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How To Succeed Dating Multiple Women in 2024 (It's Not Easy)

He's dating multiple women and texting one of them

Before you start dating multiple women, you may want to read this article before doing anything risky. Dating more than one woman at a time is fraught with dangers and controversy, and the only way to stay safe (and sane) is to be 100% prepared.

First off: In case you’re feeling bad about the urge to date multiple women, don’t be. As human beings, we’re all driven primarily by the hardwiring that Mother Nature has left in our brains. And while women are driven to find the best possible man for themselves (even trading up to get him), we men are primed to spread our seed.

Hence the desire to meet, date, and have sex with different women.

Of course, this urge can lead to disastrous results if left unchecked. That’s why the key is to keep it checked with knowledge and discipline. And the first step is to know what to expect when you start dating more than one woman at a time.

Why Do Guys Want Multiple Girlfriends?

Again, by default, we’re slaves to Mother Nature’s designs. Like most biological beings, our primary drives are to feed and procreate. That’s why most healthy men will always feel the urge to meet, flirt with, and sleep with new women.

Now, of course, it’s difficult to square that natural urge with its social ramifications. If monogamy hadn’t become the standard for society, each man would be forever locked in a battle against other men for women. Society would stagnate, populated by sex wars and abandoned children.

So how do you date multiple women and still be a productive, accepted member of society?

Here’s the answer. Most men (and society in general) don’t distinguish between girlfriends and lovers. And I believe it’s this distinction that holds the best solution to the conundrum.

The difference between “girlfriend” and “lover”

Is she a girlfriend or a lover?

A girlfriend is a step in the traditional courtship system. It’s one step behind “fiancée,” and two steps behind “wife.” It’s a temporary status for a woman that her man is supposed to “upgrade” for her at some point in the future.

Simply put, a girlfriend is a wife-in-training. She and her boyfriend are meant to love each other exclusively, preparing themselves for the rigors and responsibilities of married life.

That makes sense, right?

Meanwhile, a “lover” is different in the sense that there’s nothing romantic between you and her. Your relationship may be fun, sexual, and thrilling—but there are no promises of “upgrading” on the way to marriage. Essentially, it’s being a part of hookup culture where there’s no commitment. And both parties agree to this setup before making things official.

Unless you subscribe to a polygamic or polyamorous lifestyle, having multiple girlfriends is as unsustainable as it is controversial, as you’ll soon see.

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The pros and cons of having multiple girlfriends

When you have multiple girlfriends, you’ll get the love, affection and support of more than one woman. The problem? Unless you’re living an openly polyamorous lifestyle, your girlfriends ideally won’t know about the other women in your lives. Ever.

That’s probably the only “pro” I can think of. Meanwhile, the “cons” of having multiple girlfriends are many:

  • The exclusive demands of all your girlfriends can be too much for you to handle.
  • If you don’t keep all your girlfriends happy, word will ultimately get out of your philandering ways, complicating your relationships further.
  • People finding out about your multiple relationships won’t just hurt your reputation—it can also hurt your career. If word of your misbehavior reaches your workplace, you can lose your job.

So yes—if I were asked, the risks and potential downsides of having multiple girlfriends far outweigh its benefits.

That’s why I heartily suggest the alternative...

The pros and cons of having multiple lovers

Hooking up with one of his lovers

The disadvantage of having multiple lovers and no girlfriends is that there’s no real love going on. Your dates with your lovers are fun, hot, and sex-driven—but that’s as good as it gets. If you and your ladies all live up to the agreement, none of them will ever become your girlfriend, fiancée, or wife.

Meanwhile, the advantages are many. If you can find like-minded women who gladly agree with your rules, then you can enjoy the following perks:

  • You have choices—if two of your lovers are unavailable for the weekend, you still have a shot with the third, for instance.
  • It’s much more sustainable since you won’t be paying for their rent, gas, spending money, etc. All you need to spend on are your dates.
  • Since expectations are lower, there’s no jealousy. Your lovers are free to see other men and not tell you if they wish.
  • If the word did get out that you were sleeping around, it wouldn’t hurt your reputation or career. After all, you’re technically a single, unmarried guy.
  • If any of your lovers want to end the relationship, it’s not a big deal. No messy breakups or divorces are to be expected.

And by the way: This isn’t new. In some circles, this is called “rotational dating,” and both men and women do it.

Needless to say, if you want to date multiple women, I highly recommend taking the “lovers” route. It’s simpler and easier, and the risks are much lower. If you agree, then heed my advice before you go out and start looking for potential lovers.

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Tips on Dating Multiple Women

I can't say it enough: Your success will depend on your discipline. I suggest you stick to these rules like glue:

Set their expectations

First of all, set the right expectations with each woman whom you want to be your lover. Make it clear that you’re not interested in commitment, and just want a casual, laid-back, fun relationship—not unlike a friends-with-benefits setup.

Here’s a good system to follow:

  • Meet new women regularly. Be fun and flirty. Be a good conversationalist.
  • Eventually, some women will like you enough to flirt back. They’ll do this by talking about sex and relationships, mentioning they’ve been single for a while, or hinting they want to be more than just friends.
  • You can then mention your availability by telling her something like: “I think it’s no one’s business who people hook up with. For instance, if you and I were to hook up, we just need to agree to three things: One, no kissing and telling; Two, no falling in love; And three, no feeling guilty. If either of us can’t agree to those three rules, then we’re better off just being friends. Makes sense, right?”
  • Take note of the friends with benefits rules all guys should follow.

If she’s still interested, she’ll keep flirting with you. If she says something like, “I like those rules,” then congratulations—you’ve found your next lover. Now, you might want to make it official by scheduling your next date—preferably sometime soon, and somewhere close to your place (or somewhere private you can take her).

Of course, your mileage may vary, so feel free to experiment and find a system that gets you the results you want.

Stick to three lovers tops

Three women he's hooking up with

You can flirt with as many women as you want but have only three lovers tops. If you meet each of them once a week, it’ll take enough of your time, money, energy as you can handle.

If you feel you have the resources to handle more, go ahead. If you’d like to stick with two lovers instead of three, that’s fine too. The important thing is to make sure your system works for you, and not the other way around.

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Don't chase; replace

Lastly, know that none of your lovers will be around forever. In most cases your relationships with your lovers will last between 2 to 9 months—but they will end.

How do lover relationships end? Here are the most common ways:

  • You decide to upgrade your favorite lover into your girlfriend, so you need to stop seeing the others.
  • She wants to upgrade to girlfriend status, but you’re not interested in commitment, so you part ways with her.
  • One of you gets bored of the relationship, so you agree to stop seeing each other.

My last tip is this: Once you let go of a lover, be ready to replace her. If you try to get her back, that’s a sign you’ve gotten attached to her, which means you broke your own rule on not falling in love. Chasing her will only complicate things and expose you as a wishy-washy guy.

So again—don’t chase. Instead, replace her.

If you meet enough women regularly, then you should have a few potential lovers waiting in the wings. Go meet them, run them by your system, and see which ones will be more than happy to be your new lover.

I hope you see the logic by now. If you do decide to date multiple women, it’s best to keep them at the “lover” level. It’s more sustainable, it’s more fun, and you’ll be making each other happy for months to come.


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