How You Can Successfully Date More Than One Man at a Time


By: Krystle Crossman

Before you settle down with one person for the rest of your life you want to explore your options. This means dating a few people at a time casually to test the waters out. But how do you go about doing this? Do you talk to one person that you are dating about another person that you are also dating or do you keep them in the dark? How do you talk to one about the fact that you are more serious about another? How do you break your time up so that you have time for each equally but still have time for yourself as well?

First off, going on dates with multiple people is common. More common than you may think in fact. There are a lot of people that will go on a few dates with different people per week. Don’t put all your eggs in one basket. Assume that the people you are going on dates with are sleeping with other people, they will assume the same unless it is made clear that you aren’t, and you will be able to ease the tension caused by expectations.

Make sure that you don’t share too much with your date. If you want to be honest with them about not being too serious at the moment and seeing others, that is fine, just don’t go into heavy details. Need-to-know basis only is best.

People expect bad things to happen to them, especially when it comes to relationships. If you are adult enough and take care of things the right way, it won’t be so bad. For example, if one person texts you and asks if you are free Saturday night, instead of ignoring them because you already have a date, respond as soon as you can and politely decline, but offer up some other times that you are free. If you don’t feel like seeing them again, be honest, don’t just ignore them and leave them hanging.

Finally, don’t look at dating multiple people as “playing the field”. Look at it as getting out and enjoying your life while you are young and have the time. Just remember that while you are out with different people, make sure to practice safe s*x at all times and be responsible with what you do and where you go. Most importantly, have fun!



  1. I really find this article offensive. If someone would have told men how to date more than one woman at a time imagine the uproar they would receive.

    So the impression I am getting is that men are suppose to stand around and hold themselves while women are free to play men as if they are some type toy of something.

    How many men or women do you know who really put all their cards on the table when they are dealing with someone, not many.

    And further more how many people are willing to accept the truth that the person they are seeing is banging somebody else. Women have this tendency to try to play emotional games with men just to see how he is going to react instead of just being real and keeping their business to themselves.

    Mind you this is just a mans perspective on this issue.

    • I agree 100% with everything you stated. SMH. It would be all kinds of craziness goin on if a man wrote this non-sense, encouraging all this “testing the waters” crap.

  2. While I can understand the desire to “test the waters” so to speak, however I can guarantee, just like Maliki says, if this were written the other way around for men instead of women, there would be a lot of feedback from women about it. If it’s good for the goose, it’s good for the gander.

  3. I’m a single mother, I date different guys occasionally, but I’m not having sex with any of them! In my opinion, testing the waters does not have to mean sexually! I believe in being honest and telling someone that you are dating other people, but I’m not at all for sleeping around! I’m in school for nursing, and I know there is no such thing as safe sex! No sex is the only true safe sex! Monagomy is the next best thing! It doesn’t take but a few conversations with a person to find out if you are compatible or not, you don’t have to go out with them or have sex with them to figure that out, I would not encourage anyone to date in this manner!

    • Jah Larry Dread on

      “In my opinion, testing the waters does not have to mean sexually!” Ok in your opinion what does “testing the waters” mean?

  4. Charles Micheaux on

    I can’t wait to read the next “TRASH” article…

    “How to be a worhtless HOE!”

    SHAMEFUL & DISGUSTING writing here.

    Charles Micheaux

    • I wonder what advise this genius is gonna have when that female pops up pregnant from a sexual slip up. This exactly whats been going on and the result is baby mothers not wives with a baby. Sexual slip ups happen, condoms do break at times and they say contraceptives are less then 99% when it comes to protection… Now adults keeping it real will be honest about relationships, and that is SEX is a major part of it. And men add that in the equation of qualification. So while shes playing games, possibly holding out or sexing one over the other, what is the one being denied sex is gonna do? WAIT? This is not realistic and its a dangerous game. It does even work for most men so how can it possibly work for a woman when she functions mostly with emotions and will usually give in to or want to have sex also? This is a huge risk and she has so much to lose.. This is pure crap.

  5. Jah Larry Dread on

    Trust me on this women have stated being treated as equal…this is a lie. I have to agree with Christopher and Maliki. If, this were written the other way around for men instead of women there would be an uproar of negative comments. Question? Someone please define “Testing the Waters?”

  6. In my opinion I think “testing the waters” can mean having sex OR it can mean dating various people to see what they’re about.

    While i do think that just as some have disagreed with this post if it were written the other way around there would be some to also disagree. Either way I enjoyed the post. I think the best thing in dating is honesty and respect and that’s what I think is being said in this post.

    The key to dating multiple people, whether male or female, is honesty and not removing the option for the other person to choose. Women do appreciate honesty. If she’s not the only person you’re seeing don’t make her think she is and vice versa.

  7. I don’t see the problem with men or women dating multiple people….let’s keep in mind people that a DATE is where two people go to dinner and a movie or a museum or a picnic or an amusement park, talk, get to know each other. The problem is that FUCKING has become synonymous with dating, they’re not the same they are two different functions. Both people keep it real and say I’m just dating right now not looking for a relationship, and just enjoy each others company. No sucking no fucking, just have fun! Shit when I was 19 I went on a date with a dude to a pumpkin patch to pick out a pumpkin to carve for Halloween, afterwards we went to a cozy country buffet type place and had a good meal. Did we fuck, no. Went out on a couple of more dates then we moved on. It was fun.

  8. women need to explore their options men do it all the time maybe we won’t get hurt so much if we didn’t put all our trust into one man it wouldn’t hurt so bad if we dated at least 3 men at a time

  9. I don’t think anything was wrong with this article. It sounds about right. It’s ok to date other people when you’re not in a committed relationship but just because you go on dates and stuff doesn’t mean you have to give the cooch to everyone who takes you on a date.

  10. Pingback: Successfully Date Multiple People | Lady J's Voice

  11. What is up with this site? Why are they blocking out everything? Little things? M_e_s_s, c_r_a_p, s_e_x? These are common words and there not offensive. Why is it our sites have to have all of these difficulties with them and silly things added to them. They never operate smooth and free from bugs? SMH…

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