How to Date Multiple Women at Once

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Not everyone is ready to settle down with one partner. Some people choose to have multiple relationships at once for their whole lives. If you're thinking of dating multiple women at once, it can be done. However, you'll need to behave honestly and ethically to make it work.

Part 1
Part 1 of 3:

Honest Communication

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  1. Never lie simply to keep a woman interested—it's best to be upfront if you're planning to continue seeing other people. [1] If you’re only looking for casual hookups, let her know. You may be surprised to find that she’s also interested in that.
    • You can ask her what she’s looking for before you disclose your own interests. You can say, “So we’ve never talked about what we're each looking for. I’m curious what you think about that.”
    • Choose an opportune moment and keep it casual. If the subject of past relationships or future plans comes up, you can say something like, “Since then I haven’t been ready for a girlfriend” or, “I have a hard time imagining being ready to settle down any time soon.”
    • Reader Poll: We asked 564 wikiHow readers about what they wanted from their romantic life, and only 8% of people said they enjoyed periods of casual dating without building any lasting connections. [Take Poll] So if someone you're seeing isn't into the casual dating scene, remember to respect that. And instead, go search for someone who has the same interests as you!
  2. It’s much easier to date multiple people if you feel casually about them. Once deeper feelings get involved, people may feel jealous or require more emotional support. [2]
    • Eventually, you may develop strong feelings for one or more women. If this happens, you’ll need to be honest with yourself and the people you’re dating.
    • Casual doesn’t mean callous. You should always treat the women you’re dating with respect and consideration, no matter how casual the relationship.
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  3. Sometimes, the way that you present something can have a big influence on how it’s received. If you appear to be direct and honest, women are more likely to be open to a non-exclusive relationship. [3]
    • Respond to texts or calls relatively quickly. If she senses that you’re too busy or disinterested to be in touch, she may feel disrespected. It also may seem like a sign that you’re not being forthright.
    • Don’t share unnecessary information. For example, if she asks if you’re free on Friday, you can say that you “have plans” rather than saying, “I have a date with someone else.”
    • If she presses you to find out whom you have plans with, or what you’re doing, you should be honest. But don’t give more information than she specifically asks for.
    • If you're sleeping with more than one woman, be honest and disclose that to each person. [4] That way, they can make an informed decision about whether to continue sleeping with you, or the type of safer sex practices they'd prefer knowing they're not your only partner.If you can’t agree on a set of rules, the relationship may not be viable.
  4. This goes for the women you’re dating as well as the other people in your life. Your family or coworkers may not understand your need to date multiple women. Never lie about your situation, but keep the details to yourself unless pressed. [5]
    • Use discretion when talking about your love life. You may want to omit the women’s names from stories if you’re talking to someone who likes to gossip.
    • Don’t share your feelings about one woman with another. Women don’t want to hear that you’re gaga over someone else. They also may think you’re inconsiderate if you tell them what you dislike about other women you’re dating. If you need to vent, talk to a friend.
    • If one woman presses you for information that you don't want to share, you can say something like, "I'm sorry, but I don't feel comfortable discussing that with you," or, "Do you think it's really important that we talk about that right now? Because I'd rather not." If she does think it's important, you can decide whether or not you want to honor that.
  5. You’ll need to have this discussion with each of the women you’re seeing. You are not making a monogamous commitment to any of them, but you can still make other commitments. These rules will help avoid misunderstandings in the future. If you can’t agree on a set of rules, the relationship may not be viable.
    • Rules may include things like who you may or may not date. For example, it may be off limits to date a friend of the woman you’re seeing.
    • A woman might say it’s okay for you to date other women, but not to have sex with them.
    • You don’t have to agree to the same behaviors. For example, it may be fine with her if you date her friends, but you wouldn’t want her to do the same.
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Part 2
Part 2 of 3:

Evaluating Your Needs

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  1. There are many reasons you might be dating more than one woman. You may have just gotten out of a long, difficult relationship, or you may be someone who is naturally polyamorous. [6]
    • It’s good to know whether you imagine dating multiple women as a long term plan or as something that simply suits you right now.
    • It’s okay not to know what you want in the long term. But be ready to be honest about that with the women you’re dating.
  2. If you’re looking for long-term polyamory, look for other women who are also interested in that. If you are simply looking for hookups, try to find women who want that as well.
    • Most online dating apps allow you to state what you’re looking for. If you’re looking for hookups, don’t get involved with women who are looking for marriage.
    • If you’re looking for hookups, don’t plan elaborate getaways or very romantic dates with a woman, or she may get the wrong idea.
  3. If you’ve never dated multiple women before, you need to spend some time getting used to balancing more than one relationship. Don’t try to go from being monogamous to dating five women at once. [7]
    • You can read books or blogs about polyamory and other lifestyles that accommodate dating multiple women.
  4. Over time, and depending on who you meet, your interests may change. If they do, be honest with yourself about your feelings. Don’t try to deny them, or you and others are likely to get hurt. [8]
    • If you begin to fall in love with one person, or multiple people, you may need to have a serious conversation about that with all of the people you’re dating.
    • Having strong feelings for someone doesn’t have to mean you stop dating the others, but it may mean that the relationships change in some way.
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Part 3
Part 3 of 3:

Boundaries and Commitments

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  1. When you’re with one woman, dedicate all of your focus and energy to her. If she perceives you as a good boyfriend (or at least boyfriend material) she may forget while you’re together that there are other women in your life.
    • While you’re together, don’t discuss the other people you’re dating unless it’s absolutely necessary.
    • Don’t get sucked into your phone or social media while you’re on a date. Keep your focus on the person you’re with. The other women you’re seeing can wait.
  2. Remember that non-exclusivity often works both ways. You should always assume that a woman you’re seeing is seeing other people as well.
    • Eventually, you will need to have a very explicit conversation about exclusivity. Sometimes that conversation happens very quickly, sometimes it takes months.
    • If you get jealous easily, it may be difficult for you to handle the knowledge that someone you like is seeing other people.
  3. Juggling multiple relationships can mean tricky scheduling. Keep a private calendar where you can keep track of the dates you have planned. This way, you can avoid double booking yourself. [9]
  4. This can be hard and can take some finesse. Try to avoid commenting or liking every photo or post by the women you’re dating. While you don’t need to hide the fact that you’re seeing multiple people, you don’t want to feed anyone’s insecurities or jealousies. [10]
    • Don’t post photos of yourself with the multiple women you’re dating.
    • If women tag you in photos with them, you can remove the tag and then talk to them about it. You can say something like, “I’m not really comfortable being tagged in photos right now. I’m seeing a few different people, and it feels awkward to post photos of myself with one person.”
  5. Jealousy can affect non-exclusive relationships and exclusive relationships alike. However, by dating more women, you're creating more opportunities for jealousy. The best way to deal with jealousy is to be honest without going overboard. [11]
    • If one of the women you're dating expresses jealousy, say what you can to reassure her, but don't lie. For example, if it's true, you could say, "It's true that I have a strong connection with that other woman, but that doesn't diminish how much I enjoy spending time with you."
    • You can also use this as a chance to be honest if the jealousy is well-founded. You could say something like, "I guess I have been spending more time with her. I think that relationship might get more serious at some point, but I am still excited about seeing you right now." This can help a woman know where she stands in your eyes, but may cause some women to end or slow down the relationship.
    • If you find yourself being jealous because one of the women is seeing someone else, let her know. Don't make a big deal out of it or lead with anger. Simply say something like, "To be honest, I've noticed that I'm kind of jealous of the other person you're seeing. I think I'd like to have more of your time and attention."
    • No matter who is feeling jealous, being honest about it is a great way to start a conversation. It can help you both understand more about what you want and what helps you feel secure.
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Expert Q&A

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  • Question
    How can I handle dating multiple women at once?
    Louie Felix
    Dating Coach & Matchmaker
    Louie Felix is a Dating Coach and Matchmaker, and the founder and CEO of Matchmaking VIP, a company which provides concierge-level matchmaking services to clients around the world. He is also the COO of Agape Matchmaking based in New York City. With almost 16 years of professional matchmaking and dating coaching experience, Louie has served as CEO for the United States' two largest matchmaking companies serving over 50,000 clients. He has been featured as an expert matchmaker for shows on E! Entertainment Television, WeTV and the CW. He was also recently acknowledged as a top 5 worldwide matchmaker by both the International Dating Conference and the Matchmakers Alliance. Louie was also selected as one of America's top 10 Relationship Experts for the Great Love Debate National Tour.
    Louie Felix
    Dating Coach & Matchmaker
    Expert Answer
    A: It's very important to be upfront about it. Also, I don't think it's acceptable to sleep with multiple people at the same time, but if you are, you should be very open and honest about it.
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      Warnings

      • The more women you have sex with, the greater your chance of contracting and spreading sexually transmitted infections. Always practice safer sex by using condoms.
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      • More relationships can also lead to more heartbreak. Don’t assume that just because you’re seeing multiple women you won’t get hurt.
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      References

      1. ↑ Louie Felix. Dating Coach & Matchmaker. Expert Interview. 5 May 2020.
      2. ↑ http://www.gq.com/story/sex-column-how-to-date-multiple-women
      3. ↑ http://www.gq.com/story/sex-column-how-to-date-multiple-women
      4. ↑ Louie Felix. Dating Coach & Matchmaker. Expert Interview. 5 May 2020.
      5. ↑ https://www.glamour.com/story/how-to-correctly-date-multiple
      6. ↑ http://www.datingadviceguy.com/the-numbers-game/
      7. ↑ http://stylecaster.com/benefits-dating-multiple-people-at-once/
      8. ↑ http://stylecaster.com/benefits-dating-multiple-people-at-once/
      9. ↑ http://www.refinery29.com/2014/02/62119/dating-multiple-people
      1. ↑ http://www.gq.com/story/sex-column-how-to-date-multiple-women
      2. ↑ http://www.gq.com/story/sex-column-how-to-date-multiple-women
      3. ↑ Louie Felix. Dating Coach & Matchmaker. Expert Interview. 5 May 2020.

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