out and none of your friends even sympathize when you grieve.

“It was only 5 months,” they say. “You weren’t exclusive,” they say.

Yeah. You know. That was the fucking problem.

There was a certain gentleman I dated for some time in 2008. (One of my BIEBNs, as I called them — “Boyfriend In Everything But Name.”) The fellow and I had dated for four months (four! months!!), we were seeing each other 3-4 nights a week, I followed ALL of the rules, planned a trip to meet my family in Chicago — and then, in a misguided effort to prompt the overdue DTR (Define The Relationship talk) I violated the number one rule of lawyers and potential girlfriends: “Thou Shalt Not Ask A Question To Which Thou Does Not Already Know The Answer.”

“Um, so, don’t you CARE if I sleep with other men?”


“Nope,” came his unperturbed answer. And in one word, there went our relationship.

I still remember that feeling, like all of the air went out of the room. I looked into his face, the face of the man I had spent the last four months courting and being courted by, into the face of a man I had grown to care about very much, and I couldn’t understand his words. He didn’t care. HE DIDN’T CARE??? How could he not care??

The relationship — having never been made exclusive — didn’t actually die right there, but its soul did. The physical manifestation continued on life support for a month or two longer. I started going on dates with other people to distract me, to ease the pressure on what I wanted. (A relationship! With him!)

And then, there we were, together at a holiday party. We didn’t come together — but I certainly thought we were leaving together. In the corner, me in a red dress and green sparkly heels, him in a cashmere sweater with a tie — he told me he was leaving with someone else. Which, technically, he had every right to do. We were dating multiple people.

One too many holiday cocktails to the wind, I punched him in his cashmere stomach and ran outside, sobbing. It was December in New York, just bone-chilling, and I didn’t even feel it as I cried in a taxi, Taylor Swift style, all the way home.

Julia Allison's green sparkle shoes!
Julia Allison’s green sparkle shoes!

Dating multiple people didn’t change this one wretched thing: the only person I really wanted to be dating was him.

So perhaps the lesson — if there is a lesson, if there is EVER a lesson in this exhausting dating dance — is that, oh, hell. I have no fucking clue.

Arranged marriage anyone? Thought Catalog Logo Mark

This article originally appeared on xoJane.

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