The 8 Rules Of Dating Multiple People At One Time

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Dating multiple people at once
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Life is short, and we are all in a race to make the most of it. After all, you only live once. Due to the rise of social media and a surge of dating apps, more and more people are expanding their dating pool. Most people nowadays are dating more than one person at a time.

You go on a date with a person when you are interested in them and want to get to know them better. Dating is the probationary period where you figure out whether you two are suited enough to proceed to the next level.

While talking to more than one person on online dating is pretty common, things can get a bit convoluted when you date multiple people at once. Here are some rules that will help you sort out the tangles of casual dating, and how you can navigate dating multiple people at once.

The 8 Rules Of Dating More Than One Person

Dating more than one person is called “casual dating”, and if done right, it can be a lot of fun. After all, you are testing the waters and that’s completely fine. Yet somewhere down the road, some lines can get blurred and this causes unnecessary heartache.

“I was trying to find someone to be in a relationship with, but couldn’t decide between the women I had been going on dates with,” Mark, a 25-year-old marketing rep told us. Adding, “I didn’t know how to tell either of them about what was going on, so I didn’t. It felt wrong, but I didn’t want to stop either.

“Things kept getting serious with both of them, and before I could make my mind up, they found out about each other. Turns out they had mutual friends. I never intended to be dating multiple women, and I had no idea how to go about it when I found myself in that situation.”

Just like Mark, it’s possible you may have questions like, “Is it wrong to date more than one person?” or not know how to go about dating multiple women at once. Before things fall apart as they did for him, it is in the best interest of everyone involved to follow certain dating etiquette.

When you are dating multiple people casually, you need to know that it’s a normal thing to be attracted to multiple people at once. However, what you do about it makes all the difference. Let’s take a look at the rules of dating multiple people at once.

Related Reading: 20 Signs He Wants More Than Your Friendship And Not A Casual Relationship

1. Honesty is important while dating more than one woman or man

Honesty is the building block of any relationship, and that includes casual dating too. If you are going to date more than one woman at a time, it is best to let all those involved know about it. All the parties deserve to know what they are getting into. It is unfair to give someone the illusion of exclusivity for personal gain.

However, honesty does not mean you give all the details of your dates with other people to the woman in front of you. What happens on your date, stays between you and your date. You want to impress them enough to make her want to go on more dates and too much information might ruin your chances of that.

2. Always be respectful of others’ feelings and choices

dating more than one woman
It’s better to talk things out

Not everyone is comfortable with the idea of dating and sleeping with more than one person at a time. A large part of our society fixates on monogamy. The idea of “the one” is a by-product of such a world. So, it is little surprise that many people avoid polyamory or even casual dating.

While you might be perfectly fine with dating multiple women simultaneously, the person you want to date might feel differently about it. Maybe s/he believes in twin flames and soulmates. Perhaps s/he doesn’t approve of premarital sex and is saving themselves up for after marriage. It’s possible s/he doesn’t care if you have sex on the first date. No matter the school of thought, we have to be respectful of people’s feelings and choices. Consent is queen!

3. Know your reason for dating more than one person

There are multiple reasons why one would opt to date casually. A bad breakup, a toxic relationship, you want to focus on your career or maybe you are polyamorous are some of the reasons why you would want to have a large dating pool. And it’s completely fine.

However, you need to figure out whether you want to do this long-term or if this is just something you want to do for a while. The most important etiquette for multiple casual dating is transparency. Letting your dates know where you are on the dating front will save everyone a lot of anguish.

So, it’s not wrong to be on multiple dating sites or even to be talking to more than one person on online dating as long as you’re honest with yourself.

4. Don’t make it a competition

With little commitment comes little responsibility. That’s the best part of casual dating. You meet new people. You go out and spend time having fun with no strings attached. Casual dating is supposed to be pleasurable due to the lack of complications. However, some people turn casual dating into their own personal version of The Bachelor.

They pit their dates against each other and thrive in their jealousy. Such people use attention to feel better about themselves. This is especially the case if you’re in a poly relationship. If you can’t handle him dating multiple people or if you want her to know when to stop dating multiple guys because the comparison is getting to you, it’s important to let them know that.

When you’re on multiple dating sites, you might find yourself guilty of this behavior as well, since you’ll probably be comparing your matches with each other. Try not to beat yourself up about it, but make sure you’re not indulging solely to boost your ego.

Related Reading: 13 Signs A Man Is Falling In Love With You

5. Talk deal-breakers when dating and sleeping with more than one person

William and Scarlet liked hanging out with each other. They had a lot of common interests and their priorities were similar too. William was attracted to Scarlet and wanted to ask her out. He asked if she would be willing to give them a chance. He proposed they go for a few casual dates to see if they suited each other. If things didn’t work out, they could always part ways and remain good friends.

Scarlet was skeptical. She had just come out of a 3-year long relationship because her boyfriend had cheated on her with one of her close friends. The experience was humiliating for her and it had taken a long time for her to get the betrayal out of her mind. Even though William was nothing like her ex, she was still wary. So, she put down her conditions.

Scarlet told William about her qualms. She said “Will, I do like you, and I would love to go out with you. I am also ok with us seeing other people as well. However, there is one condition. You cannot date any of my friends or family. That is a deal-breaker for me. If you do get attracted to any of my friends, do tell me so that we can end things between us. I won’t be upset.”

Will agreed to the condition and they started dating. Will and Scarlet have been going steady for 6 months. They are exclusive and Will is planning to ask Scarlet to move in with him.

Infographic on The 8 rules of dating multiple people at one time
The 8 rules of dating multiple people at one time

6. Have an “N” dates rule

It can be the 5th date or the 8th date but keep a fixed number. If you have been on a date with the same person “N” number of times, then it’s time to have the talk. Maybe you really like the person, then you can talk about exclusivity. Perhaps you don’t feel any chemistry yet with the person, then it’s time to move on to other people.

The idea behind this rule is to check in with your date about where things are heading. Spending a lot of time with one person can give rise to feelings. So, it is vital to talk it out with your date. It doesn’t really have to be about taking the next step. If you have commitment issues, then say that. But do communicate.

When this rule is not followed, you might cause a lot of heartache to everyone involved. You won’t know when to stop dating multiple guys or girls, and the longer you avoid this conversation, the more complicated things are going to get.

If you’re at the receiving end, you’ll solely rely on trying to spot the signs s/he is dating multiple guys or girls to be able to figure out what you’re going through. If you do spot the signs like a growing disinterest or social media stories that suggest them dating other people, you need to make sure you put yourself first.

7. Realize and vocalize when you are in too deep

Change is the only constant in our lives. You might have started dating thinking you will keep things simple and uncomplicated. And before you know it you are head over heels in love. As Robert found out much to his surprise.
Robert and Ivy met in a theater group.

They were cast opposite each other and as the rehearsals progressed, so did their attraction toward each other. After the play was over, Robert asked her out on a date. Ivy was reluctant. She was very career-oriented and didn’t want to jeopardize her future. Robert suggested they just go on a few casual dates and see where things go from there. No strings attached since he too was moving on from a toxic relationship and was dating more than one woman. So, Ivy agreed to go out with him.

I like two guys. How do I choose? Quiz

One month into dating and Robert realized he had fallen for Ivy hook, line, and sinker. Since he was the one who had suggested casual dating to Ivy in the first place, he was petrified of telling Ivy how he felt. He tried to act cool and indifferent and spent more time with other people to no avail. Robert just couldn’t get her out of his mind. He had to tell her.

Meanwhile, Ivy was getting very upset with Robert. Everything was going perfectly fine and she had actually begun thinking that she could focus both on her career and Robert. Being with him seemed effortless. Then out of the blue, Robert started acting weird. They were not meeting up much and even the texts had tapered down. Ivy felt it was time to leave the relationship and move on.

Robert decided to call her and meet up over coffee. Robert told her everything about how the signs she is dating multiple guys got to him. He was shocked to hear that the feelings were reciprocated. He also thanked his stars that he had spoken up, otherwise he would have lost Ivy.

Related Reading: What Does It Mean When Someone Says They Are Looking For ‘Something Casual’?

8. Don’t kiss and tell: The #1 etiquette for multiple casual dating

“Mambo No.5” was a famous, catchy song that we all danced to, but did you ever give the lyrics a good listen? The song was primarily a man talking, rather bragging, about his exploits. However, in real life, nobody likes a person who brags. We are not asking you to hide the fact that you are dating more than one woman, in fact, you need to be open about that, but please spare everyone the details.

While you might be comfortable with having no secrets, your date might feel otherwise. Have a conversation regarding this early on. Discuss what you are comfortable with and what you are not comfortable with. And then proceed accordingly. If you are still confused, then just remember this – you don’t need to elaborate on any of the ‘W-H’ questions like “Who, When, Where, or How.”

Does Dating Multiple People Work Out?

Casual dating is the period before you become a girlfriend or a boyfriend. It allows you to get to know a person better before you embark on a committed relationship. If you’re unsure in your relationships, it gives you a chance to understand what you really want from your partner and from life. It is as much about figuring yourself out as it is about finding a potential partner. Below are some cases where casual dating is a good idea.

  •  You are attracted to more than one person at a time
  •  You get to determine if someone is the right fit for you in the long term
  •  You are not currently in a place in your life, mentally or career-wise, where you can devote yourself to just one person
  •  You are scared of commitment
  •  You are looking to be in an open relationship

Yet casual dating might not be everyone’s cup of tea. It’s not that you’ll find them constantly questioning, “Is dating more than one person cheating?” No. Their internal wiring is such that they are unable to focus on more than one person at a time.
Dating multiple people can only work out if you can compartmentalize. If this is not who you are, then casual dating is not for you.

Venessa explains how she thought she’d be okay with Jadon and her dating multiple people at once, but turned out to be quite the opposite. “I thought I’d be able to handle him dating multiple people when he first told me that’s what he’d like to do. I did not think I’d fall head over heels for him so quickly. The more I liked him, the more it bothered me that he was dating multiple people at once.

“Eventually, I had to tell him that this isn’t working for me. Thankfully, he agreed and decided that we can give exclusivity a try.” So, is it wrong to date more than one person? As long as there’s the consent of everyone involved, and as long as one person doesn’t start bragging about their sexcapades, it should be okay.

Related Reading: Casual Sex Is Great As Long As You Treat it Casually

When Should You Stop Dating Multiple People?

Often, it happens that a series of relationships gone wrong or bad breakups might make you feel it’s better to date casually. And you are not wrong to come to the conclusion, casual dating does help in such scenarios. However, if you do the things listed below, then dating multiple people might not be for you:

  • You tend to fall in love too quickly
  •  You are looking for labels and a future
  •  You like to have strong emotional attachments
  •  You get jealous quite quickly
  •  You are doing it because your partner is doing it
  •  You keep asking yourself is dating more than one person cheating?

If you are nodding to any of the above, then you should be true to yourself and not proceed with casual dating.

etiquette for multiple casual dating
It takes a few tries to find the one meant for you

To be honest, there is still a little stigma attached to casual dating and the reason for that is people confuse casual dating with polyamory. Dating more than one person is called polyamory as well, yet there’s one huge difference between them. While polyamory means being romantically and sexually involved with more than one person, casual dating is more about figuring out if the person you are attracted to is the one for you.

Dating, casual or otherwise, should not feel like you have to carry the world on your shoulders. It definitely requires work, but that’s not all it should be. It is supposed to be fun and make you feel happy. If you can maneuver the intricacies of dating multiple people, then well and good. But if you have to keep reminding yourself that this is fine, then listen to your gut feeling and don’t go through with it.

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