pile of cherries on table

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

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

Here’s his question:

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? Or, is your desired default to be actively looking for the right woman for you and then shifting into relationship once you’ve found her and gotten to know her?

Either way is great!

Just figure out 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 / etc. 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 partner 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, EMBODY that persona.

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

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 I coach 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.

Check out these free resources for introverted men to keep things going:

  1. Read her flirting signs.
  2. Convey interest in subtle ways.
  3. Find your uniquely attractive vibe.

Also, here is a huge 3,700-word post all about how to approach a woman as an introverted man.

If you are wanting more personalized support, check out our dating coaching program to see how we can help.