Multiple Girlfriends: 9 rules to make multiple relationships work

This is a Bonus chapter from The Anti-Pickup Line.

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, “SCREW what I’ve been told is the natural order.  It’s a total load of crap 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: 2014’s prejudice against open relationships is misguided.

Live however the hell you want.

Now for the steps to managing dating 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  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.  Check out The Anti-Pickup Line 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  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 heck 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 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 the freedom of the girls the date.  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.

9 Comments

  • Taylor 23 weeks ago Reply

    Awesome article. I live this way these days and its nice to see someone make such a good non psychobabble synopsis of it.

    I usually hit them with it on the first date. I ask them what they are looking for in a guy, which leads them to ask me the same question, and i lead that to that i am not looking for a girlfriend in the traditional sense of the term, that i want to keep things casual and not too serious, and that im not into hookups or one night stands, that i want to see someone regularly for dates and activities as well as maybe more between the sheets.

    Ive only had one flat out reject it. The rest landed in my bed in a couple of dates if not on the first. The one who rejected it kept rattling about monogamy she said the word so many times it made me cringe after a while. She freaked out when i made comment that another girl was pretty, or an ex girlfriend was hot. When she pressed me on the monogamy thing saying no sex until monogamy, id had enough.

    I told her wed only been on two dates and id never give up seeing other girls just to see what sex was like with one id never had it with. She retorted that we talked on the phone for hours but i came back with that weve never had sex, so her version of “monogamy” she was demanding was in fact celibacy. That i was to stop dating other girls for the first prerequisite to have a *chance* at sleeping with her was lunacy. She didnt get it. Havent talked to her since.

    I contrast this above story with anoher girl i met while multi dating. She was multi dating herself and i adore her, id actually marry the girl and go monogamous with her if given the chance. I knew she was going on other dates and sometimes she would cut a date short and come over to my house afterward because she wasnt into the guy. She ended up moving out of the city and into a boyfriends house as part of the move but still occasionally come over and have sex with me. I knew what was going on but the boyfriend likely didnt – she is on pills and he is using rubbers and im not with her, he doesnt know shes on the pills. The point im illustrating here is that i know full well she is living with and presumably sleeping with her cohabiting boyfriend, that she may even be seeing guys other than him or me, and i dont care at all. I find her adorable and still love her to bits – without a hint of jealousy. That she talks to me every day and comes over for mad sex in the afternoon and makes me feel like a god, thats what i love about her. I could care less about someother dude.

    In contrasting these two examples it reinforces your article.

    The woman who demanded monogamy as a prerequisite to sex obviously had some self esteem issues because she couldnt bear me even making comment that a previous and now ex girlfrie d was very attractive (hence why i put up with her crazy) . There was zero foundation for any kind of a relationship as id barely known her a week and met her once plus about 15 hours on the phone. To drop the other 6 girls i was talking to for a chance with her would be ludicrous. She was maybe a 4/5.

    The girl who was dating other people and has a boyfriend, ive been seeing for six months now and were still going strong (albeit the boyfriend thing is a pain in the neck at times). With events unfolding as theyare, i will spare personal details, i wouldnt doubt that she ends up breaking up with her boyfriend, seeing me more often, and looking at moving back into town and maybe going exclusive with me within a few months. She sees that i love her the same when she lives two blocks away while dating other guys as i do when shes sleeping with another guy almost every night because she lives with him and hes her boyfriend. Thats love.

    Great article again

  • Kate 19 weeks ago Reply

    Is there a way to figure out what you want before trial and error? I have a friend with benefits and I don’t care if he sees other people, but he didn’t call me for a couple weeks bc he was busy which I don’t mind except he never said in busy I’ll call you in a couple weeks he just kept not picking up or saying he was busy which made me angry. I feel like I wasn’t supposed to get angry at this because it’s a fwb relationship, so instead I just went back on okcupid and went on a couple dates. When we hung out again I was just less into him because I kinda emotionally detached. I told him I was annoyed he hadn’t called and was worried he felt incompatible and he didn’t have a clue he was hard to reach. So… How do you navigate these situations? I feel like I want to date casually because I’m exploring and focused on my career but I also want someone who a) wants to hang out b) wants to have great sex c) calls/texts at least once a week. I don’t have to hang every week but just some contact that they initiate. So advice/help?

    Also, while I’m asking you questions, does having sex with a guy make them like you less if you have it on the second date because it’s not enough of a challenge even if you both really want it?

    • Charlie 18 weeks ago Reply

      So you can have whatever rules you want. The important thing is just to make them clear.

      In this situation, you didn’t do that. You left it unspoken. He thought it was okay to not contact you. That pissed you off.

      Instead, just calmly discuss this sort of thing early in the relationship. Like right after having sex for the first time at the latest. If you do it from a non-needy place, it won’t come off as creepy stalker. You can just relaxed, say something like, “So that was fun. I have no idea where this is going, but I know I’m not interested in a serious monogamous relationship.

      If they are “hard to reach” still bring things up. If you get a stonewall, just be like “So I’m not mad, but I just want you to know, that I need more open communication in whatever we become. So seriously no hard feelings, but I don’t want to continue seeing you if we can’t openly discuss what we are.”

      The key is to remain calm and truly have the attitude that if they don’t want to behave by a certain set of ground rules (ie communicating clearly about the relationship) that it’s better off ending, no hard feelings.

      To your second question, I can’t speak for all men. I can say that sex is important to ME and I think the idea of being a “challenge” is horribly backwards and misogynistic. If a girl and I like one another and there is chemistry, we should hook up as soon as we have privacy. That freedom would make me like her more. After all, why would I think less of someone for sleeping with me?

  • Thomas 19 weeks ago Reply

    All nice and well. But what I’m searching for is a harem. I find all this ‘equal open search stuff’ understandable. But I want a true harem with girls who would only be allowed to adore me, how would i achieve this? You’re talking about your instincts free of cultural programming; my deepest instinct says: I want a bunch of girls whom I can date with whenever it pleases me, but they can’t date other guys. How will I achieve this? I think this is thé true challenge a lot of us guys face. Because letting that wonderfull girl leave if she doesn’t concur with your open relationship deal isn’t an option. And please don’t ignore or do away with this comment saying i’m unfair, selfish or a monster. What i describe is a true dream for many guys but they can’t even bear to think about achieving it because it seems so utterly impossible and thus pointless. I’m very curious about your response.

    • Charlie 18 weeks ago Reply

      As long as two adults are in a consenting relationship, they can do whatever they want. So I’m not here to pass judgment on what you want.

      What you’ve said though traps you. You want something that not many women are going to go for. Yet you don’t want to let women you like walk away. The tough news is that you have to either let people who don’t want what you do walk away or you have to change the relationship so it fits what they want. You can’t just take any person and convince them to join an untraditional relationship. At some level they have to be open to it.

      Best bet: look for women who would be open to what you want. Bi sexual women come to mind. Be honest and open about what you want early. Screen out those who aren’t interested. You are going to miss out on a lot of women who don’t want the that kind of relationship, but I know people who happily have that arrangement you describe. It isn’t impossible.

  • Gia 16 weeks ago Reply

    This article has given me a sense of satisfaction that can’t be described but as pure happiness. I was courted by one of these men who was able to be in love with multiple girls, I had always wondered why. Even years later when we went our separate ways. He has now come back into my life and I’m overjoyed. I can now date him whilst he’s dating more women and not feel bad or guilty. Thank you haha you gave me a sense of “it’s okay”. I thought I was a freak for being okay with him dating me and another. We can now all be happy and in love. <3

    • Charlie 16 weeks ago Reply

      So happy to hear that Gia! More than anything I think it’s great that people are becoming more comfortable living the lives and having the types of relationships they want as opposed to feeling like they need to fit some societal mold. If it makes you happy, I say go for it :-)

  • Ivan Manasuev 3 weeks ago Reply

    Hey Charlie, hope you can still read this even though it has been a while.
    I need your help man. I have been dating multiple girls for a while now and you have outstanding advice, a few new things I picked up.
    However this one girl I dated recently just f*cked me over a bit. She is one of those types that are ungrateful and have 0 sympathy, but are extremely outspoken.
    Little did I know she was like this, but even though I told her multiple times as we were in bed that this is nothing serious and that we are only friends, she gets really jealous and gives attitude whenever I am with other females.
    It got to the point where as a group we met up at a pub coincidentally, and she was giving so much sass and attitude that the girls I was originally friends with took her side in thinking I do not respect women and cheat on them.
    What do I do man? She is f*cking up my reputation and is really nice to me in person but not with others, and has quite some flames!

    • Charlie 3 weeks ago Reply

      So first thing is to sit her down and call out the behavior. Either she is under a mistaken impression that you’re cheating on her (in which case you need to be very clear that you aren’t dating and probably break things off) or she is purposely slandering you to be vindictive. You should be clear, but understanding if it is the first option, somewhere communication broke down and you need to make sure you’re on the same page. But if anyone calls you a cheater, call bullshit VEHEMENTLY. General life principle: be cognizant of people’s feelings and apologize for upsetting people even when you thought you were clear. But any time people question your honesty or your integrity, put your foot down hard. That goes for your female friends too.

      So if they accused me of cheating after hearing that girl’s version, I might say “I don’t know what she told you, but I absolutely was 100% clear with her and I 100% did not cheat on her because we are not dating. No grey area. I would never cheat. If you think I did, we have a bigger issues, because now my word is being questioned and I take that very seriously.”

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