The Pros & Cons of Dating Multiple People While You’re Single


I was in the midst of rereading my second book Single Woman Chronicles: An Atlanta Love Story…Kinda, and I came across an interesting point. The book is a fiction about a young lady navigating dating in Atlanta. In chapter 1, she gives rules to how she operates while being single. One of her rules was to date as many people as you can juggle at once. This made me think “Is this actually a good idea?” Although the book is fiction, the character is very similar to me in my early twenties. Back then, I was like an NBA team. I had a starting lineup, some bench warmers, and I was always looking to draft someone new just in case a few players decided to drop the ball. I had a winning team and I enjoyed my single life to the fullest. Or did I? Several people date this way, and for some people it works. But now that I am close to 30 and I have seen what it looks like to have a team and to be completely alone, I have a full view of the pros and cons of dating multiple people while you’re single.

Before I jump into the list, the pros and cons will be different for everyone because it all depends on what you want out of dating. Is your end goal a relationship? Do you just want casual encounters? Or do you have absolutely no idea what you want? Once you answer that question, then you can decide if dating multiple people is for you. In the meantime, here are my pros and cons to dating multiple people while you are single.


  • You discover what you want and what you DON’T want…When you’re dating multiple people, the process moves quickly. Your life sort of becomes a speed dating event. You meet someone on Monday, go out with them on Wednesday, find out they suck on Sunday, then the process continues. During this process, you get to see the things you really like but also the things you absolutely hate. When you’re dating several people at once, you have to use your time wisely. There is usually one person who you want to spend most of that time with. That’s usually your MVP. That person possesses the things you like. But then there’s that bench warmer that you only text when you’re extremely bored and have absolutely nothing to do. I’m talking about NOTHING to do. You have washed and folded clothes, shampooed the carpet, reorganized your closet, but you’re still bored so you text this person. This is the person who possesses the things you hate.

Contrary to popular belief, having multiple people at once doesn’t fill the void of loneliness

  • You learn the rules of dating…I would love to say dating is black & white but it isn’t. It’s the biggest gray area ever. There are some twisted rules that you will only learn by experiencing. 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 are single. Twisted stuff, I know but you will learn these types of things if you date a lot. It’s just like having a job or learning a new skill; the more you do it, the better you get at it with experience.
  • You become wise quickly…When you’re dating several people at once, you begin to notice the games people play. You start to recognize patterns so when someone tries to run that game on you, you know you need to shut it down. When you are fresh 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. Don’t get me wrong, with learning lessons comes some sort of emotional pain. But it would be a lot worse if you were deeply in love with someone rather than when you have four other people to fall back on.


  • You feel lonely…Contrary to popular belief, having multiple people at once doesn’t fill the void of loneliness. You can have someone lying next to you and still feel alone. This is because when you’re searching to fill that void, it’s a soul connection you’re looking for. You are searching for something to complete a deep gap in your emotions. Dating several people at once won’t do this because these are all shallow connections. It’s hard to get deep with someone if you’re dividing your emotional pie by five. This is why I tell people who want a relationship or marriage not to do this. It is okay to go on dates and get a feel for people. But to intentionally date several people at once is counterproductive to the process of dating for marriage. It just leaves you confused and empty. The process is also very volatile. Just because you have five people in rotation, doesn’t mean you always have someone to call when you want to hang out. There were several times that I ended up on my couch drinking wine and watching Insecurebecause all of my guys were either busy or had been cut off. The process moves super quickly and it’s hard to find a quality team.

You lose sight of what could actually make you happy because you are constantly getting a temporary high by being in the presence of casual people.

  • You lose sight of what you want…When you are talking to several people, it gets hard to focus on what you want. You lose sight of what could actually make you happy because you are constantly getting a temporary high by being in the presence of casual people. It is a fact that humans crave physical touch. It is something we can’t live without. But if you have not trained yourself to be able to be content without that physical touch, you will constantly be enticed by casual encounters rather than holding out for a soulful encounter. When I was dating several people, I would think I wanted a relationship but as soon as someone I liked said “Oh, I’m not looking for anything right now”, I convinced myself that I wasn’t either. I rationalized because I had several other guys so I must not want a relationship right? When you have five different people telling you five different things, you begin to lose sight of why you’re dating in the first place.
  • Your emotions become unstable…Most people have the false belief that when you juggle several men or women at once, you won’t get attached to any of them. HA! That’s hilarious. You will definitely get attached to someone and when you do, it will be hard to adjust. 1) You will think they’re like you and that they have a team to so you’ll be very paranoid and could self-sabotage. 2) You will be confused about what to do with the other people you’re dating because you want this person but at the same time, you don’t want to risk putting all your eggs in one basket. 3) If it doesn’t work, you have no idea how to cope so you just go back to the same thing you were doing before, resulting in emotional baggage that will be carried on into another relationship. (Or in your case, a situationship.) Stop thinking you can spread your emotions out to prevent yourself from getting hurt. It actually makes it worse.

The reason most people date this way their whole lives is because they are looking to fill a void no man can fill.

  • You become dependent on people for your happiness…Let’s be completely honest here. If you are knocking on 30’s door and you still date this way, it isn’t because you’re looking for something casual, it’s because you fear being alone. Don’t be ashamed, that’s like 90% of the population. People have become so brainwashed into thinking you have to have someone in your life at every waking moment that they fail to realize being by yourself actually gets them closer to a stable relationship. If all you’re used to is having multiple people around all the time, then being 100% by yourself will scare you to death. But fear not, God is with you! When you finally let go and let God, you will find that being 100% alone is the most stable you will ever be. You stop being dependent on the presence of people for your happiness, and you start depending on God to heal your dark places so you can find happiness. The reason most people date this way their whole lives is because they are looking to fill a void no man can fill. Filling this emotional void will take time, but that time consists of being completely by yourself. Having people around only distracts you from facing the pain that caused this void in the first place. You must eliminate distractions and focus on fully healing so you can be happy alone. Stop running from your healing. Get to the bottom of it so you can fall in love in a healthy, stable way that fills your soul, not just your flesh.

As you can see, there are good and bad things to dating several people while you’re single. To each his own. But if I had to give a strategy, I would say do this in your younger years. When you’re fresh in dating, it’s dangerous to commit one person too quickly without fully knowing how this dating thing works. In high school and college, it is okay not to put your eggs in one basket. But when you start creeping up in age, it becomes a bad habit and an excuse to avoid being lonely. This type of dating should only be temporary in order for you to learn what you want and don’t want in a mate along with how to navigate in the dating world. Once you get the hang of it, you should stop dating this way and aim for more stability. This means being alone until you find someone worthy of your focus. While you wait, you should spend time getting to know yourself and healing your dark places. But again, this is just my opinion that I have derived from my own experience. But remember that casual encounters only satisfy you temporarily, it will take a soulful encounter to satisfy you forever.

Get your copy of my new book today! Click here to purchase.

Facebook Comments

No Comments Yet.

What do you think?

Your email address will not be published. Required fields are marked *