Should you be dating multiple women or one at a time?

It can feel like an ethical dilemma:
one woman or many? Let’s explore.

The other day, I got a great reader question. I get variations of it often, so I figured it was worth answering here.

Here’s his question about dating multiple women:

“Should I be going on dates with the same girl until I decide I want her or not and then move to the next one? Or should I go on dates with a couple different girls and then decide which one I want?

“I’m torn because I don’t want women to think I’m a player, and I’d feel bad if I get a girl’s hopes up and then pick someone else instead.

“But at the same time I feel like if I date more girls, I’ll be able to pick someone who I really want and not just the first person who wants to be with me. The first person might be great though, so I don’t really know.”

Great question! My answer is three-fold:

It includes a quick, helpful mindset-shift, a shortcut to evade unnecessary awkwardness, and an integrity-check to make sure you’re giving off the right signals.

1. Quick, Helpful Mindset-Shift:

When you’re dating, you and she are BOTH seeking clarity on how well you jive together.

If that’s the case, the power dynamic is equal, which gives you both the freedom and self-respect to enjoy yourselves and make great choices.

The best mindset for dating is thinking of it as a playing ground for both of you to get a feel for each other in an honest, up-front, no-pressure way.

Neither of you owes the other anything but honesty.

If at any time, it’s not working out for either one of you, you are each free to move on. Keeping this top-of-mind is a liberating way to take the pressure off and enjoy yourselves.

2. Shortcut To Evading Unnecessary Awkwardness:

Know ahead of time what you want.

This results in minimal disruption to the women you date (and minimal awkwardness for yourself). Knowing what you want is two-fold:

First, know what you want in terms of dating lifestyle design. 

Is your desired “default mode” to be dating many women for the long-term, either casually or as part of an open relationship? Or, is your desired default to be actively looking for the right woman for you and then shifting into a long-term relationship once you’ve found her and gotten to know her?

Either way is great!

What’s important is to decide what you want, and be clear and unapologetic about it.

Second, know what kind of woman you’d like to be around.

What is she like? Is she compassionate, intelligent, fun-loving?

If you’re on a first or second date with a woman and you can see she doesn’t really share those qualities, then you can and should get out sooner than later.

Whatever you do, don’t fall into the trap of sticking around just because it’s free make-out/sex/company/et cetera. That’s because it’s important that you have integrity at all times.

Integrity is the only way you can ever respect yourself and sleep well at night.

It includes being vigilant about knowing what you bring to the table as a man and making sure that is met in the women you choose to date, especially any potential partner.

If you’re not searching for a serious relationship but are just wanting to play around and have fun, GO for it!

There is nothing wrong with that at all. It’s a fun thing to do and enriches everyone involved AS LONG AS you’re 100% honest.

3. Integrity-Check To Make Sure You’re Giving Off The Right Signals:

Being honest doesn’t merely mean being truthful with your words, though of course be that.

It also means being honest with your vibe. 

So if you’re looking to date multiple women and/or have one-night stands where both of you feel refreshed the next day, then EMBODY that persona.

Be that guy, and let the chips fall where they may.

Happily, you don’t have to chase anyone down. 

A woman who’s not into that won’t be into you from the start, and that’s wonderful! It’s liberating because you’re weeding out women who you’d otherwise confuse through careless mixed signals.

Most men we coach at Introverted Alpha want to date so they can gain experience and generate several options to choose a partner from.

For them, that’s the only way they can make a relationship choice that feels wonderful for them, instead of just “okay.”

If that’s the case for you too, then your vibe should be easygoing and open, as if to say…

“I am dating and seeing what’s what right now. Sure, if a woman knocks me off my feet, I’d be interested. Whether it’s Woman #1 or #100…

“The point is, I’m not the kind of man who settles for less than what he truly wants, and I’m sure you’re not that kind of woman either… 

“So, let’s get to know each other and see if this is something we want to take further. It may or may not be, and that’s alright. It’s at least worth visiting and checking out.”

From there, if you’re at the end of Date Three and she’s not yet brought it up, you should bring exclusivity into the conversation.

Other considerations…

There are a few other nuances to all of this, and all are good news if you’re a man of integrity who likes for everyone to enjoy themselves and feel good in your presence:

Honesty and genuineness.

If you’re resonating with this article, you’re likely not a big fan of pickup-flavored dating advice. It’s likely that genuineness and honesty are non-negotiables for you, and being false or fake is not an option.

If that’s the case, awesome! 

It may be counter-intuitive after all the pickup artist advice you’ve read, but the truth is that you have a head start that they don’t when it comes to enjoying dating multiple women.

Reason being, your honesty and genuineness are the raw materials to attract beautiful women who are honest and genuine themselves.

Like attracts like.

Since a lot of women are on the same page about dating multiple people, then doing the three steps outlined above will work well for you.

This is the case whether you’re meeting different women through online dating or in-person. 

From your first date onwards, and even before your first date in your text messages and your overall vibe, you can be up front with her about where you’re at.

As such, you won’t be keeping secrets or needlessly creating messy breakups or hurt feelings, even while casual dating. Rather, you’ll have set up every interaction you have with attractive women to feel freeing and fulfilling for both of you.

Presence and value.

When you’re with a woman, remember that you are two human beings feeling out a connection.

Whether it’s the first time you’ve met her, your first date, or quality time you’re spending together on date #14, be present to the one person in front of you. Give her the gift of your full attention and care in your free time together.

By doing that, you’ll be taking every date to the next level of fulfillment for each of you. 

You’ll also be growing as a person. That’s because rather than waiting for one day or next time to enjoy her, you’ll be enjoying her now, which is one of the most valuable gifts you can give to a woman.

Summary:

It’s refreshing to consider that you don’t have to play by the worn-out rules of a dating scene that makes you feel like you have to be somebody you’re not, a “bad boy”, or a player.

You don’t!

You can go on a date with one woman on a Sunday, another on Wednesday, and another on Friday.

As long as you’re being open and honest with each of them, no pressure, just transparency, then you won’t have to question your goodness and integrity, and neither will she.

Here are the three keys to dating multiple women with integrity: 

  1. Remember, neither of you owes the other anything but honesty.
  2. Know ahead of time what you want, in lifestyle and women.
  3. Be open and honest with your words and your vibe.

As you implement these steps in your own life, dating lots of women will go from feeling like a big deal to just being a normal part of real life for you.

Here are more resources to support you with dating: 

The best thing you can do right now is to download our free ebook, “Why PUA Doesn’t Work for Introverts & What Works Instead.” 

It walks you through developing your own distinctively attractive vibe, instead of copying anyone else, which isn’t as much fun and doesn’t work well anyway. Women want to know the real you, so it’s up to you to discover and showcase who that is!

Your next step to doing that is inside this ebook

And if you an introverted man who’s wanting more personalized support, check out our dating coaching program to see how we can help. If the program is currently closed, you can enter your email address on that same page to get notified the next time it opens.

Sarah Jones
Sarah Jones
Sarah Jones is founder and CEO of Introverted Alpha; the premier dating coaching company for introverted men; featured by Forbes, Business Insider, Cosmo, and more. Pick up your free copy of Sarah's 22-page ebook inside the blue box just below.

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