Dating More Than One Woman At A Time: The Straight Talk

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Dating More Than One Woman At A Time

I don’t know how you got here, but it must be a hell of a story. 

In most cases, guys just find themselves dating multiple women at a time. In fact, I have never heard of a guy who just decided to do it. Maybe they are there; I don’t know.

So you are caught up between two women (or more), and you don’t know how to go about it. I’ll be honest with you, so stick around and learn a thing or two.

Is It Okay to Date More Than One Woman at a Time?

That depends. Are you okay with these women dating other men?

Even if you answered yes, what are your intentions? Are you dating them for companionship, or are you looking for casual sex?

Dating multiple people at once is called polyamory. But for it to be polyamory, you must have the consent of those involved. 

So if you are just doing it in secret, you are more of a player. Polyamorous relationships are acceptable; in most cases, the women you are dating are also dating other men. So you are all on the same page. 

If that’s your case, then maybe it’s okay to date more than one woman at a time. But if it’s not, then it’s not okay. 

How Do I Date More Than One Woman at a Time?

Dating multiple women at once is not as easy as you think. There is more to dating than going out and spending time together. 

And if all you’ve been doing is holding hands and talking, then sorry to burst your bubble, but you are not dating. Dating is consensual, especially in these times where there are open relationships, friends with benefits, and polyamory relationships. Before worrying about anything else, you must define what you have first.

Dating more than one woman is acceptable if you do it the right way. But first things first:

A guy taking a picture of one of his dates
A guy taking a picture of one of his dates

Work on yourself

I came across a mind-opening post the other day. It was something like:

“I used to find women on dating sites and go out with a couple at once. While I would be charming on the first and second dates, their reaction was always the same. They would ghost me after the third date, so I would keep a stream of new women to counter the loss. 

To be honest, my life was pathetic back then. I went to therapy and got myself together. I’m currently working and still going on dates, but the irony is that on the third date mark when women would lose their interest, most of them show more interest and stick around.”

This guy explained how he found himself dating multiple women at once. But that’s beside the point.

I am sharing this to show you the importance of working on yourself. This guy would lose women as soon as he met them. And when he finally worked things out, things changed.

You might be in a situation involving multiple women because something led to it. As I said, I have never heard of a guy who woke up one day and decided to pursue multiple women, unless he is a player.

The very first thing to do in this case is to work on yourself. 

Figure out if that’s what you want or if you just found yourself in that position. Take time to understand yourself so that when you decide to pursue it further, you are sure you are polyamorous and can comfortably handle a polyamorous relationship. 

Do your due diligence

If you opt for non-monogamy, then research it and follow the ethical path. Today’s world is accommodating. You are allowed to date as many people as you want, provided you do it right.

Start ]learning everything you can about polyamory relationships. There is more to that than juggling several women at once. You should know the rules and how to maintain the relationship.

Do it as early as possible before you are in too deep. 

Communicate with those involved

I advocate assuming non-exclusivity until you have that conversation. It’s unfair for someone to assume monogamy and hold you down for something you didn’t consent to. Actually, I believe in defining what you have first.

Going on dates doesn’t mean you are dating. You are getting to know each other and determining compatibility. That’s why I say don’t assume a woman is your partner because you have gone out twice.

A guy eating a watermelon along with his dates at the beach
A guy eating a watermelon along with his dates at the beach

I suggest bringing up the topic of dating on your third date. You don’t have to shoot it out in an awkward way. Be creative around it and know where the other person stands. 

And since you are having the conversation, why don’t you talk about exclusivity and be done with everything?

You can say something like:

“By the way, I’m not monogamous; I don’t know if you are okay with that.”

You are making an ill-advised move if you delay bringing it up and decide to bring it up later on in the advanced stages of your bonding. If they are not okay with polyamory, they will feel offended and betrayed. 

Some people prefer to know from day one, so you can choose it to avoid the “You didn’t say” conversation.

Though we should assume non-monogamy by default, it’s better to talk about it instead of letting a woman believe they are your only one. It’s not cool, especially for those who hold on to exclusivity.

It’s easier for polyamorous people to assume non-exclusivity than it is for monogamous people. 

To be on the same page, communicate with those involved and let them know, so they don’t feel they invested in something that was not there. 

Go for women who want the same thing as you

A polyamorous man can’t date a monogamous woman. It can’t work. There are numerous polyamorous women, so go for those who want the same things as you.

Apart from having the same goals, you both have your emotions in check, so you date intentionally. What I mean is, if you try to make things work with a monogamous woman or one who is figuring things out, chances are they will catch feelings and make things complicated.

But if you go for one with the same objectives as you, they know the rules, so you have an easy time and an amazing experience. Besides, they are okay with you seeing other people because they are probably seeing other people as well.

Important Rules When Dating More than One Woman at a Time

Important Rules When Dating More than One Woman at a Time
Important Rules When Dating More than One Woman at a Time

My coursemates (males) were having an interesting discussion in class before the lecturer walked in.

One said,

“I don’t know how you date multiple women at a time. I have trouble keeping one interested. How would I manage two? “

He was talking to a polyamorous guy, so I couldn’t help but eavesdrop. I really wanted to hear his answer.

The polyamorous guy was cool enough to feed our curiosity. The most important thing he mentioned was that there are rules for the whole thing. Rules govern the entire thing, and that’s how polyamory relationships survive. 

Some of these rules include:

  • Sexual and/or romantic non-exclusivity is not a deal-breaker in polyamory. There will still be limits, but the possibility of other relationships is kind of the defining characteristic of polyamory.

  • Informed consent is an essential element of polyamory. For instance, if a woman you went on a date with is monogamous and you told them of your status, they don’t have to consent to polyamory for its sake.

  • Protecting partners’ sexual health is essential. Again, it is an issue of informed consent. If a partner does not know what safer sex practices you use, they can’t give informed consent to have sex with you.

  • Communication is vital. You need to communicate about anything and everything.

  • Honesty remains the best policy. Be honest from the start and let the women know you are not exclusive. In the same way, allow them to express themselves. Let them make informed decisions. 

While these are some of the common rules, some people say there are no rules to polyamory. Provided someone knows you are not exclusive, the rest is history. Some live by that.

I also must say this: Like any game where each game has different rules, every polyamory relationship has its rules. The parties come up with rules and agree to follow them.

A man having a selfie with his two lovely dates
A man having a selfie with his two lovely dates

Dating Multiple Women at Once: Final Thoughts

Dating multiple women becomes a problem when you don’t know what you want and use these women as experiments. It’s also an issue when you do it in secret, so no woman knows there are others involved.

In all fairness, you also wouldn’t want a woman to treat you that way. I find it disrespectful. That’s why I believe in laying everything on the table after the third date.

I say the third date because, at this point, you know a thing or two about the woman, and they know some details about you too. Some talk about their exclusivity as soon as the first date.

Talking too long to bring the conversation up is a cowardly move.

If you are okay with your status, nothing should stop you from telling her your intentions. Most guys give the excuse of losing a woman when they talk about polyamory. But I would say you better lose her instead of leading her on to something she isn’t up for.

Better still, there are so many polyamorous women, so why don’t you focus on finding them from the start? This saves you a lot, especially if the exclusive talk gives you goosebumps.

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Over the years, Stephanie has had her fair share of dating experiences. While some turned out great, others weren't so great. She believes that relationships are meant to be fun, exciting, and full of laughter. She wants to help men and women become confident, attractive, and successful in their romantic relationships.