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

  • Sorry I didn’t understand. Does that mean its is ok to have a boyfriend and see other guys at the same time? English is not my first language so I don’t know if you date someone, it means he is your boyfriend? Or before you call someone a boyfriend it is called dating? Could you please explain for me? Thanks :)

  • Sorry I didn’t understand. Is having a boyfriend equal to dating? English is my second language, so I am not sure about that…
    If they are the same, does it mean that these ladies have a boyfriend and see other guys at the same time???

  • Matt, I think Taylor would thank you for this article, clearing things up and all.

    Of course, I don’t stop being friends with other people just because I’m spending more time with someone. How is that morally loose right? But there’s where it all gets confusing. Where I am, we have to be careful to establish that we’re “not going a date” when we meet someone alone, because going on a date/going out alone with the opposite sex automatically makes it a relationship to many people here. Including my parents. Worse if you are to listen to my neighbours’ gossips…

    I guess the “line” drawn between dating and being in a boy/girlfriend relationship is not an absolute. That, or people are just confused about what they believe in.

  • Hi Matthew!

    I’ve only recently come across your book, I was a bit sceptical about the title at first but a sneak peak led me to read the whole thing and it’s great! A totally different perspective and really useful, so much in fact I’ve even shared it on my blog!

    I love Taylor Swift actually, her songs are too catchy! From what I see I don’t think she dates multiple men at a time but just one after the other and this relationship hopping can be really hurtful especially if, as she alludes to in her songs, she’s always falling ‘in love’. ‘In love’ is a different level to just liking. Some people get crushes easily and others like myself don’t, so, assuming Taylor is the former, I can see how this can be quite frustrating for women seeing it.

    I don’t really have a problem with it but I do get a little worried however that, whereas it was real when she was younger, she may now only be using the guys/the relationships as a muse for her songs, but we as we don’t know her personally we shouldn’t judge.

    I think a thing to determine is what the term ‘dating’ means for you. I used to think that once you started dating someone that was it – you focus on them to the exclusion of all men and eventually they’d become your boyfriend. Once I had a crush I would even stop thinking of other men because I wanted my crush to know I was totally single and available but my view has changed and I now see ‘dating’ as an opportunity just to get to know more about a guy. You can date someone once or multiple times without it becoming serious and if this is the case why can’t you date multiple men at one time? Like making friends…

    As someone commented earlier, if you lay your cards on the table early in the dating process then you have nothing to worry about. I personally, would keep it meeting up only and no sex during that time. If I really like someone that strongly though and I think it can really go somewhere (i.e I’m falling in love with them) then I stop seeing others and start a serious relationship i.e. they become my ‘boyfriend’.

    I’ve tried both and I think this works for me. Each to their own though. Taylor is probably looking for Mr Right just as we all are so maybe Matthew, you could send her your book!

  • Matthew,

    You have rightly pointed out that it is indeed a challenge for us women keeping options open once we’ve set our eyes on someone. It might just be the way we are wired as men usually don’t have this problem. I’ve always admired how some men can have multiple genuine relations / relationships with different women. I didn’t think it’s inappropriate, I envied them because they had a richer life than I had. I’m 28 years old and I have finally learned how to do it and be happy (guilt free!)

  • Interesting, though when I was single I never had a problem with this, I dated sever guys at one time and had a blast doing it, discovering what I want and DON’t want. I think dating around (notice I didn’t say sleeping around) is a form of growth because it teaches you not to settle. I didn’t settle down with one guy until I was sure he was THE ONE. He matched most of the checks on my list.
    I have far too many friends who have settled for the guy who was good for now not the one they should be with.

  • Apparently a few decades ago dating several men at once was the normal way to do things. But of course if you started to get serious about one you would stop seeing the others. If Taylor Swift is “getting serious” about one guy after another I can see how that would be irritating.

    I think dating several guys at once is a good option, because it takes the pressure off and gives you more time with different people so you can make a good decision. I’ve never had the opportunity, though. :-)

  • Hey Matt!
    Well, thi is what I do! I like dating different guys. There’s nothing wrong with that. It can help you identify your real needs, plus it boosts your self-confidence, right? The only drawback is the fact that when you finally make a decision and want to stay with only one of these guys, you should let the others know that you’re not interested anymore, which is kinda difficult to do. Be open-minded girls. Don’t let things happen for you! If you really wanna meet a great guy, you have to go out and find him!! ;)

  • It depends on what you mean by dating multiple people. If you mean hanging out and having fun with, until you commit to one person who also commits to you, it’s great. But if dating lots of people means sleeping with all of them.. :( No.

  • I think it’s important for women in their early 20s to “circular date.” It is important from the standpoint that if you don’t meet and date a lot of people, you won’t have a very good idea of what you really need or want in a relationship. Dr. Henry Cloud talks about that in “How to Get a Date Worth Keeping” – that you should date with the objective of getting to know people from different walks of life, who might or might not be your type, so you get a better sense of what kind of person you’re looking for. After age 30 (if you didn’t get married at 18 and divorced at 29, that is – if you were single in your 20s and dated a lot) you should have a better idea of what you need. Adults over 30 (and moreso, over 40) have a pretty good idea of what they want, and don’t need to waste a lot of time looking around, figuring things out. For the 35-ish set, it’ important to get really targeted in your dating, and not accept anyone and everyone as a potential date. Amy Webb’s book “Data: A Love Story” is a good example of how successful this approach can be, once you have a really clear picture of all your “data points” – i.e. qualities you must have in a partner.

  • I see nothing wrong with dating different guys at the same time. If we haven’t established we are dating exclusively, it shouldn’t be a big deal. I’ve let great men get away because I was focused solely on one person that down the road wasn’t interested in any kind of commitment anyway. Don’t be foolish ladies!

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  • I don’t think it is…I was married to one man for a number of years and very devoted to him even to overlook his cheating ways a couple of times. This cheat time…He became verbally, sexually and monetarily abusive towards me for the 2 years before I threw him out and filed for divorce…only to discover that he was on his 3 round of cheating. I had no desire to go from one man to another and maybe a worse situation. Dating many different men has allowed me to develop the good qualities I want and also focus on red flag behaviors that I overlooked during my first marriage. Dating doesn’t have to involve sex…that’s your individual choice. But what is important is getting tip know one another on multiple levels.. Asking many questions along the way and getting truly in tune with what you want and how you want it in a new relationship.

  • No. From personal experience, I meet a guy I really liked but my date rejected him because papa said he was ugly. And my father encouraged me to date other men. When I ignored his advice, dad had my aunty invite me on a long vacation far away. After separating us, I returned home and now dad was able to talk me into seeing other guys. So I told my guy that papa said so. My boyfriend said he would wait for me. But when I returned to him after 6 montages of seeing other men, wI had poisoned the relationship. He was constantly angry now and often called me a slut when other men looked at me. Sad but I never got married. Why? Dad kept talking me out of relationships. And if that didn’t work, he drove them away with violent threats. Oh well. No grandkids for him. But ultimately, I was to blame.

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