Start a Dating Bracket and Juggle Several Men At Once

Would happen if women organized their dating the way men organize their fantasy football tournaments? Hear me out…

Elisabeth Ovesen | NYT Bestselling Author
Published in
8 min readJan 21, 2022


GIF: Notice Daphne's dance card, popular in the Regency Era. (Bridgerton, Netflix)

These days, if a woman went on a date with one man on Monday, another on Tuesday, and a different man every other day of the week, judgmental onlookers might call her loose, a tramp, whore, or slut. These days, and for many decades before this one, women are often shamed for exploring their romantic and sexual options. After all, if a woman investigates what life has to offer and learns what and who is best for her, she's less likely to settle for situations and relationships that don't meet her standards. This means that more people, more men, will be met with rolled eyes and no thank you's. For a large percentage of egotistically fragile dudes, including incels, this sort of rejection is unbearable. So, they shame women, hoping women will put all their proverbial and actual eggs in one bullshit basket and settle for whatever and whoever chooses them.

GIF: Bridgerton (Netflix)

Although dating just one man and settling for him when he finally chooses you may seem like the most old-fashioned way to be, a quick dive into courting rituals of the past show that even in the most conservative of eras, women were expected to be courted by many men at once. In some societies, like the type seen in Netflix’s beloved series, Bridgerton, if a woman was seen with a man more than twice, it was assumed they were engaged or about to be. At social events like dances and balls, a woman's dance card was expected to be filled with the names of many different men. Single men and women were expected to mingle and socialize as much as possible until finding their perfect match.

In those societies, if a woman had no suitors, she was less desirable to other men. If she had only one suitor and saw him too often, he'd better marry her. For a woman, the goal was to have many men vying for her affections until one broke away from the pack to win her heart and possibly her dowry. So, in considering these specific practices and the use of dance cards, which date as far back as the early 1800s in the United States, dating many men at once is actually very old-fashioned!

That said, what would happen if women raged against the patriarchal and puritanical constraints that apply only to them and not men? What would happen if they took up the practice of keeping their dance cards full while on the lookout for the right partner? And what would happen if women organized their dating strategies and partner selections the way men organize their fantasy football tournaments? Hear me out…

GIF: Bridgerton (Netflix)

I call it a Dick Bracket. You can call it a Dating Bracket if you’re not as cheeky as I am. I started this practice as an experiment in my late twenties while doing research for my second book, The Vixen Manual. Looking back, I wish I kept it up far longer than I had, instead of allowing myself to feel pressured into getting married in order to be respected in polite society.

Because, really, fuck polite society.

My Dick Bracket was fun to run and taught me a lot about myself and the men I dated. It was my version of a dance card, and the men on it were encouraged to go above and beyond their usual wooing procedures if they wanted to spend time with me. Instead of letting men dictate how the relationship unfolded, giving each of them equal time and access, and chasing them, I reserved my efforts and let the men do all the courting.

It was refreshing.

It was lovely to allow men to make fools of themselves, to show themselves as they were instead of imagining them as I wished they were. It was nice to stop trying so hard to make a man like me, and instead, allow him to try and convince me he was even worth my time. It was balancing, as a sexually autonomous feminist, to update a page from old-fashioned courting etiquette, apply it to modern times, and let new fangled men struggle with the notion of not having pussy thrown at them just because they were young, handsome, and successful. And I have to admit, it was deeply satisfying to watch them squirm as they moved up, down, and off my list. Here's how it worked:

GIF: Bridgerton (Netflix)

I populated my bracket. It all began with a Starting Five, each of them coming in at number five. These were the men I was interested in the most. Eventually, each would either end up in the Friend Zone, the Suitor's Circle, or the number one spot — Lover's Lane. I wrote their names in a notebook and left space to rank them.

I ranked accordingly. Over the next week, I paid close attention to how they behaved. I looked for traits I liked and those that turned me off. I made a note of how attentive, respectful, and caring they were with me, and even how they treated others. For each good deed or trait, I gave them a gold star in my notebook. Then, at the end of the week, I moved each man up, down, or off my bracket according to how well or poorly he did. I repeated this step weekly.

I set boundaries. Each man was given a specific set of rules to follow according to his rank. For instance, a low-ranking suitor (a Four or Five) would be forbidden from contacting me after 6:00 p.m., just in case I was invited out by a higher-ranking fellow. Number Four and Five were also not allowed to see me in person. If they wanted a face-to-face date, they had to find creative and thoughtful ways to entice me. Number Three had his own set of rules, as did Number Two, and the man who occupied the Number One spot in my life had fewer rules than anyone, and only he got to be my lover. That lucky bastard stayed my lover for eight years.

I benched the extras. I always kept a couple of guys on the bench for when one of my low-ranking suitors fell out of the bracket completely. These were likely men I met while out and about but hadn't given a chance to woo me. Naturally, anyone I took from the bench came into the bracket as a Five and was given a chance to work his way up. Although, honestly, few men ever did. At that time in my life, there was only one Number One and no one dethroned him.

I told them where they stood. What surprised me about this little experiment, is that when some of the men in my Dick Bracket asked why they weren't allowed to see or call me, and I explained my process, they thrived on the competition! So, I decided it was best to be honest with all my suitors and prospects about my experiment. After that, they would call and ask where they placed that week, who was ahead of them, how they might have fallen in the ranking, and how they could do better.

I'm not saying you should start a Dick Bracket. I'm also not saying you shouldn't because it was a lot of fun and something I intend to try again while working on my next book. What I am saying, however, is that if you're single and interested in dating, it might behoove you to date several people at once. Time is a-ticking. Settling for the first man that comes along may seem to save time, at first, but spending years with the wrong man is the best time waster of all. You’ve got to be sure. You have to explore and then weigh your options, and never ever settle for less than you’re worth. The truth is, although some women have been lucky enough to find their matches early in life and go on to live happily ever after, most of us have been kissing frogs since junior high.

We’ve been staying too long in relationships that were never right for us, desperate to make something work. We’ve been looking at our biological clocks as the years dwindle, wondering how long we have until our wombs turn into pumpkins. We’ve been racing against time, focused on creating a storybook ending instead of slowing down, enjoying our experiences, learning from them, and quickly moving on when red flags appear. And then, a decade into a dead-end relationship, it ends. All of our eggs are tossed from our baskets, and many of us are left wondering how we’ll ever get the courage to start all over again.

It doesn't have to be this way.

Take your time. Explore. Compound your options and put them to the test. Don’t feel grateful when a man chooses you. Be empowered to do the choosing, too. Reject, rearrange, and restart. You never have to settle. You never have to stay. If you choose to date multiple men at once, whether or not you form a bracket, don't allow others to shame you for it. There is nothing “slutty” about exploring your options, but even if there were, who the fuck cares. If there’s one thing we’ve all been reminded of in recent years, life is too fickle and short to live by other people's rules. Make your own, or make none at all. However and whoever you choose to date is your business, so long as you are transparent with those involved.

And, indeed, there are countless old-timey traditions and social norms we should definitely not borrow and bring into what is supposed to be a more progressive time in history. But, there is something to be said for the regressive ideas society still has about sex, sexuality, and dating, especially where women are concerned. So, if we can borrow evolved bits and pieces from a time gone by and implement them in new and inventive ways, why not? Why not take the idea that women should be chaste and at the mercy of men's choosing and turn it on its historical ear? Why not fill our proverbial dance cards, decide who receives our attention, how much of it, and when? And most notably, why not deny underserved men a level of interpersonal access that far surpasses their level of effort? In other words, make them work for it, girls!



Elisabeth Ovesen | NYT Bestselling Author
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3x New York Times bestselling author, art enthusiast, and design girlie living between Los Angeles and New York City