We’ve all heard the saying: don’t put all of your eggs in one basket. The reason for this, obviously, is that if you put all of your eggs in one basket and that basket comes crashing down, you’ve lost all of your eggs.

In this article, I’m gonna talk about the exact reasons why I don’t think any of us should be dating only one person and a time, nor expecting our partner to, and why dating multiple people at one time is actually a really good and, dare I say, logical idea.

I want to be clear that I’m not talking about being in a relationship with multiple people at a time, also known as polyamory. While that’s for every couple to decide, it’s not what I’m discussing here. What I’m discussing is the process of getting to know people, and specifically, through the lens of modernity. With that said, here’s reason number one.

Dating Is Like Job Hunting For Love

I’ve said many times that dating and business are essentially the same thing, just in different verticals. The only difference is that your dates are likely (…hopefully?) infinitely  cuter than your prospective boss, and that naturally the dynamic behind the relationship is going to be different.

The courtship part of the process, though – and the fact that it revolves around the cultivation and maintenance of a relationship – are identical.

Here’s an example:

You’re looking for a new job. You go on an interview. What do you do to prepare? If you’re smart, you probably put on your best suit, you check yourself in the mirror, make sure you look, smell, and come across nice. You try to present yourself in the best light as possible and put your best foot forward so the other person likes you for the job.

Now let’s examine the same situation framed for dating.

How do you prepare? Well, if you’re smart… you guessed it, you put on your best outfit, make sure you look, smell, and come across nice, and try to present yourself in the best possible light and put your best foot forward so you come across as the ideal candidate to date the person that’s in front of you.

The two, if you really break down the nuts and bolts of it, are the same.

Why? Because, as I mentioned, they’re both about the cultivation of, and as you move forward in the position the maintenance of, an interpersonal relationship.

When you’re in an interview situation, it goes without saying that you’re not the only one who’s applying for the job. There will be other candidates, and the interviewer will be sitting down with other potential prospects for the position, scrutinizing resumes and getting a feel for the person sitting across the desk from them.

But in terms of dating, some men have a hard time facing the fact that these women, although they aren’t even in a committed relationship yet, may go out on a date with them for the first time on Monday, and then with another gentleman on Thursday. This baffles me.

To be completely honest, I never date one person at a time. But the thing that startles people more than anything is how transparent I am about the fact that not only do I in fact date multiple people at once, but that I also don’t expect my date to only date one person at a time, either. I’ve even had some women push back and say, “But wait! I don’t want to date multiple guys at once!” What I came to find out is that, unfortunately, this is incredibly common.

Some would say there are biological and psychological reasons for this, such as that it’s hard wired into a woman’s mind since she can only get pregnant by one man at a time, and that this somehow ties into a man’s presence in her life, and so the expectation is for only one man to be present. But the thing is, we aren’t limited by what we’re supposedly “hard-wired” to do. Women have been smashing limiting beliefs about them for almost a century now, and show no sign of slowing down.

For clarification, when I say dating multiple people at once, I’m not talking about being in a committed relationship with multiple people at once; I’m talking about dating in the sense of spending time getting to know them, and going on dates in order to see if the person is someone you actually want to commit to or can vibe with.

So, without any further ado, let’s jump right in and cover the reasons.

1. Efficiency

By all means, buying a home is a financial business decision, and arguably one of the most important ones you will ever make.

If you were looking for a house to buy, would you call a realtor and say “I’d like you to show me ONE house, and only one house,” and based on that single presentation, make a decision to buy or not buy the home? Probably not, but let’s take it one step further. Would you only go to one realtor in the first place, rather than seeing what other realtors from other companies have to offer? If you’re smart, the answer is no.

Looking at multiple homes before you make a buying decision is the equivalent to dating multiple guys at once, or dating multiple girls at once. Using different realtors, in this scenario above, is the equivalent of using say, multiple dating apps to date multiple guys or multiple girls at once.

Let’s use another example. If you’re a really well-qualified candidate, do you only apply for one job from one company in the marketplace? Of course you don’t. Instead, you probably see what the market has to offer you, and make the best and wisest decision possible, based on your credentials, skill level, and what can be reasonably expected.

One of the primary reasons for this is that humans aren’t always honest. Many times people will try to lowball you and offer you things that are far below what your worth is in the marketplace. Now that’s all well and good, but how does this translate to dating?

I thought you’d never ask.

Dating only one person at a time is incredibly inefficient. What that really all boils down to, is that It’s going to take a good amount of time before you really get to know someone. The truth is that, no matter how much you think you know someone, you don’t really truly know someone for a good amount of time. There have been jokes before about this, where people say you don’t really meet the person you think you’re meeting right away… you’re meeting their representative. I’d say that’s pretty accurate.

At the end of the day it’s really about trust. And there’s only one way to build trust, and that’s with time.

Time and money are the most important resources we have, and of those, time is the more important of the two. Because while it’s true that going broke sucks, running out of time and dying is even worse. Meaning, once you’re broke, you can always go out and make more money. But once your time runs out, you can’t just zombify yourself and make more life. Time is definitely the more precious of the two.

The bottom line is that it’s going to take time to get to know someone, and by the time you actually know whether or not that person is good for you, if they happen to not be, you’ve wasted months of your life, figuring that out. And that’s never fun to do.

2. People Change

I touched on this in the last section about meeting people’s representative, but I wanted to expand on that a bit. As time goes on, people tend to get more and more comfortable around you. They may start by doing things that you really like about them, only to find out that’s not who they really are, that they were really only doing that to impress you. How many times have you been there personally, where a girl you dated gets super cute for you, then after a while, stops looking pretty for you and only ever sees you looking like she’s ready to hibernate in bed after a long work week?

This sucks, right? And how many times as a woman have you dated someone who took you out for a nice dinner or for drinks or dancing or an otherwise good time, to only pull the “Gotcha, Bitch!” act of not doing any of those things for you at all anymore?

People change. And when that happens, you get a chance to really get a glimpse at who they truly are. A lot of times, people like to date with the goal of manipulating people into thinking they’re the right person for the job, when in reality, they’re far from it. There are things about me that I know women hate. I’m messy. I have things laying around everywhere in my home and office. I have really bad A.D.D. I like spending lots of time on building my brands and companies. And yes, I always, ALWAYS, date more than one person at a time. I like personal space. But these are ALL things that I disclose right out of the gate, at the very beginning. Why? Because by doing this, I do two things that benefit her.

1. I give her the comfort of knowing she never has to worry about me being fake or changing who I am. I am who I am, whether she likes that or not, and I won’t change by chance, or by choice, or for anyone.

2. I give her the opportunity to decide if she wants to date someone like me or not, based on who I present to her as.

3. You Probably Won’t Get It Right On The First Try (or 10)

The other reason why I’m a huge advocate of dating multiple people at once uis because finding a wonderful, loving, attractive, and intellectually stimulating life partner is kind of like a woman finding a authentic Louis Vuitton bag at a thrift store – it’s not that it’s impossible; it’s just that it’s not likely without quite a bit of good effort.

Think of it this way – imagine that for each person you date, there are these little floating numbers that go from zero to one hundred above their heads that correspond to different attributes, such as intelligence, attractiveness, spirituality, and so on. If you multiply the number for each attribute by all of the many different attributes people can have, you can see how the combination of numbers not only makes each and every one of us entirely unique, but it gives you a road map for determining who fits into your life based on the things that are compatible with you.

Let’s say someone is very attractive and smart, but not spiritual, compassionate, or genuine. They’re “dog-eat-dog,” competitive, sneaky, and unfaithful. Just because you met a person who is incredibly smart and attractive doesn’t mean this person is going to be a good fit for you! Sure, it might take you a few dates to meet someone that attractive and smart again… but if you have to compromise on all of those deeper qualities, and if those qualities mean a lot to you, is it really worth it?

That’s for each of us to decide, really. But, in the long term, I’d wager to say it’s not, because someone like that presents a lot of liability. If you plan on having a future with this person, including marriage and children, then you’ve got to consider that if things do go south due to their volatile personality, now you’ve got children to think about, and the possibility that they might leave with half of your stuff. So sometimes, while it seems like a good idea in the short term, in the long term it really isn’t. Which is the basis for why scrutiny is key.

And dating multiple people at once is all about efficient scrutiny.

To put it another way, let’s imagine that you’re using one of the popular dating apps to meet people, like Bumble or Tinder. Can you imagine matching with only one person, and the very first person who swiped right on you, you decided was going to be the person you were going to date, regardless of how the date actually turned out? As crazy as that sounds, that’s exactly what dating only one person is like in the longer term, because they may be doing all of the right things today, but will they continue to do so in the weeks to come as they get to know you better and vice versa? This remains to be seen, which is why dating only one of the matches makes no sense.

At the end of the day, how you choose to meet people and what the relationship dynamic looks like is up to the two of you. But hopefully I’ve presented some pretty good reasons why in the beginning at least, you should never date just one person at a time. What are your thoughts? I’d love to hear your experiences.

Leave a Comment

Your email address will not be published. Required fields are marked *

Scroll to Top

Get My Latest Book on Gratitude