Is It Wrong To Date Lots Of Different Men?

I don’t exactly have my pulse on pop stars and who they are dating but I have noticed that there seems to be a lot of vitriol directed at Taylor Swift and its not for whether or not she can hit all the noted. People, and more specifically women, seem to be very upset about the fact that she dates around a bit….ok, a lot. What’s confusing to me is that I hear a lot of women complain that when men date a lot they are considered studs and when women date a lot they are considered loose, so why all the hate directed at Taylor Swift?

At first I thought that it might be jealousy. She seems to have dated a lot of guys the most of my girl friends admit to having crushes on. Its understandable that you might want to put yourself in her shoes. And if she dated multiples of them it might even seem she was being a bit greedy. But, overwhelmingly, it seems its not about that but about the fact that she doesn’t take enough time in between relationships, or that she’s going through them to fast. Does the public only like Taylor Swift when she is heartbroken, alone and writing a song about it?

In my seminars I have come across the phenomena that when a girl likes a guy she immediately stops dating any one else. Again, this is when she just likes a guy. Not after the first time he shows interest, or after the first day. This starts when she sets her sights on him. My advise in this situation is always the same: when you are in the initial phases of liking or dating someone you should always keep the door open to meeting new people. That way just in case it doesn’t work out with the crush, you still have choices and options. It’s important to note that just because you have these options, it doesn’t mean you are exercising them, but simply having great people around you will have you putting less emphasis on the situation, which is really attractive to your crush.

The reaction I generally get from women is that they just can’t. Once they pick a guy no one else exists. I can’t imagine if I told them you should date multiple people or if I said its okay to date someone for a couple of months just to see how it goes and then have someone else lined up if it doesn’t.

Finding options and creating choice in your life is a challenge. A goal that can be accomplished with effort and some perseverance. Thinking that you don’t deserve to have them or that they are not appropriate for your life can be a major roadblock. Because even if you only want one special man, it usually takes a series of experiences with MEN (plural!) to get there.

I want to hear from you: is it wrong to date lots of different men? Is it okay to date different men at the same time? Sound off in the comments below.

Looking forward to hearing from you.

Matt x

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68 Replies to “Is It Wrong To Date Lots Of Different Men?”

  1. to me it is like being a player – that is what taylor displays to me a big player and then the fact when she is done dating a guy she literally destroys them in her songs filled with hate and anger – to me it seems as if she needs to grow up and stop blaming the men she dates and to turn the finger back at herself so she can fix what is wrong with herself rather than attacking the men. this and besides the fact that i just plain dislike her alot.

  2. its okay to date men.. ur rite.. we never know who is the best one.. so yes.. why not date more men? if we are still getting to know each other then yes… date and go out with lots of men..

  3. I think it’s good to keep your options open and date around. The thought of meeting a guy and focusing all of my attention on him right off the bat scares the hell out of me! I would feel stuck! I have a friend who always falls hard for a guy, ususally one she barely knows, and jumps right into a serious relationship. Then she seems to forget that there are other people on this planet and when they break up most of her friends have left and she is all alone.
    I think it’s okay to date different men at the same time but it’s not for me. I would be thinking of all the ways it could go wrong! What would a guy think if he found out you were seeing others at the same time? These are my thoughts, but I don’t have much experience to go on… :/

  4. Dating a lot of men is fine as long as you respect yourself and the person in front of you.
    There is nothing wrong with being a high value woman and being hopefull that every crush that we have might be the one; which is exactely what Taylor Swift is. She just falls for guys and genuinely believes it could lead to that fairytale we all long for.
    I see nothing wrong in that. :)

  5. Yes and no. I understand what you’re sayin’ and I agree with the whole have options. But sometimes it can backfire. If Dude #1 finds our you’re talking to 2 more dudes, he’s either gonna think you’re a slore or that you don’t take dating serious and you’re just out to “party”. And it seems now-a-days guys are expecting for a girl to jump in bed like right away. And what if all the dudes the girl’s seein’ is expecting that also? Could make her not wanna date guys at all and turn to girls instead. I don’t know haha. These are things I’ve went through or friends. I say it’s a gamble when coming to date in multiples. And I think Ms. Swift moves too fast and it ends up pushing the guy away.

  6. It’s not wrong at all. To me it looks like she gets easily infatuated and kinda makes her look inmature by how short those relationships seem to be and kinda intense at the same time. All in all, my perception is she gets totally invested into a new relationship from the minute she puts eyes on someone and even though the relationship ends pretty fast, she’s equally fast to move onto the next one with the same intensity and so on, it just doesn’t make too much sense to me.

    If I just like a guy I will date him and so on but I won’t be as into him as if I was madly in love, obviously, Taylor doesn’t seem to make much of a difference.

  7. Argh I would like to take your seminar! You coming to New York anytime soon? :D

    It’s always been very hard for me to date more than one guy at a time, and of course it’s not that I’m too simple so I can only concentrate on one guy at a time. I’m just not interested in anyone else at that time. Maybe that’s the wrong way to look at it, I don’t know.

    I’m actually not like that when I MEET someone for the first time. I can have a little crush and still be meeting new people etc. but if it goes into dating and I’m very excited…at THAT moment I’m not interested in meeting anyone else because the beginning is always the most exciting part and kind of a rush. Then if the dating doesn’t go well I move on and no problem….if the guy ends it I sometimes get disappointed, sure! But if it’s in the beginning stages and he’s honest about why he’s ending it I can move on.

    To be completely honest I come from a country where no one knows how to date so when I moved to New York I was like a teenager starting out in the dating world. I don’t even understand how people find each other back home…! But that takes too long to explain :)

    But I definitely don’t think it’s wrong to date more than one guy at a time! And if Taylor Swift is doing that and is happy while doing it I don’t see a reason to be bitching about that. And while we’re at it…no girl can say that if all THOSE guys would be throwing themselves at you….wouldn’t you go for it? ;)

  8. I don’t think it’s wrong to have dates with different guys and I don’t understand why so much hate.. dont be jealousy! any girl dreams to have a date with any of his handsome ex-boyfriends ..GOOD FOR HER!

  9. For the most part, there really exists this strong internal response when a woman starts to date a man she likes. Suddenly she doesn’t think about other guys and she stops dating other guys or looking for other options. The guy on the other hand usually does not do that. Particularly in the US, what I notice is that men have less and less of a desire to be with one woman. Whether they’re looking for the next best thing, or they have intimacy and commitment issues, or they don’t know what they want, or they have decided they are only into a polyamorous lifestyle now that it has become in style, it’s rare to come across a guy who is willing to treat a woman like she’s the only one. The times are showing us women that it’s emotionally safer to keep dating a variety of men and not allow ourselves to get all excited or have our hopes up about being exclusive with one guy who most likely does not feel the same. It’s healthy to date around. We learn about what we don’t want and what we do want. We learn more about ourselves and others, and we improve our communication skills in the process (hopefully). Sure, we have the added pressure from society that still says that women who date around are sluts while men who date around are studs. Dating doesn’t necessarily imply having sex. Regardless, we simply have to decide if we’re going to create our own reality or if we’re going to let the non-committal guy we like or society’s made up rules determine our reality. Regarding Ms. Swift, I say good on her for dating different men. She knows she’s a woman of high value and she’s not going to settle for the first guy who pays attention to her and certainly not the guy who is not paying enough attention to her, no matter how much she may like him. Perhaps if her lifestyle bothers some women it’s only because they know this truth that we are speaking of, and they hate it, yet they feel threatened by Ms. Swift’s ability to do what the guys are doing and date around until she finds the man and the commitment that she wants.

  10. I never have (and most likely never would) date several men at once. Reason being, I wouldn’t like it if a guy I’m into is dating several other women at once. It would devastate me as I could only be seen as “one of the options” or “the back-up plan”. Vice versa, you know? So to put it into context, I wouldn’t want to do the same to a man I’m seeing. He would think I’m either leading him on or using him as a “back-up plan”. Dating and relationships are all about impressions you make on someone, and I don’t want to appear as a player in any man’s eyes. I would rather make him feel important by dating him only – one man at a time. IF that don’t work out, take time off, learn from the mistakes, get back on my feet AND THEN find someone new. That would also mean you respect that person enough not to find a “replacement” as soon as things don’t work out or already have a “replacement” prepared beforehand.

  11. There’s nothing wrong with dating around. I don’t think that’s what bothers most women about Taylor. The thing that most of my girlfriends find frustrating is her dating many guys and nonetheless being portrayed as a sweet innocent girl. Simultaneoulsy, someone like Mylie Syrus who’s been committed to one guy for over three years is perceived as a ‘low value woman’, if I may use get-the-guy approved terminology )) So, it all depends on the perspective

  12. I’ve noticed that women can get a little hostile toward another woman who is dating multiple people. I’ve done both, the monogamous relationship and the I’m just dating approach and the trick is to be honest up front with the guys – “I’m really enjoying meeting up with you but want you to know from the start, I’m seeing other people right now and totally respect if that’s not your thing” (what goes unsaid but is generally understood is “I’m not going to change that right now so if it’s not your thing,that’s cool and we’re going back to the friend zone.” There’s usually a moment early on where this can be communicated without being abrupt or out of context, doesn’t need to be attached to your initial introduction, “Hi I’m Lauren and I’m dating around” – No. But other people aren’t flies on the wall in these clarifying conversations and have a tendency to see the worst, assume your sneaking around. They project feeling protective of the guys you might be tricking because they fear being tricked themselves. Bottom line, if you’re going to date multiple guys, be prepared for scrutiny and some chastising… If you conduct your business respectfully, the scorn isn’t really about you at all. Those people are basing their reaction on past experiences or personal fears.

    1. Hi Lauren,

      Very insightful. The respect issue was brought up earlier in a comment and I have to agree that it can make or break the dating multiple people situation. Thanks for sharing! x

  13. She is young. And therefore highly likely to change. A lot of people jump from one romance to the next. The difference is she is growing up in public. I think it is unfair to judge and condemn her. It is healthier physically and emotionally to take time out if a romance ends. But for some people the best way to get over a guy is to get under the next one. I don’t mean to be crude. My point is that her conduct may change over time as she matures in a tricky environment having learned from her experiences. The guidance and advice she needs could arise from these. Writing is a good outlet but again it is public and therefore less likely to be sympathised with. I say don’t hate because we all make mistakes and at some point we were also an example of getting it wrong.

  14. Dating decent multiple guys isn’t easy. Because there are more coals than pearls out there, but I’d highly recommend it.

    The best effect this has is it takes the pressure off the dates, you can sit back, relax and let the relaxed, sexy you shine through.

  15. This was really an eye opener for me. The part where you write about the women who stop dating when they have a crush, sounds exactly like me. I even stop looking at other guys when I have a crush on a guy.
    Maybe it’s biologically determined? And that’s why women don’t understand Tayler Swifts behavior, because it is more common with guys?
    Anyway, a late new year’s resolution for me will be: I will try to be more open for other guys and people in general, even when I have a crush. Thanks for the insight Matt!

  16. Hahaha I have to laugh because my coworkers know just how much I do not “appreciate” Taylor Swift. They have asked me why? My explanation is simple, it seems as though she’s dating to get another hit single. It seems like she’s a man hater in her songs sometimes, why do that?

    As for the other topic, yes I’m guilty of doing the same, for me it’s a fear of the guy that I like thinking he doesn’t have a chance if he sees/hears about me with someone else. I also know that I shouldn’t close the door to other opportunities it just takes a lot of work to get out of the “fantasy world” and come back to earth long enough to get my head back in the game.

  17. Nice topic Matthew!
    Some of my colleagues are astonished how many dates I always have and are not looking very nicely upon it either but tbh I don’t care and here’s why!

    I used to have the same problem.I would like one guy and suddenly what I call my ‘Men Radar’ would shut down.. I’d like to compare it with a horse who has those view blocker things on the side of their eyes, so they could only see in front and not on the sides because it can confuse them. It’ts the same.As soon as I started liking someone, immediately the radar shut down, eye-patces went on and all I saw was this one person even if it was just the dating phase. Thinking back it was obviously stupid as I took myself away from the market, set all my expectations on one person already without even knowing if he’s worthy or not and with one guy I actually never got to the wanted relationship but kind of was out of the market and hanging about for about 6 months!!! :D

    Now I’m smarter and even tho I have someone who I enjoy dating, I still try to keep my options open, I am not taken until the ‘girlfiend’ tag goes on.. but obviously all the dating that I do atm, I do whilst keeping in mind that I am a high value woman and I’ts nice to see who really makes an effort on the dates and compare, and at the same time not getting too fustrated if something goes worng. Its the same example as u made on ur ‘ Psychology of Entrepreneurship’ video- keep several plates moving at the same time:)))

    Love u Matthew:)

  18. In order to find that one special person it’s usually a good idea to date more then just one. I think we have forgotten that just because you go on a date doesn’t mean you are in a exclusive relationship. In this day we are too worried about being alone we forget to enjoy life and take things as they come. Trust me I know being single sometimes is hard but don’t let that determine your happiness.
    As for Taylor she is young and I just hope she isn’t one of those who has to be in a relationship especially when she’s gonna turn around and write a song about it. I just think she will look back one day and be so embarrassed that she let everyone know all her emotions. Going back to the whole fear of being alone I’ve had so many friends who suffered from that syndrome that in the end their love lives became a big mess usually ending in divorce. I guess my point is be patient and make wise choices and don’t be in such a hurry.

  19. One of my friends tweeted Maybe it’s time Taylor Swift wrote a song called “Maybe I am the problem” I know it’s mean but when you go through that many heart breaks it’s about time you stepped back and did some evaluating

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