Why You Should Always, Always Date 3 Guys At Once

Oprah says when you find a pair of shoes you like, buy “A pair and a spare.” I tell my girlfriends to apply that method to the men whom they meet.
Publish date:
January 15, 2013
Dating, men

“Peter is so interesting, and brilliant, but his penis is kind of small,” my friend Melissa lamented to me over coffee. “And I like Frank a lot. Our sex life is great. His penis is just the right size. But he’s…kind of boring.”

And therein lies the rub. There’s no way to find the perfect man. Hint: He doesn't exist. So, many of my single friends are out there looking, and looking, and looking, hoping they might find that special numero uno. When they are disappointed, they turn to me.

Why? I think it’s because I’ve been in many serious long-term relationships, which sounds kinda bad to say it out loud. I’ve been engaged at least 2 or 3 times, and I have 2-and-a-half diamond rings to prove it. I’m definitely good at keeping a guy around for years at a time, which is not necessarily anything to brag about.

My secret? Patience meets a high sex drive? Perhaps. A saint-like tolerance for dumb dude shit? Yes. Self-esteem challenges combined with abandonment issues? Ding. Ding. A-ling.

For some reason, my friends think these faults mean that I have some wisdom to impart regarding dating, even though I have made more mistakes in courtship than I care to admit, including dedicating myself to a narcissistic sociopath for several years (I was too young to know better), cold-heartedly dumping a very kind and sincere man who treated me like gold (he bored me), and refusing to go on a date with Russell Brand (I didn’t want to be just another one of his sexual play things).

And those are just a few of my big strikes.

Currently, I'm engaged to a very nice man I met on the internet. I put a Craigslist ad up that outlined all the exact and specific things I was looking for in a man (Passport, college degree, good relationship with mother and more) and I received 300 responses. Sure, 50 of them were dick pics, but this is New York.

I went on several dates and settled on a very nice hipster-ish man who was tall, creative, smart, a hard worker, 8 years younger than me, handsome with great hair, eyes and teeth (three of my demands) who made it clear to me that he was not going to screw around with me on an emotional level.

I spent years dating men who were very hard to manage and decided that I'm too tired to chase men around anymore. I kind of put it in my mind that whoever the next man was who I found and fell in love with would be the man I'd marry, if he proposed, and he did. Things aren't perfect, but they never ever were and I don't believe it's possible that they can be. However, it's as close as I've ever found to perfection.

It's a safe, warm, comfortable place and I'm happy to be here. However, if I were still out there looking, knowing what I know now, I'd go about the dating scene a little differently.

My phone rings. It’s Hanna. She says, “Will I ever find a guy who I’ll like enough to want to marry?” I exhale and answer honestly. “I don’t know how your brain works,” I say. “But the chances that you will find one person who has all those perfect qualities that you want are very low. You can, however, find those characteristics in several different men…”

In a relationship, the one who has the most power is the one who is less emotionally driven, i.e., the one who loves less. If two people are “crazy about each other,” that can create a really sick dynamic. That may not always be the outcome, but I have not yet seen a relationship (including my own) where two people were “crazy about each other” that was not co-dependent, or at least not riddled with problems.

There are many reasons why two people would stay together for a long time. Both have decided that they perhaps want to have a family, and that the other would be a good person with which to make a family for a collection of varying factors. Or perhaps one has enough money to take care of the other for a lifetime. As my Grandmother always said, “It’s as easy to fall in love with a rich person as it is a poor person.” So true!

So let’s get down to it. Looking for that very special one? I strongly recommend the pair and a spare method. Oprah says when you find a pair of shoes you like, buy “A pair and a spare.” I tell my girlfriends to apply that method to the men whom they meet.

I suggest women seeking a husband or a long-term companion, or even just the best men they can find for fun and memories choose a couple good guys, and then toss a third one in to complete the trifecta. Dating more than 3 men at a time gets too difficult to keep track of. It’s really too much. 3 is the perfect number.

Two is too few. When you meet a new man who you like better, rotate him in, to take the place of the one you like the least. As you get more familiar with the three, the best one will become increasingly apparent and you can eventually tune the men out who you like less.

I’m not suggesting you have sex with them all, unless you want to, but if you take your time and get to know many men, all the while keeping a few good fellas around to keep you company, you will never be lonely, you will never be desperate and your self esteem, if low, will level out. How can it not when you have so many men vying for your attention?

When you date one man, you crave him. You want to know where he is, what he’s up to, who he’s with, if he’s thinking of you. If you date two men, you still have enough free time to wonder these things. But if you date three, when you get time to yourself, you’re happy to be alone. You’re glad to relax on your own or spend time with friends. You’re certainly not wondering what any one is up to.

Men do this all the time. Many of the men you know have several relationships going on simultaneously, whether they tell you or not. Some who do might even surprise you. One friend of mine, an unassuming dot com business owner juggles girls like he's in Cirque du Soleil. He looks like a nerdy nice guy, yet, he's taking a different girl out every few nights.

“I’d never promise monogamy to a man without him offering it to me first,” my friend Denise told me, once. “And it’s never yet happened, in all my 20 years of dating.”

So the next time you’re wondering why some guy isn’t calling you that you wish was calling you, instead, go meet a couple more guys and add them to the pile, always keeping it at three, unless / until you find that favorite one.

But as my friend suggested above, don't give away your gift of monogamy. Let him be the one to ask. It will make him cherish you, and that's the truth. And keep and spend time with your male friends, and insist he spend time with his friends. It's imperative to have time apart, and often. Even if a man asks you to meet with him night after night, you must say no. If you have other boyfriends, this is easy to do.

I know I'm going to get some serious flack (I said it, FLACK) for writing this article. I'll hear arguments from all sides and I expect some people to disagree. I understand that not all men are identical, and not all women want or need the same things. This article isn’t a blanket statement about how to date.

It’s only for women who want to get control of their emotions in dating and find the best men -- and possibly, ultimately, the man (singular) -- they can. It's for women who are tired of having guys tie their heart strings up into knots. I can relate, as a woman who was out of control of her emotions with men for years.

The pair and a spare concept is a simple dating truth. The more men you have, the more you understand how little you even need any men at all.