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How To Date Multiple Guys Without Being Shady (13 Honest Ways)

Dating multiple guys is a grey area in dating. Some men will instantly think that you’re a player. Others might label you some not so nice names if they assume that you’re sleeping with all of them. 

However, don’t let those people get to you. There is nothing wrong with dating more than one person at a time. In fact, there are quite a few great reasons that you should be dating multiple guys at any given time. 

How To Date Multiple Guys Without Being Shady

I’ve spent quite a bit of time in the dating world. There were long periods of being single. I had a few long term relationships. When I was “single” I was usually talking to at least one guy. There were quite a few times that I was talking to multiple guys at a time. It was fun. 

Dating several different men was great when I was younger because it gave me the opportunity to enjoy new experiences, and to find out what I was really looking for in a relationship. Along the way, I made sure that I didn’t come off as shady to the guys I was talking to with these tips. 

1. Honesty should always come first when talking to more than one guy

How to date multiple guys without being shady means trusting each other. If he asks if you’re talking to other men, tell him the truth. Let him know whether it’s because you’re just playing the field, dating guys to feel out who you would work out best with, etc. If he asks if you’re sleeping with multiple guys, you need to be honest about that too. 

I have a rule that I won’t sleep with a guy within three weeks of sleeping with a different one. I’m pretty honest with men about that too. Honesty lets guys know that nothing shady is going on. 

2. Practice safe sex when sleeping with more than one person

If you’re dating multiple people, and just so happen to also be sleeping with more than one person, don’t do it without using a condom. You don’t want to be on the Maury show if you wind up pregnant

You also don’t want to be phoning multiple guys because you don’t know who you got Chlamydia from. I’m all about sexual freedom, but it should also be fun. Not being safe can definitely take the fun out of things in the long run. 

3. Assume they are dating multiple people too

Assume they are dating multiple people too

If you’re dating multiple guys, you can’t exactly get mad if they are dating multiple people too. In fact, you should assume that they are. Assume they are sleeping with multiple other people in addition to you. It’s just part of keeping things casual. 

4. Don’t kiss and tell

Even if the entire friend group is sharing at this point, no one wants to hear about it. Guys don’t want to be reminded that you’re seeing other guys. It can hurt their ego. Likewise, girls don’t want to acknowledge that a guy they are talking to is talking to other girls. 

As an unspoken rule, keep your date stories for your closest friends when you choose to date multiple guys at the same time. 

5. Don’t feel guilty! There’s no shame in dating a few guys at once

One of the key things to keep in mind when learning how to date multiple guys without being shady is not to feel guilty. If you’re not doing anything shady, you really have nothing to feel guilty about. However, when you feel guilty, even if you’ve done nothing wrong, you give off guilty vibes. It can make you appear shady even though you aren’t acting that way. 

6. Schedule dates on separate days to avoid overbooking

It can be tempting to enjoy free breakfast, lunch, and dinner when you’ve got enough guys in the rotation. Let’s face it, if you’re dating multiple guys, it can be tempting. However, there are a few problems with this. 

First, it looks shady. Using men for a free meal, no matter how genius the idea is, is still a little bit shady. Second, if one overlaps then you’re late to the next or have to cancel. It’s just stressful, and this is supposed to be fun. 

7. Make sure that you know what you want when dating several guys

Do you want a serious relationship? Then that’s what you need to go after. If you want to date someone, or several guys, casually because you’re not ready for a serious date, that’s fine. 

However, you need to take a good look inside yourself before you date multiple men to make sure that you’re doing what you want. If not, you’ll wind up attached to all of those guys without being committed to any of them. Ultimately, these leads to multiple men wondering what happened, and you being heartbroken. 

8. Make sure that they want the same thing if you plan on going out with other people

Make sure that they want the same thing if you plan on going out with other people

Being honest is always a must, but you need to make sure that they feel the same way. You don’t want someone to show up at your Thanksgiving dinner because they think that you are the one for them when you were only casually dating them. The next worse thing is when one of the people you’re dating gets mad you’re dating someone else, or asks the “what are we” question. 

This makes it abundantly clear that you were not honest enough, or they didn’t get the message. 

If you’re seeing other people, make sure that they are well aware of the other people in your dating life. Once you do this, some people will hit the road because they do not want to share. That’s fine. There are plenty of people that will stay because they are enjoying what they have going on in their own dating life. This guarantees there will never be a question about what either of you is to each other too. 

9. Don’t act like his girlfriend if you’re seeing someone other than him

If you’re casually dating multiple people, don’t act like his girlfriend. This leads one of the guys to believe that you have feelings for him, even when you don’t. You need to be casual about this or don’t do it. Once you start to go into girlfriend territory, it seems like you were being dishonest about what you really wanted. 

10. Don’t play games with their emotions if you’re casually seeing multiple people

This is another one of the biggest things you need to know about how to date multiple guys without being shady. Know why you’re doing it. Be honest and upfront without being hurtful. 

Don’t date multiple men and tell them all the same thing or try to make them fall in love with you. Never play with their feelings, either. None of that is okay. Emotions are not something to be played with. 

11. Don’t go overboard and date too many people

If you’re wondering how to date multiple guys without being shady, remember this one. Don’t ever add too many people to your dating life. It can boost your ego that a hundred guys want to date you, but that is way too many people. Instead, know what you can handle. Start with two or three. 

If it gets to the point that you’re mixing them up, it looks bad. If you have a horrible memory, this dating style might not be for you. 

12. Don’t lie when they ask you something

This almost contradicts not telling the guys about the other guys, but not if you think about it. You don’t want to specifically name people. 

For example, if one guy asks if you’ve slept with anyone else recently, you need to be honest about whether you have. That does not mean that you need to name every guy you’ve been on a date with. If you can’t date multiple guys without being honest, you shouldn’t be doing it. 

13. You might catch feelings even if you’re going around with two people

Dating casually is supposed to mean that there are no feelings involved. No matter how hard you try, sometimes it happens. 

If you follow all the rules on how to date multiple guys without being shady, are not emotionally available, and are seeing at least two men, you can still fall for one of them. Accept it. When it happens, just decide if that’s something you would like to pursue or not. 


Is it OK to date multiple guys at the same time?

Yes, but it’s important to learn how to date multiple guys without being shady. Be honest if you’re seeing other people. Don’t lie if you’re sleeping with someone else, either. Make sure that you can date multiple guys without being shady, using them, or playing games, too. 

How do you date multiple men?

If you’re wondering how to date multiple guys without being shady, remember that it all starts with you. Be honest with all of them. If they choose to date multiple people, don’t get jealous. Don’t overbook. Don’t talk about one guy with another one. Always practice safe sex. 

What is the 3 date rule?

The three-date rule states that you two go without having sex with each other until the third date. On the third date, it is generally acceptable to have sex with someone without appearing too loose to be in a relationship with. 

How do you tell if a guy wants a relationship or just a hookup?

When he just wants a hookup, he won’t care if you date multiple guys. In fact, he won’t bat an eye when you mention that you date multiple guys. He also won’t show any interest in your personality. A guy that just wants a hookup will only compliment you on your looks. 

How many dates until you are in a relationship?

Most people know whether they want to exclusively date someone after the third date. This does vary. Some will not know until the fifth or sixth date, and some will know after the first date. How much communication there is between dates is a good indicator as to as soon you will be in a relationship. 

In Conclusion

Have you ever tried to date multiple guys without being shady? What are some general guidelines that you would encourage other women to follow?


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