Single- Dating Multiple Women

How to Do it With Integrity

By:  Jessica


Contrary to what you may think, women are indeed kosher with you dating several of us at a time.  What we are NOT, I repeat, NOT tolerant of is you lying or deceiving us about it.  What this is more about is your own discomfort with being forthcoming and fearing the possible outcome than the act of playing the field itself.  I have spoken with many women on this topic and want to share with you some of the general consensus about how to do this with class, integrity and character.


It is a bit irrational to think that those in the dating world should focus on only one person at a time and they should not entertain other candidates.  However, there are those individuals that prefer this method and have a difficult time juggling more than one prospect at a time.  There are women who may judge you if you decide to date multiple people and may opt not to date you if that’s the case. Let that be ok.  If she’s struggling with not being the only one in your dating world, then I’d wonder about how secure she really is and how realistic her expectations are.  Let the women who want a monogamous dating experience seek a man who prefers to operate this way too.  This is neither a good nor bad preference, it’s simply a personal preference.


Now for those of you who prefer to keep your options open until you meet a woman that you want to see more exclusively, then read on.  Women date multiple men as well and those who do it best follow some basic rules:



It’s imperative that you are forthcoming about your situation.  I’m not suggesting that you need to announce this fact as a part of your opening shtick, but if and when the question comes up, tell the truth about dating other women.  This honesty includes not omitting this information or alluding to something different if the topic comes up.  Here’s the reasons why this is so important:

Trust and Character

You are setting the stage for the remainder of your exchange with her and if you are dishonest out the gate, it is shaky ground to begin on.  Regardless of whether this is a woman that you see yourself with in the future or if she never found out, this is an essential component of being a man of character.  You want to be known as an honorable person and this is an opportunity to demonstrate your trustworthiness.  If you’re ok with it, then there’s a better chance that she’s going to be ok with it.  When you’re sketchy and deceitful it gives the sense that you’re insecure with your choices and are not acting as a confident and assured man…(a serious turn off).


Aside from this, if she is a person that you have a crack at in the long term, when (and trust me, she will find out) she uncovers that you were dating other women and you lied about it, she’ll begin to question the fabric of your integrity during the whole course of your relationship.  It sends unnecessary warning flags of mistrust and danger that simply degrade the kind of safety and honesty that solid relationships are built upon.


I once had a situation where I was having a casual dating relationship with a man long distance and though I made it clear that my personal policy was not to sleep with men while they were sleeping with others, he omitted his sexual exchanges with another woman.  I didn’t expect him not to sleep with others (we weren’t exclusively dating), but I did ask him to be forthright about it.  When I found out I was more impacted by his dishonesty than his natural sexual urges.  Since this was someone I truly cared about, had he been honest I would have even been willing to re-examine the boundary that I had set and considered making a different agreement.  However, his untruthfulness turned me off and questioned my trust for him.



When you’re dating and potentially sleeping with multiple women, there are health concerns that everyone involved needs to be aware of.  We live in modern times when birth control and STD protection is readily available and can give all parties options for protection.  However, if you are not being truthful about having multiple sexual partners, this has implications for everyone’s health and wellbeing and can simply be dangerous.  Omission or deceit about health and diseases is a serious matter and one that you need to consider deeply.  Yes, even if it means that she decides not to sleep with you while you’re involved with others.  If that’s the case, you can look at this as an opportunity to immerse yourself more fully into the relationship you find yourself most interested in to make a better determination about your compatibility.


If you are forthcoming about your sexual life, you are giving her the option of making a decision that’s best for her, which may even include being comfortable with multiple bed partners.  Additionally, you are setting the stage and giving her permission to be honest with you about her sexual life and keep you in the loop about your own health and safety.  Everyone wins.


So, how do you do it?

When the topic arises about whether you’re dating others, simply say “yes”.  You don’t have to share lots of details (in fact, it’s preferable that you don’t).  Even if she pressures you for more information, you can state that you’re open to meeting and sharing time with valuable people.  You can share your intention for either a casual dating experience or the desire for a long-term partnership, but once again, be honest.  This also gives her the sense that you’re in demand and that you’re valuable; that you’re not taking yourself off the market just because you’re out on a date with her.


Keep the multiple women talk to a minimum in the beginning.  If/when you two start spending more time together, the topic will likely arise again.  According to the nature of your relationship, she may ask again if you intend to continue dating others or if you’re desirous of exclusivity.  The “When to Become Exclusive” topic is an entirely different article that we’ll address separately.


For now, we want to support you in being honest, forthcoming and honorable.  How you handle yourself during these first moments are revealing about your nature and your integrity.  If there’s one thing that I’ve noticed in working on this site, it’s that women are craving and begging for men with integrity and have all but lost faith in men’s capacity to be trustworthy and respectful.  I invite you to be in a class of your own…doing so will quickly separate you from your less-than-educated and aware counterparts.