Is It Okay To Sleep With Multiple People At The Same Time?

Is It Okay To Sleep With Multiple People At The Same Time?

It feels as though I’ve written several variations of this exact topic in the last month. Perhaps, it’s because of all of the conversations I’m having with friends about, if it is okay to sleep with multiple people at the same time when you are dating. A common question people keep asking my opinion on. In short, the answer is no, it’s not okay. More like, hell no, it’s not okay. But that’s too easy, and unrealistic according to the way some of my friends are living. 

One of the things that annoys me most is when someone complains to me about what they are doing wrong on dates, and why they are always the second choice. I sympathize with you if you’re a great person and really putting yourself out there. Being second best sucks. However, if you are like some of the people I know, and you are having sex with multiple people–  there is your answer. How can anyone take you seriously when you are spreading yourself so thin?

I understand taking time to get to know someone. What I don’t understand is not being honest when you are sleeping around, and investing time into different people. I can’t speak for everyone, and both men and women are equally guilty, but for most of us– we would rather the person we are hooking up with be honest. I want the choice to continue sleeping with you if I know you are intimate with other people. Versus being made to believe I am the only one you want.  

When you respect yourself enough to be selective about who you get into bed with, you are also respecting your partner. I don’t believe people who are promiscuous are looking for anything serious. I don’t condone anyone’s right to be promiscuous. However, I think there should be a level of honesty when you are sleeping with more than one person. There are too many risks involved: STD’s, pregnancy, emotional attachment, trauma, to not be fully transparent. Last week a girlfriend of mine told me she was sleeping with seven different people. SEVEN! I’m sorry, but what? Who has that kind of time to meet seven people regularly, sleep with all of them and keep them separate? I can barely multitask two different conversations on a dating app. Girls got skills. 

My girlfriends aren’t the only ones calling to talk my ear off about another guy that blocked them on social media, or ghosted them. My buddies are experiencing similar hangups with women. Two days ago a buddy called to tell me that his emotionally unstable girlfriend didn’t trust him. Turns out after they committed to a relationship, she discovered he was pursuing and sleeping with multiple other women when they were dating. The only way to move past this argument was for him to commit to just her, which caused her to force him into a relationship, and him to promise things he couldn’t deliver. Great way to begin a new relationship, by starting out with lies. It seemed like an obvious answer when both my girlfriend and buddy were asking me advice about the same thing– don’t sleep with multiple people, and don’t lie about it.

Both were oblivious. Neither one of them saw the domino effect of sleeping with different partners when you are dating. This is where it gets tricky. Women are not like men. Our brains don’t function rationally all the time. Men are great at compartmentalizing, but women have a tendency to tie everything together. When he says, “I just want to be friends.” but he calls daily, sends sweet texts and asks us to come over for a “sleepover,” we think he is into us. And if he’s not ready now he will be eventually. A man thinks when he’s honest he’s in the clear, but unfortunately your actions are not saying the same thing as your words, and we are reading your actions

The same is true when women fail to mention that they are looking for something serious and allow men to treat them like a bootycall. There’s a good chance we think you are totally into us when you keep calling and making the effort to see us. When nothing becomes of it, and we accept that, it’s on us for allowing it. Women are guilty of misleading men too.

Another common dating mistake I see is when someone doesn’t know what they want so they keep their options open. Then, when the right girl/guy comes along, they want to lock her/him down. When it’s not mutual they keep playing the filed until the person they want to commit to them does, or they find someone else who will. It’s an insecurity thing for some people, and convenience for others. It’s also a sign you need to practice self love.

I don’t think it’s bad to have casual relationships as long as everyone is on the same page. I do think it creates a lot of confusion and dating complications when you are not. Which is why it is always best to be honest. I realize you can’t predict when you are going to have sex on a first date, or if that is going to turn into a second, third or fourth time. However, if you are doing this with multiple people you owe it to the people involved to be honest. Or choose one to get serious with. If you don’t feel comfortable telling someone you are sleeping with multiple people at least tell them you are dating. If they are confident enough to ask you straight out if you are sleeping with someone else, please be honest.

From all of my dating experiences, I’ve never been angry with a man who was honest. I have been disappointed by someone who mislead me to believe they were someone different though. Feelings are important and you should acknowledge when someone has feelings for you that you cannot reciprocate. It takes courage to do the right thing, and a coward to be selfish. If you are looking for something serious be honest about your intentions. If you are not looking for a relationship lead with that foot. You can happily meet someone who is looking for a one nightstand or someone seeking a relationship. You’ll never know until you communicate what you want, and be honest with yourself if you can be what they want.



is the CEO of She also works as a Creative Director, Writer, Brand Strategist and Fashion Editor.

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