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

It can feel like an ethical dilemma: dating multiple women or one at a time? 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 each seeking clarity on how well you jive together.

Since that’s the case, the power dynamic is equal. This 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.

That said, be mindful of physical intimacy and large amounts of time spent together, as both of these dramatically deepen intimacy. So only proceed as you’re confident in where things are going. It is often wise to take your time and go slowly.

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 spending time getting to know whether this could be a fit.

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:


Preferred Lifestyle

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? 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? Are you ready to settle down, or are you just looking for casual dating right now?

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


Preferred Woman

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

What is she like? Is she loyal, kind, and 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 part ways sooner than later.

Whatever you do, don’t fall into the trap of sticking around just because you’re being passive. 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.


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 at the same time and you’re up front about that, then 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 filtering 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 going to settle for less than what I truly want, and I bet you’re not going to 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 can 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 feel good in your presence:


1. 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 these qualities are non-negotiables for you, and being false or fake is not an option.


It may be counter-intuitive after all the pickup artist advice you’ve read, but the truth is that your honesty and genuineness are the raw materials to attract wonderful women who are honest and genuine themselves.


2. Like attracts like.

Since a lot of women are on the same page about finding the right person for them through the process of dating, doing the three steps above will work well for you.

This is the case whether you’re meeting different women through social media, 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. Rather, you’ll have set up every interaction you have to be freeing and fulfilling for both of you.


3. 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’re also growing as a person. Enjoying someone is one of the most valuable gifts you can give to a woman. You can discover much more about this here.


Summary on Dating Multiple Women

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. It’s totally fine to be dating multiple people.

As long as you’re being open and honest with each of them, no pressure, you won’t have to question yourself, 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.”

This is our beloved ebook that 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 on page 8 of 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. Review how the program works, and if it seems like it could be helpful to you, apply at the bottom of the page to work with our dating and relationship experts.

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

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Attracting An Amazing Girlfriend Starts With Finding Your Own Vibe.

In this powerful free 22-page ebook, "Why PUA Doesn't Work for Introverts And What Works Instead," you will uncover...


--> A 3-step exercise to find what makes you uniquely attractive
--> Why the “pickup artist” approach will never work for introverts and what works instead

--> How to attract women naturally being your best self

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