Multiple Girlfriends: 9 rules to make multiple relationships work

This is a Bonus chapter from Kickassery. Not long ago, I got one of the best compliments of my life.  It was from a girl I had just started seeing.  When I asked her impression of me she said, “I think you are with a lot of women and you treat them all very well.”  It made me so happy because there is this cultural belief that if you see multiple women, you are a monster and a heartless player.  That doesn’t have to be the case.  You can see multiple girls and still be a good dude.

The structure I’ve covered up until here will lay the groundwork for you to make the same impression.  It’s honest, sexual, and unashamed.  It’s also about leaving everyone better than you found them.  It’s a potent cocktail.

Still, managing open relationships can be HARD.  You need to do things differently than ALL of your role models have before you (after all, how many people do you know in multiple healthy relationships?).  You’re exploring new territory.  So for this part you’re going to need to expand your mind and overcome some SERIOUS cultural programming.

Some history . . .

Any anthropologist worth his salt will tell you that Homo sapiens evolved in non-monogamous settings (though there is still debate over whether those were more harem-like Gorilla societies or free loving bonobo societies).  The rise of sexual exclusivity likely didn’t occur until the last 10,000 years with the rise of agriculture and private property.  10,000 years don’t mean shit to evolution.  Men and women alike, we’re biologically hardwired to seek multiple sexual partners concurrently.  You can place all the cultural software you want on top of it.  The instinct is still there.

Now I don’t tell you this so that you immediately break up with your girlfriend and live in accordance with “natural order.”  Nor do I tell you so that you can calmly explain it to your girlfriend and begin to comfortably date openly.  She’s liable to freak the fuck out.

I tell you this so you can say, “FUCK what I’ve been told is the natural order.  It’s a total load of shit anyway.  I’m going to do what feels right to me.”

Whether you prefer monogamy or non-traditional relationships doesn’t matter much to me.  But you need to realize that there is no divine fiat or immutable natural law that dictates one being better than the other.  It is not wrong to want to date and love multiple people at the same time, nor is it wrong to stay in a monogamous relationship.  Neither has objective justification.

Step one for a successful open relationship is to get that through your head and into your heart.  Read Sex at Dawn or The Ethical Slut for a full exploration of this topic.  For now, take it from me: 2013’s prejudice against open relationships is misguided.

Live however the hell you want.

Now for the steps to managing a multiple girlfriends!

1) Find your North Star

Get real here.

In a perfect world, what would your relationships with women look like?  Forget what your friends want.  Forget what society wants.  Forget what you think is possible.

You have no idea what is possible.

Decide what sort of relationship you would want if you were John Mayer and every girl in the world were begging for the chance to see you.

Do you want a girlfriend?  Do you want a bunch of one-night stands?  Do you want 3 girls you are seeing who love you as much as an exclusive girlfriend would, and the freedom to meet new girls as well?

Lock this in.  This is where you are going.  This is your North Star.  You need to be crystal fucking clear on this because if you choose open relationships, you will face some heavy emotional pushing to compromise on this point.  It is in those times that you will need to look to your North Star and follow it, despite the temptation to cave.

I decided that I wanted multiple girlfriends.  I wanted to love different things in different girls and I wanted the freedom to never stop exploring.  I decided that if you offered me the most perfect girl in the world on one hand, and the most perfect girl in the world plus the freedom to meet other great girls on the other, I’d take the other.

Know your goals and reassess often.  Don’t pursue a lifestyle you don’t want.  Don’t settle.

2) Be Honest

Rule #1 importance-wise.  Never lie.  Ever.  You are a piece of shit if you lie about this because you WILL devastate girls.

You’ve probably never gotten this real with people.  You’ve probably never told someone you care about them but refuse to date them exclusively.  If you’re caught off guard, you might revert to an easy lie.  So plan for the tough questions.

Seriously, proper planning is 50% of leading a moral life.  I’ll write more on this later, but for now take it from me: you need to plan for these questions.

Her:  Why won’t you date me?
Me:  I will date you.  I won’t date anyone exclusively though.

Her:  If you love me then why am I not enough?
Me:  Love does not mean being my entire world.  I love my best friend, but if he told me to drop all my other friends and go exclusive with him, it would be over.  There are too many wonderful, beautiful people for me to shut any doors.  And I am so happy that I maintained those open doors, because if I had been exclusive with some other girl, I wouldn’t have you in my life.

Her:  Did you hook up with someone else?
Me:  Before we ask this question of each other, we need to set some ground rules.  I am happy to talk about this and I want you to feel comfortable telling me about people you’ve been with if you want.  Personally, I won’t be asking, but you should feel free to tell me if it is important to you.  If you want to know who I have been with I will tell you things that don’t violate their privacy.  But regardless, you should know the answer has NO bearing on my feelings towards you.

These questions and more are all coming your way.  So know what the truth is and represent it wholly and thoughtfully.

My general philosophy: I do this because I know the world is full of amazing women.  I am 25 and I’d be cheating myself if I let any one of them, no matter how awesome, stop me from exploring the rest.  If I’m spending any amount of time with you it means I think you are an amazing person.  But exclusivity is not an option.

3) Manage expectations by controlling the cadence

Guys wind up in monogamous relationships they never intended to be in because things snowball out of control.

There is nothing wrong with monogamy, assuming that’s what you want.  But don’t close your eyes and let the relationship steer you.  Take control of where things are going.

If you are seeing a girl 3 times a week and speaking everyday, things are getting more serious.  Which is fine.  Just don’t wind up in that situation because you are humoring her.  Decide and manage the cadence of your relationship.

A few general guidelines:

Just hookups – Only contact her when you have something of importance to say or are planning to see her.  Plan on seeing her no more than once a week and usually only at night/the following morning.  Tell her you like that things are casual between the two of you and that you are happy there is no boyfriend/girlfriend expectation.

This can become friends with benefits or casual dating depending on when you see each other and what you do (dates, etc) but the management principle is the same: see each other no more than once a week to keep things where they are.  Compliment her on being cool and independent.  Tell her frequently that you want to remain single.

Open girlfriend – You have full license and encouragement to be as affectionate and loving as possible.

Be saccharine sweet.  You have my permission.

You can talk every day if you want.  You can say I love you.  But you need to be damn clear that things ARE NOT exclusive and they ARE NOT moving towards exclusivity.

A lot of girls think that after a period of time in an open relationship, you’ll come around.  That like “all guys,” you just want to have your cake and eat it too.

Explain that you aren’t looking to trade up.  Openness is a priority and a value in your life and it is not changing, even if you are swept off your feet.

Though you should be as loving as possible, what you need to manage are the rules you implicitly set up.  Habits create expectations.  

Think twice before establishing a:

  • Text cadence that demands a response every five minutes.
  • Every day goodnight call
  • “Drop in” policy at each other’s apartments
  • History of checking in with one another on night’s when you are out separately

These practices become common law for the relationship and can wind up causing issues if you are seeing someone else.

One last thing, for any non-closed relationship: Do NOT ever hide that you are seeing other people.  If you’re hiding something it means that you think it deserves to be hidden.  She’s taking her cues from you and you need to communicate with your whole essence that seeing other people is totally cool.

Closed – Society is pushing all relationships this way.  If this is what you want, you really shouldn’t have any issue.  If you ARE having issues there are 2 possible reasons:

  1. You lucked into the girl you are with (drunkenly?) and she now realizes you aren’t what she hoped.  You don’t have a problem getting a girlfriend.  You have a lifestyle problem.  Focus on Kickassery and you will become cool and non-needy.  Girlfriends will happen to you.
  2. You aren’t great at sex.  Good news.  There is a cure.  Read Sex God Method and thank me in the morning.

4) Consider the label

You probably don’t care whether you call it an “open relationship” or say that you are “single but seeing someone.”  I know I didn’t.  The label to me was secondary to the actual reality of our interaction.

Future Charlie to Past Charlie: Wrong idea bro.  I promise you: SHE CARES WHAT YOU CALL IT.  A lot.  If you introduce her as your “girlfriend” that shit gets noticed and it will be played back in her head for a week.  Again, nothing wrong with calling her your girlfriend.  But do not take labels lightly.  They can literally make or break a relationship.

Why?  Because if a girl is in a non-traditional relationship, she has to justify it to herself and her friends.  And they probably won’t like it.

It’s one thing for her not to keep tabs on that guy she is seeing, especially if you are both still “single.”  It’s totally another for her to have an “open relationship” and accept that her “boyfriend” is hooking up with other people.  Words matter.

Pro tip:  Don’t call it open.  Call it single.

5) Communicate the shit out of it

News flash: one conversation 2 months in about the status of your relationship does not represent a binding contract.  For most girls, you’ll need to keep your antennae up and allow the “What are we?” conversation to come up on a semi-regular basis.  It’s no fun.  Sorry.

It doesn’t matter how black and white you were about “never dating exclusively” in the beginning.  Part of her thinks that just might change.  So be aware and deal with feelings of confusion or jealousy OPENLY.

Read the Ethical Slut for more on this.  Candid communication is the bedrock of any successful long-term (open) relationship.

6) Win the friends

Her friends are your judge, jury and executioner.  Remember their names. Speak to them for 15 minutes each, alone.  Learn what they do and connect.  A girl can be crazy about you, but if her friends make her feel like shit for seeing you, you’re done.

If you get into a long-term relationship where you are “open boyfriend/girlfriend,” make it a point to show her friends what she means to you.  Commit random acts of thoughtfulness and loop them in.  Surprise her with a gift at her apartment.  Enlist her roommate’s help in making sure it arrives at the correct address and it set up correctly.  Thank her for her help.  Let her share in the happiness and thoughtfulness of the act and she will love you for it.

7) Keep her best interests in mind

Is she better off for having met you?  If the answer is no, you owe it to her to cut things off.

This means you need to seriously assess if she is emotionally handling the “openness” well.  Some girls struggle with it.  Some girls handle it super easily.  But after a few months, it is fairly common for her feelings to shift, so stay aware.

It may go without saying, but you should be willing to let her see other guys.  You’re probably going to have to work on your own jealousy, which is a whole ‘nother ball game.  The long and short of it is this:

Jealousy is just selfishness and low self-image.  It is the concern that she will do something or find someone that she likes more than you.  Shitty dudes deal with this by limiting their girl’s freedom.  You see it all the time in exclusive relationships.  Guy won’t let her go out, or if he does, won’t let her speak to anyone and freaks out if she does.  If she can’t do anything new, the dude’s position at the center of her universe won’t be threatened.

Know that you are awesome, independent of anyone she might like more.  Accept that she might find someone who suits her better.  Those things have NO BEARING on your value.  Don’t try to buoy your self-worth by placing it in her hands and then defending it from other suitors.  Keep your self-worth internal.  You are worthwhile not because any girl likes you, but because you are living a good life (you are living a good life, right?)

Lastly, take solace in this: if you’ve read and implemented Sex God, there is a 99% chance you’ll always be the best sex she has ever had.

I realize I’ve made a number of references to Sex God Method and that it is tough to find.  I’ll try to write a synopsis soon![/alert]

8) Get your values in sync

Some girls enter into open relationships hesitantly.  They have been conditioned to think poorly of them.  But they like you enough that they aren’t willing to not see you at all.  So they try it.

As time wears on, feelings of jealousy and insecurity will start to rival her attraction for you.  It will make her sad.  People are 100x more likely to avoid pain than pursue joy, so this can be a game breaker.  Ben and I have both been dumped for this reason.

If you want to go the long haul with a girl in an open relationship (1 year +) you need to get your values in sync.  She needs to agree that being open is good and worthwhile.  She needs to see jealousy as a challenge to be worked through, not a pain to flee from.

9) Realize you can’t win them all

Be awesome.  Get good in bed.  That will help.

But by only pursuing open relationships, you’re going to lose wonderful girls.

And you have to be willing to let them walk away.  It sucks.  It stings like a bitch.

Open relationships can be a recipe for instability.  They are about growing and stretching and pushing past content for extraordinary.  That means some uncomfortable and some unhappy along the way.

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