How to Date Multiple People at Once Without Getting into Trouble

When you’re dating, you might be dating around. It’s not always a slam dunk with one specific person to stick with, and maybe you’re just in a place where you don’t want anything too serious so having fun and keeping your options open is the main goal. Dating multiple people at once can get a little complicated, but if it’s the goal at hand here are some ways to do it without getting into trouble.

Be honest about your intentions.

The main issue that arises with casual dating is the lack of communicating that goes on. A girl might take your ongoing interest as a sign that the relationship is getting more serious, where you don’t have any intention of ever being serious with her. Frequently you will not be on the same page as other people, which can put a halt to some of your relationships and to the fun you were having, but in the long run that’s the easiest thing to do.

It’s never going to be completely simple to be dating multiple people, but if you are honest about what you want and are fair about it, no one can turn around and say that you were a bad guy. Saying no isn’t wrong, saying yes when you don’t mean it on the hand, is wrong.

Pay attention if your feelings change.

Of course we’re all human here, and sometimes your feelings for people change throughout the process of casually dating. If you suddenly realize that you really don’t like someone or that something is off, let them go before things get weird. On the other hand if you realize that you’re starting to develop deeper feelings for someone, you better figure out what that means for her and for the other people that you’re seeing.

If you change your mind and feel ready to get more serious with one person, than being tactful as you get of the others is key. Remember that you initially told them that you weren’t looking for anything serious and then low and behold you caught some serious feelings…with someone who wasn’t them. They might feel a little rejected because they are, so ne nice.

Even more complicated is if you start to feel serious feelings for someone, but still don’t want a serious relationship. Because then you’re caught between wanting to keep them but not keep them too close. Ugh. I’ve been the girl in that situation many times, it really blows. As always the best thing that you can do is be honest with both her and yourself. If you’re scared just tell her you’re scared and see what you can work out. But if you’re certain that the timing is off and you won’t be able to commit the way that she wants even though you love the girl, you better set her free so she has the chance to find someone else who can.

Don’t talk about the other people you’re dating.

Just because your relationships are casual that doesn’t mean that your ladies are your homies. Don’t try to bro up to a woman that you’re sleeping with and tell her a story about the last girl you banged. Not happening playa. I don’t care how cool she is, or whatever she says that you makes you think she doesn’t care. Chillest girl in the world will be set off by you disrespecting her, and showing that (or pretending like) she’s easily replaceable is not going to come off as respectful.

It doesn’t matter how many women you can bed, the fact that any of them are literally willing to let you in means that you owe them some respect. When we shut it down for good we shut it down. When you want to keep things steady, avoid rocking the boat. Even if she’s totally cool with being casual she still want to feel like you like her.

Don’t date friends.

Your fun won’t last long if you’re dating women who are friends with each other. It’s not worth the risk unless you’re serious about pursuing someone in a serious way, which is a totally different story. If you’re not serious you don’t need to test out everyone in the group. It is inevitable that they are going to know about it, which usually will just cause more problems for you because it might cause problems with them.

Take it to Tinder and spread out a bit or something, there are plenty of single people out there, more than enough to create some distance between them. Listen these dating apps make it easy, most of them already tell you what friends you have in common. Checking out her Instagram will do the same, at the top of her profile it will show your mutual connections. You’re bound to know some of the same people, but like going after your ex’s best friend probably isn’t a great idea.

Don’t take them all to the same bar for date night.

You also don’t want to hang out at the same place all the time when you’re taking your ladies out to eat or whatever. If you introduce them all to the same awesome spot, then some of them might want to return with their friends as well. And when they do, they’re going to walk in and see you at the exact same spot at the bar but with another woman. There’s really no way to make that not awkward for someone.

Girls don’t want to have small talk with another girl who’s doing the same due at the same time. Girls don’t even like to have small talk with girls who used to do the same guy six years ago. You’ll have to introduce them without explaining how you know everyone, and the friends the girl walked in with will be sending you dagger eyes all the while. If you’re lucky the bartender will watch this go down and bring you a drink on the house to help smooth things out. But some damage will be done.

Don’t let them leave their crap at your house.

You can’t be dating multiple people and put women in the position to come across another woman’s bra on your bathroom floor. Don’t do it. That’s just asking for trouble. If you’re casually dating no one needs to leave a toothbrush or their makeup remover. And please do not leave your used condoms or condom wrappers in the trashcan where they are visible for the next person to see. You can’t unsee that, and it’s not an image that any woman wants in her head whether or not she knows that you’re seeing someone else. Shudder. Use the condoms by all means, but then take out the trash.