Everything You Need To Know About Dating Multiple People At Once

You may already be in a situation where you're dating multiple people at one time. If not, it's possible that you're curious about how this dynamic would play out in your life. A lot of negative light has been shed on the notion of dating a handful of people at once, but it's really up to you to define what you consider true cheating to be. As you navigate this modern dating world, no one else's opinions matter more than your own. 


Going on dates with new people you meet is supposed to be a fun and enjoyable thing to do. Unfortunately, it can become a stressful hot mess if you don't know the ins and outs of how to date multiple people simultaneously in a manner that allows you to live your best life. 

There are tons of arrangements you can strike up with people who are open-minded. Conversely, you can take specific routes to maintain your privacy if you don't want your romantic behaviors to become public knowledge. Is this relationship technique right for you? Let's dive deeper into everything you need to know about dating multiple people at one time.

You have to define what you believe cheating is

If dating multiple people is your vibe, it's up to you to define what you believe cheating to be. When you're getting to know different suitors in the dating world, there's no shame in splitting your time between partners to enjoy various activities on different nights of the week. This is especially okay to do if no one you've been spending time with has attempted to lock it down in an exclusive and monogamous relationship. 


As long as no one has had that serious conversation with you about defining the relationship, you aren't technically cheating on anyone. As soon as one of the people you're dating tells you they want to become exclusive, you'll have to decide if you're ready to cut off the other people on your roster. If you're not ready to cut anyone else off, you might consider continuing to date the others on the low. Being cheated on can impact your brain, so it's important to navigate this situation cautiously.

You might also think about starting an open dialogue with the person who's ready to become exclusive with you. You can tell them you're happy to keep exploring your blossoming romance, but you're not yet prepared to become 100% exclusive. The question remains ... how do you personally define cheating? Is being the instigator of infidelity going to make it difficult for you to live with yourself because of potential guilt and shame? These are questions you'll have to ask and answer within.


Mixing up names and details is a possibility

When you're dating multiple people at one time, it wouldn't be surprising for you to accidentally mix up their names and details along the way. Your Tuesday night date with John to the bowling alley and your Thursday night date with Jacob to the miniature golf course will possibly mesh together in your mind. John might've shared a funny joke at the bowling alley, but the next time you see Jacob, you could mistakenly think Jacob was the one who told you something so hilarious. 


If you bring up the joke to Jacob, he'll be beyond confused because he'll have no context or understanding of what you're talking about. Things can get really messy with name-calling if you are unable to keep up. It's way too easy to offend someone who cares about you if you accidentally call them the wrong name at any point in time — especially in the bedroom. For these reasons, people who date multiple partners usually rely on pet names like babe, sweetie, and honey to stomp out the confusion.

Getting caught juggling your relationships can happen

As scary as this might sound, it's often true that everything that happens in the dark eventually gets exposed to the light. That being said, whatever secrets you might be harboring likely won't remain under wraps forever. Getting caught juggling your relationships is a very real possibility to be aware of. You might not want to assume the worst or expect terrible outcomes while you're having fun, but when you're entertaining different relationships, multiple people with very real emotions will inevitably be impacted by your actions. If one of the people you're dating is starting to feel jealous or possessive over you, they might do a little digging to find out if you've got anyone else romantically in your life. 


Some folks who are deeply passionate about their relationships are willing to go to any lengths to discover the truth. If one of the people you're dating sees a message from a different romantic partner pop up on your phone screen, that will give you away. Slipping up on significant relationship details is a glaring red flag too. Getting caught on a date with one of your partners can occur if you frequent the same establishments as each of the people you're dating. Becoming unexpectedly surprised in a more intimate space (like your bedroom) is liable to happen if your different partners have each spent time with you at your home.

Being honest might get you dumped

Honesty is generally the best policy to follow since no one enjoys being lied to. When someone lies to you, you're often left feeling betrayed, bamboozled, and hurt. It's hard to regain trust for someone who's broken your sense of trust in the first place. For these reasons, you might want to approach your intentions of dating multiple people at once with pure and brutal honesty. Just keep in mind that this route might possibly get you dumped. It's feasible that one or more of the people you're dating won't be able to handle the truth. 


If they find out that you've got multiple relationships going on, they might be way too offended to stick around. There's a difference between dating a roster of uncommitted partners and dating a handful of people to whom you've directly committed yourself. Depending on your individual situation, you'll have to gauge how much honesty you're willing to bring to the table. Honesty, regarding a hot topic like this one, might not yield the results of your dreams if you don't want to lose anyone you're dating.

Being honest might open the door to a polyamorous situation

Laying all your cards on the table may be the best plan of action for you if you are dealing with super open-minded people. If you tell the truth about dating multiple people at once to your partners, you might open up the door to a polyamorous situation. People who consider themselves to be poly have decided they want to opt for an ethical non-monogamous approach in the dating world. Being ethically non-monogamous means giving total honesty to all parties involved. 


If all the people you're dating are aware that you prefer keeping things polyamorous instead of monogamous, no one will feel as though they're being deceived. It also gives them the opportunity to decide whether or not they want to date other people along with you as well. If everyone feels free to date whoever they want, no one will end up accusing someone else of infidelity or stirring up negative drama. It's vital to make sure that solid rules are in place when entering a polyamorous relationship, so everyone feels that their needs are being met.

Dating multiple partners will keep your calendar full

The days of you having an empty calendar will be long gone if you decide to date multiple people at once. When you have a handful of partners to entertain, your calendar will undoubtedly be filled constantly. In order to make enough time for all the people you care about, you're going to have to figure out how to divide your time and attention in a way that allows everyone to feel equally fulfilled without burning you out. 


You can create a repetitive schedule with your partners that include seeing the same person on Mondays and Wednesdays while seeing someone else on Tuesdays and Thursdays. During the weekend, you can mix things up based on whatever might be going on. If you don't create a repetitive schedule for yourself and your partners, you'll have to ensure you aren't double-booking yourself by arranging plans with more than one person in the same time slot. 

When you have multiple people to spend time with, it might be a bit challenging to carve out any alone time for yourself. Quality alone time is still very important to have, which means you should certainly keep that in mind if this style of dating is your vibe.


Dating multiple partners can be a financial burden

Depending on the types of dates you're choosing to go on with your various partners, dating multiple people at one time can become somewhat of a financial burden. Suppose you're the type of person who prefers to trade off on who pays for dinners, or you're comfortable fronting the bill on fun excursions on a regular basis. In that case, you'll end up spending a lot more money than you typically would if you were just dating one partner alone. 


This is also an important factor to consider when it comes to celebrating your different partners on their birthdays and other holidays. If you intend to splurge on one, you'll probably want to splurge on the others too. The financial burden of dating multiple partners might not be a strain for you at all if you're the type of person who prefers to be spoiled and taken care of by the people you're with.

Deciding whom to celebrate holidays with can be stressful

Holidays can be a very tricky thing to navigate for people who are dating multiple partners at once. Major holidays for relationships, like Christmas and Valentine's Day, can get incredibly complicated if you have to figure out which one to spend your valuable time with. This is more of an issue for people who are doing their best to keep their romantic behaviors as private as possible. At the end of the day, though, you'll have to decide whom to prioritize when big holidays roll around. 


If you spend one too many holidays in a row with one of your partners over another, it will possibly expose the setup you've arranged for yourself. If you're in the type of situation where it's easy for you to be open and honest about your current situation, you can do your best to split your holidays up so you'll be able to see everyone you care about before the sun sets.

Your friends and family may have preferences for one of your partners over another

When you date someone new, introducing your significant other to your friends is usually an exciting experience. On the other hand, introducing them to your family members is a little more serious. If you decide to introduce multiple people you're dating to your friends and family, it's very possible that they'll gain a liking for one more than another. Once your friends and family begin to build a preference, their opinions will start rolling in and potentially influencing your decisions. 


At the end of the day, it's up to you to decide who you want to spend the bulk of your time with. Since you're putting your friends and family members into a position where they'll be able to compare however many partners you're dating at any given time, receiving their feedback sort of comes with the territory. Introducing your friends and family to the people you're dating is a totally normal step to take as your relationships progress, regardless of how many people you choose to date at once.

You won't find yourself getting bored easily

In the same way that it will be very difficult for you to find an empty day on your calendar, you won't find yourself getting bored while dating multiple partners at one time. It's far more challenging to experience feelings of boredom and loneliness on a random evening if you've decided to date several people. Plenty of folks who are single or dating one person monogamously understand that boring days will roll around every once in a while


When you're single, you have to go out of your way to meet up with platonic friends or be willing to take yourself on solo dates to enjoy your time. When you're dating one person monogamously, you have to be patient with them and what their schedule will allow you to do together. On the contrary, dating multiple people means you will have unlimited opportunities to arrange various date nights and plans whenever your heart desires.

You won't expect all of your needs to be met by one person

It may put a lot of pressure on your partner's shoulders if you expect all of your needs to be met by them. It could certainly alleviate a lot of emotional and mental strain if you conclude that the different people you're dating can fulfill your various needs.


You can enjoy binge-watching reality TV shows with one of your partners whenever you're together if your other suitor considers reality TV to be trash. You can ride exhilarating and thrilling rollercoasters with one of your partners at theme parks if the other is too terrified to try something like that. You can admire gorgeous scenic views on romantic hiking trails for great exercise with a specific partner if the other would rather hit the gym for a workout.

Instead of hoping that one person will fulfill every single need on your list, you can benefit from the different interests, hobbies, and personality traits each different partner brings to the table.

When you're ready, transitioning to monogamous dating might be challenging

When you're ready (if you're ever ready), transitioning to monogamous dating may pose a challenge for you after dating multiple partners. When you get used to having a busy calendar filled with exciting plans with different people all the time, your calendar might feel empty and barren after narrowing things down to one partner. When you get used to having all of your needs met by multiple people who each bring different unique qualities to the table, it might feel like the one partner you've chosen is unable to fulfill you entirely. 


Transitioning to monogamous dating after having multiple partners at one time simply won't be an easy thing to do. If the one person you've chosen to commit to monogamously is worth it in your eyes, though, you'll do whatever it takes in order to make it work. It's not impossible to successfully date someone on a monogamous level, despite your dating history. 

You might start comparing bedroom activities

As detrimental as this might sound, there is a chance that you begin to compare bedroom activities between the partners you're dating on a subconscious level. Without trying to compare anyone's physique, suaveness, attractiveness, and talent, your brain might constantly start bouncing back and forth in comparison mode. When you start picking up on one person's prowess and capability above another's, it can cause a serious shift in your level of interest and desire. 


Maybe drawing bedroom comparisons isn't a subconscious thing for you at all. However, it probably isn't appropriate to strike up conversations about all of your partners' skill sets in the bedroom with your closest friends. The best rule of thumb here is to put yourself in your partners' shoes. How would you feel if you were a fly on the wall overhearing everything they had to say about your expertise and confidence in the bedroom compared to other people they were sleeping with?

You shouldn't treat your relationships like ego boosts or games

The last thing you want to do while dating multiple people at one time is treat your relationships as if they're nothing more than ego boosts or manipulative games to play. If you only want to date several people at once because it makes you feel better about yourself, you probably aren't approaching things from the right headspace. There are many personality traits of cheaters, according to experts, and being insecure is one of them.


In fact, there's a reason why cheaters are some of society's most insecure members. People who are prone to cheating love the idea of having a safety net to fall into if things go wrong in their primary relationship. They also appreciate the sensation of being desired and wanted by many people at any given moment, even if they already get loads of attention and reassurance from their main partner. If you feel like this describes you, you might want to reevaluate your choice to date multiple people. Boosting your ego and playing mind games with others for the sake of your own conceit is a tad problematic.

You should deeply question why you have a desire to date multiple people at once

Before jumping into a situation where you're dating multiple people, you should deeply question why you have the desire to do something like this at all. There's nothing wrong with wanting to be with multiple partners if you consider yourself a polyamorous dater, which is perfectly ethical when honesty is placed at the forefront. If you prefer monogamous dating, though, and still want to entertain multiple relationships, there's probably a reason for that. 


There are several signs that may indicate that you aren't ready to get into a relationship. For example, some struggle with commitment issues and don't want to feel boxed in with one partner because they'll start to feel suffocated. If that sounds like you, you can address those emotions without feeling guilty or ashamed. However, it's important to do so before juggling relationships and possibly breaking someone else's heart. Conversely, some people have incredibly high sex drives and don't believe they will be satisfied with one partner alone. 

Having access to different people at different times of the week to achieve a sexual release isn't necessarily a problem, either, if you're being honest with yourself about your impulses. You might want to take a deep dive into your interest to juggle multiple relationships to figure out why this intrigues you. If your desire comes from a mentally healthy place, you don't have any reason to fret. If this comes from a place of toxicity, you might want to reassess. 


It's totally okay to keep your options open

At the end of the day, there's nothing wrong with keeping your options open. The more you date around, the easier it is to figure out what kind of partners you want to have in your life for the long haul. Each romantic experience you have will open your eyes to behaviors you adore and red flags you want to address. When you date multiple people, it helps you realize that you never need to settle for less than what you absolutely deserve and want. 


If one of your partners is constantly disappointing you and letting you down, it's easy enough to call it quits since you're possibly already dating someone else who knows how to show up for you in ways you genuinely care about. It's feasible that the exhaustion of juggling multiple relationships at one time might turn you off and make you feel empowered enough to enjoy a life of singleness for a while. Whether you decide to remain solo, date one person monogamously, or date as many people as you come across, you never have to feel like your options are limited.