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Dating Multiple People – The What, The How & Everything Else

Dating Multiple People – The What, The How & Everything Else

Updated on Sep 13, 2023

Reviewed by Julianne Cantarella, MSW, LSW , Certified Relationship Coach

Dating Multiple People – The What, The How & Everything Else

Dating multiple people at once is fairly common now.

People either want to find love fast, or just don’t want to settle with one person. Whatever the reason might be, dating multiple people brings a lot of things to the table – good and bad.

So, the question still remains, is it okay to date more than one person at the same time? Let’s find out…

Is it cool to date multiple people?

Dating multiple people at the same time increases your chance of finding your most compatible partner. But you need to be sure of the purpose behind dating more than one person at the same time.

According to relationship experts, dating multiple people is not only okay, but it may also actually be beneficial. In theory, it is supposed to widen the pool of potential matches and also increase the probability of finding “THE ONE”.

Dating more than one person at a time allows you to have more fun, learn more about them as well as your own self (what works for you and what doesn’t).

As long as you are respectful of the feelings of the people you date (you’re not a “player” or a “sleepover”) and are honest about your intent, it is okay to date multiple people at the same time.

Dating multiple people rules

Dating more than one person at a time is definitely fun, but it’s also hard work (oh, life is so tough, right?).

Don’t struggle with the juggle because—we’ve rounded up a few pointers below, which will guide you exactly on how to handle the tricky situations that come with dating multiple people at the same time.

1. Don’t make a mess out of it

Do not date too many people at the same time. According to relationship experts, the ideal number of people you should date simultaneously is three. Anything more than that will make you confused.

You might not be able to process all the information related to so many people and thus miss out on the opportunity to connect with either of them.

2. Have a clear goal

Ask yourself this question “why do I want to date multiple people at the same period of time?” Is it because you want to increase your chances of finding true love, or are you just not yet ready for a commitment?

Make sure you do not date multiple people simultaneously because it is a trend among your friends. If you do not really want this but still do it under peer pressure, you’ll end up frustrated in the end.

3. Respect their privacy

Yes, of course, you want to know the person, but you can’t do it overnight. Plus, the more you know, the more attached you will get to them… and you wouldn’t want that.

Instead, respect their privacy and do not ask too many questions about them. Also, if you happen to learn something about them, try to keep it to yourself.

4. Set clear expectations

Right from day one, explain why you want to date this person. Do not hide the fact that you are dating other people too. Never let them get the impression that you two are exclusive. All the people you are dating should know about what you are looking for from this whole dating process.

 Do you want a long-term relationship, or are you just in for fun because you are commitment-phobic? Whatever the reason may be, talk about your intentions from the very first date to avoid future confusion and heartbreaks.

5. Do not overstep your boundaries

Set clear boundaries in your mind about how you want to go about this whole dating game. For example, consider what might be a deal-breaker for you when you date someone.

Unashamed disrespect, poor communication between you both, and inconsistency are a few examples of typical dealbreakers while dating people.

So, make sure to tell your date what the deal breakers look like for you, and do not hesitate to call it off if the other person indulges in any of them.

6. Remember you are not exclusive

Just like the fact that you are talking to multiple people, your dates may be dating other people too. You cannot expect other people to be exclusive with you when you are not! You cannot get upset if they start dating other people when they come to know about your choice to date multiple people.

Neither of you can force the other to commit. The best thing to do in this situation would be not to assume anything while you are into casual dating.

7. Respect their preferences

You should keep in mind that not everyone you date would be okay with the idea that you are dating other people apart from them too. If it happens that someone you are dating does not want you to date someone else, it’s wise to call it off.

Respect that person’s preference to date one person at a time. But also tell them that you do not wish to be exclusive just yet and want to explore other opportunities too. Never force yourself into something you are not prepared for.

8. Never turn it into a competition

Your dates do not need to know how one is better than the other. You do not need them to compete for your attention. That is just toxic. Respect the people you’re dating, and always remember that they are not obliged to get involved with you.

Just like you, they are in search of the right person for themselves, so do not forget that you need to woo them too, and not just wait to be wooed.

9. This does not guarantee a relationship

No matter how many people you date at the same time, it will never guarantee you the relationship you want in life. Do not be fooled by all the options you have. Other people are also in search of their perfect match.

So, even if they date you, it does not guarantee that they will fall for you. They might date other people and will evaluate all options before they settle for someone. Who knows? You might be just the other option for them.

10. Never feel guilty

As long as you have declared your intentions and revealed to your dates that you wish to meet other people too, there is nothing to feel guilty about.

If it so happens that you feel that you have cheated on someone, it simply means you might have developed some feelings for that person.

One of the other reasons you may feel guilty is you are not okay with the whole idea of dating multiple people at the same time. You might have started it because it is trendy, but now your moral values are not in your support, and you feel guilty. Do not continue if that is the case.

11. Have a life outside of dating

Dating multiple people is a time-consuming affair. You get too busy with your interaction with all these new people that you actually miss out on the more important aspects of your life, like your family, friends, career and your hobbies.

If you devote all your attention to dating, you will be at a loss when nothing comes to fruition and you will feel frustrated for all the time that you have lost. So, the ideal thing would be to date a couple of people and still manage enough time for yourself and focus on things other than dating.

12. Know when to pull the plug

Well, you cannot go on dating so many people forever. There will be a time when you will need to stop and get off the dating express. Set yourself a limit like after “x” number of dates, I would have enough information about the person to decide whether I want to continue with them or not.

So, once you have been on your “x” number of dates, decide whether you want to continue with this person. If not, be upfront about it and explain it to them. Knowing when to stop is crucial when it comes to dating multiple people.

13. Do not play with people’s emotions

The whole purpose of dating is to find the perfect one who would reciprocate your feelings. So, in the course, you might find someone falling for you. But if you do not feel the same way about them, it is always a good idea to let them know.

It is toxic to encourage someone’s emotions for you when you are sure you are not really interested in them. If both of you want different things from each other, it is always a good idea to part ways.

14. Do not overcomplicate it with sex

If you get involved in sexual intimacy, it unnecessarily complicates things. People usually introduce sex in their dating lives when they are sure about the “one” person.

But when you do get sexually intimate with someone while dating other people, it might lead to confusion and jealousy and mess up everything for good.  

If at all you decide to sleep with other people while dating someone, make sure you are honest about it and use proper protection for your own safety and for the other person you are dating too.

15. Set different dates for different people

Do not overbook your day and invite unnecessary confusion in your life. Going out with more than one person on the same day will clutter your mind, and you will not be able to focus on either of them properly.

You do not want to think about the next date while you are already with someone or think about how your previous date was when you meet the next person.

Not to mention, the complications that may arise if the two people you are dating bump into one another! So, always set different days to go out with different people.

16. Do not overshare

You are not in a relationship yet with the people you are dating. So, don’t give out too much information about yourself to them as this is a sign that you’re “serious” about them.

And if this doesn’t work out, you’ll be just another goss-topic for them.

17. Be clear in your head

When you date multiple people, it is easy to lose out on your “What I want” in the process. Always have a clear picture in your head about what your expectations are from dating all these people; how would you go ahead if you fall for one of them?

The answers to these questions will determine your approach toward the people you date. You need to be clear in your head, be honest with yourself and with your dates to avoid heartbreaks and confusion.

18. Never brag about your experiences

Nobody likes a person who brags. While you should not hide the fact that you are dating more than one person, you should not also brag about your “achievements”. Keep the details to yourself.

Also, your date might not be interested to know about your previous dates. You do not need to keep secrets, but you do not necessarily divulge all the details about every person you’ve been on a date with.

It is quite disrespectful to the person you are with as well as to the person you are speaking about.

19. You can fall in love

Even if you date more than one person, you can never rule out the chance that you could fall in love with one of them.

If something like that happens, you should express your feelings to them and stop dating other people.

In case you were dating just for fun and do not want to get involved in any serious relationship, yet end up falling for someone – you could just stop dating that person and continue dating others.

20. Know when to have “the talk”

Suppose you do want to find your true love by dating all these people; and you finally find someone you want to commit to – that’s when you need to have “the talk”.

If need be, take a break from them and see if you still feel the same. If at all your feelings persist, go ahead and express your feelings but do not expect anything in return.

Pros of Dating multiple people

There is absolutely no harm in keeping your options open – it may seem like a whirlwind, but dating multiple people at the same time might actually help you to find your perfect match sooner. Here is a list of 5 reasons why you should consider dating more than one person.

1. You are spoilt for choices

When you date more than one person at a time, you get the opportunity to meet new people and narrow down your choices.

You can weed out the kind of people you do not want to be with and increase your chances of meeting your “perfect match”.

Dating many people at the same time also makes the experience fun and helps commitment-phobic people to steer clear of the exclusivity of serious relationships!

2. There is no emotional dependency

It is always a good idea to maintain your independence because you might end up disheartened and even heartbroken if “that” someone turns out to be a bad choice for you.

Casual dating is better in this case because you meet many people and have very limited time for each. It is mostly about fun, and there is no emotional baggage when it comes to dating so many people at the same time.

3. You get to know yourself and be an inspiration

Each relationship reveals a different side to you. So, when you date several people at the same time, you understand your likes and dislikes; what you want and do not want in relationships. You often get to challenge your limits with different people.

Also, when you date more than one person at a time, regardless of what others may think of you – you set an example for others to not care about what people say and step outside their comfort zones too.

You inspire them to be brave and do what they choose to do without paying heed to societal norms.

4. You know the rules of playing the field

The more you date, the better you get! Dating isn’t all black and white. There are some twisted rules that you will only learn through experience.

For example, a guy can take you to dinner, let you meet his mom, take you to his brother’s wedding, and move in with you, but that doesn’t mean you are in a relationship.

Until he asks “Will you be my girlfriend?”, you will be single! It takes more than one dating experience to understand all the rules of the dating world!

5. You become wiser

When you date several people at once, you begin to notice the games people play and start to recognise the patterns. So, when someone tries to run that game on you, you know you need to shut it down.

When you are new to the dating scene with no experience, it is easy to stumble because you don’t know when someone is lying. But dating multiple people at once teaches you how to avoid several pitfalls quickly.

Cons of Dating multiple people

Dating someone is a great chance to get to know them. But dating multiple people carries social stigma and has always been frowned upon. Let’s see why.

Here is a list of 5 cons that come hand in hand with dating too many people at the same time.

1. Keeps you away from meaningful connections

When you date more people, you lose out on the chance to get to know them up close. You also do not get enough time to open up to them. You almost never get the chance to emotionally bond with anyone. This might not be a good thing if you have set out to find the love of your life!

2. You might not find your perfect partner

Dating multiple people will never guarantee that you will definitely find the love you set out to find. You might just meet too many bad matches and finally give up on the whole idea of dating completely.

3. Hard to let go

Fun things are hard to let go of; this is a fact. Meeting new people on different dates is thrilling, fun, and adventurous.

Most people find it hard to let go. Why would you stop when you are having so much fun? But was fun the only reason why you started dating multiple people in the first place? Think about it!

4. You might feel jealous

In a non-exclusive relationship, your partner may be dating other people too. You may date two or more partners simultaneously. But this doesn’t sit right with a lot of people. You or your partner might get jealous of each other’s other dates, which can create problems.

5. Might miss out on real opportunities

When you date too many people at the same time, you lose focus on what you were in search of in the first place. You might get so carried away with the fun and thrill of dating new people every day, you might actually miss out on the people who might actually be a very good match for you.

6. Not everyone will be supportive

Society has set rules for everything, dating and love included. As mentioned before, dating multiple people is always frowned upon.

But this doesn’t mean you cannot follow your heart but remember that this journey may not be so easy.

7. Might experience dating burnout

Dating too many people at the same time leaves you with no time to process your emotions. Also, after a series of failed dates, you might just get overwhelmed and feel burnout.

How to date multiple people?

When it comes to dating more than one person simultaneously, you need to keep a few dating etiquettes in mind to avoid goof-ups. These are simple practices and do not require much effort to follow.

1. Avoid dating people in the same social circles

Try to keep things tidy and mess-free. Dating people who know each other or who meet frequently can be a problem.

You don’t want to deal with awkward run-ins and confrontations. You should also avoid hanging out at the same restaurants, coffee shops, or bars as all your other dates.

2. Prioritize protection

Set boundaries for yourself when it comes to sex. Decide from the start whether you want to include sex as a part of your dating process or you want to stay away from it and only indulge in sex when you have found “the one”.

Also, if you do want to get sexually intimate with the people you date, make sure you follow safe sex practices and use protection to avoid any health issues in the future.

3. Be open to all possibilities

You are not the only one dating multiple people at the same time. So do not expect yourself to be exclusive to everyone you date.

Others may also go out with different people other than you. So always keep an open mind to get the most out of dating multiple people.

4. Live in the moment

Even if you see more than one person during your dating phase, make sure to be present at the moment with them. Enjoy their company and make sure both of you have a good time.

Do not overthink your previous dates or worry about your next one. Treat each date with the respect and attention it deserves.

5. Keep it classy

If you’re dating more than one person, you are bound to let people down a lot of times. Just remember to be classy about it.

If you’ve been on more than a couple of dates with one of the people you’re dating, don’t switch off your phone or ignore the calls of other people in your life. Do not ghost them.

It’s better to tell them beforehand if it is not working out with them and you would like to take a break. People handle disappointment better than bad treatment.

A word from ThePleasantRelationship

Finding the partner of your dreams is no walk in the park. Technology (dating apps) has made dating easier – you have access to hundreds of potential matches at the click of a mouse.

Whether you are into online dating or depend upon the advice of a relationship expert or a dating expert or all of them, you’re most likely to face the challenge of more than one potential match for yourself.

Dating multiple people isn’t better or worse than dating only one person at a time because each approach has its own pros and cons. If you can maneuver the intricacies of dating multiple people, then well and good.

Remember, it’s your heart that is ultimately at stake. Choose wisely!

Are you interested to know more about ‘Signs Of A Lazy Boyfriend ’ then click here?