What’s Best Way to Let a Great Guy Know I’ve Chosen Someone Else?

What’s Best Way to Let a Great Guy Know I’ve Chosen Someone Else

First of all: your books and blogs are literally priceless. They have changed my life in a way I cannot even put into words.

I have a question that may seem a good problem to have but I want to do the right thing. I recently became single so I joined a dating site and found an amazing guy. He is insecure (anxious preoccupied) so things started a bit slowly. Just at the same time an old friend contacted me. He recently became single too and we reconnected. He is more secure so things went a bit faster with him. So I have been hanging out with both these men. I have a secure attachment style.

They are both literally awesome in their own way. I know I am well compatible with both and I am highly attracted to both. Both have done literally everything right and shown they care so much. They are both husband material and both have expressed the desire to get married and not have kids which is exactly what I want (I am mid-30s, never married and no kids). And both are asking me to be their girlfriend and be exclusive.

I told both that I would like some time to evaluate long term compatibility but I know I have to make a decision soon. I am not a cheater. My question is how do I word the inevitable rejection that one has to receive? I know honesty is the best approach to things but I don’t want to hurt either and I think saying I was hanging out with someone else will hurt a lot even if we were not in a committed relation yet.

I know neither was seeing anyone else because they told me (I always avoided saying if I was or was not seeing anyone else because I hate lying). They did not do a single thing wrong and I would totally date each of the two if it was not for the timing. So how do I let one go, in the most respectful way possible, once I make a decision? Thank you!


Dear Rose,

Yes, these are high-class problems, but they are problems nonetheless.

At this point in time, you’ve likely already made your decision (this blog has a 4-week turnaround time) and I trust that with your moral compass, you’ve acquitted yourself well and are now in a happy, healthy relationship with a new boyfriend.

But for all of the readers who have been confronted with a similar situation where you need to break it off with a perfectly nice guy who has done nothing wrong — the break-up speech itself is always a source of consternation.

I wrote about this recently, but it’s still worth revisiting.

First of all, if you’re breaking up with someone, you’re not doing anything wrong.

There is a huge difference between someone feeling hurt and you doing something hurtful. That distinction is important and a lot of people have a hard time differentiating between the two.

First of all, if you’re breaking up with someone, you’re not doing anything wrong.

No normal person ever wants to hurt someone; that doesn’t mean that millions of people aren’t hurt every day. That’s simply the consequence of different people having different opinions and different needs. It creates friction. How much friction depends on the people involved and their relative levels of confidence and communication. For example:

If my wife tells me she needs a night out alone without me or the kids, should I feel insulted? Someone thin-skinned might. But that wouldn’t mean she was insulting me. All it would mean is that she spends so much time being a wife and mother, she needs some space to reconnect with herself and her friends. Period.

Listen, I’ve made many people upset over the years both on and off this blog, and for the many thousands of interactions I’ve had, there are only a handful of times that I’ve actually tried to do something hurtful (out of pain or immaturity).

All the other times I’ve “hurt” someone has been because they didn’t want to hear my truth — or didn’t agree with it. That’s called collateral damage. I’m not intentionally inflicting pain on any woman who turns to me for advice, just because I challenged her original premise. Intention matters.

All you’re responsible for is speaking your truth as kindly as possible.

So when you tell a man that you like him but you don’t see yourself spending every day for the rest of your life together, he may perceive it as a slap in the face. But that’s on him.

All you’re responsible for is speaking your truth as kindly as possible: you like him, you appreciate him, you think he’s going to make another woman very happy one day, and he deserves someone who is all in on him.

Yes, he may be hurt, but at least you’re not doing anything hurtful.

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  1. 1

    OP, are you asking to try to avoid inflicting pain, or are you asking to try to leave a door open with the one you reject in case the one you choose doesn’t work out?   I’m not asking to try to advise you about how to do it.   I’m asking to point out the “paradox of choice” – that we can only be happy with something or someone if we aren’t always wondering what would have happened if we had chosen otherwise.   Best to make your choice, be polite and compassionate, and then don’t look back.

  2. 2

    Very well said Evan. My last serious relationship, I procrastinated to the point where he was wanting to move in. It was then I knew I had to speak up. I had outgrown the relationship and our goals were definitely not in alignment. I just didn’t want to hurt him, I delayed that inevitable conversation because I knew he would be crushed. For myself it was not a decision made lightly, however despite his protests it was for the best.

  3. 3

    Clear, yet polite and respectful is key. Quite often, the reasons we choose one person and not another is personal to ourselves, we know they will make another very happy. I hope you were able to make a decision! In case it’s still pending, just make sure you make the decision sooner rather than later, for the sake of everyone involved. And if at all possible, choose to give the bad news in a private place. The last time a guy told me it wasn’t going to work out, it was in the privacy of my own home. This meant not having to wade through a sea of people while walking home, and that made licking my wounds a lot easier! I was also on the other side a year earlier. I reheatsed what i wanted to say beforehand and went to his place. He was disappointed, but understanding and even uncorked a bottle of wine so that we could toast to the good times we had while dating! A very surprising yet classy reaction.

  4. 4

    I have to disagree with some of this: “you like him, you appreciate him, you think he’s going to make another woman very happy one day, and he deserves someone who is all in on him.”

    I think you tell him the first part about liking and appreciating him but that the two of you just aren’t a match.

    I think it is inappropriate to tell him that he’s going to make another woman happy and that he deserves someone who’s all in on him.   All that should matter is that he’s not right for you, period.   Leave other people out of it, even abstract people.   When you’re breaking up with him, he still feels as if you’re his gf and telling him to go find another woman  (in so many words) is really harsh.   I once had a gf tell me something along those lines and it felt like a punch in the gut.   I wanted her and she told me that I’m a great guy and I will find someone who feels the same way about me as I do about her.   It was crushing but she also did a sudden 180 on me. Hopefully Rose didn’t tell the recipient how happy and special he made her feel shortly before pulling the rug out.

    1. 4.1
      Evan Marc Katz

      Scott, if you’re the kind of guy who will take a compliment and twist it into an insult, no one can ever win with you. This level of sensitivity is counterproductive in the dating world. She’s giving you a nice kiss-off instead of a cold form letter. Why twist it into something “crushing”?

      1. 4.1.1

        Of course I’m going to be sensitive when the woman I care very deeply for tells me to go find another woman.   The suddenness of it didn’t help.   Two weeks prior, she acted like she couldn’t live without me and was talking like we would always be together.

        That doesn’t mean that I can’t take compliments.    Go ahead and compliment me.

      2. 4.1.2

        It’s not “crushing”, but isn’t a cliche now, and a bit condescending? The “you’re such a nice guy, you’ll make some lucky girl very happy” speech comes across as “you’re boring and unexciting, you’ll meet a similarly boring and unexciting woman eventually”. Its not really bad, just maybe its worth trying another line.

    2. 4.2
      Emily, the original

      Scott H,

      He is insecure (anxious preoccupied) so things started a bit slowly. Just at the same time an old friend contacted me. He recently became single too and we reconnected. He is more secure so things went a bit faster with him.

      A question about how the OP classifies her two boyfriends. One she says is anxious while the other is secure. Do you mind me asking what your take is on this? I know you have studied the book “Attached.” From my own personal experience, the opposite is true. An anxious person wants things to happen very quickly. 30 texts a day after 1 date. Pet names after 1 week. (This actually happened to me.) I would think things would happen at a comfortable pace with a secured attacher. He shows he likes you but isn’t coming on too strongly.


      1. 4.2.1

        Hi Emily- of course my ears perked up when she started talking attachment theory but she didn’t provide enough information as to why one started out slowly and the other quickly.   I didn’t see how the attachment talk was relevant to her situation since she states that they are neck and neck in the race- both are awesome, husband material, and doing everything right.   It is possible that the anxious one was too needy and she needed to slow him down somehow.   Take out the attachment-talk and nothing in the situation changes, unless she nods in favor of the secure one but she didn’t state anything to indicate that.

        I was watching Dr Phil today and he started talking about attachment theory with regard to children of the incompetent parent-guests of the day, not using the lingo but he described it exactly.   It was quite interesting.   I’m so glad that I understand the theory.   I just wish I knew it when my kids were born.

        1. Emily, the original


          Thanks for answering

      2. 4.2.2

        Emily, I am the original poster. Initially the anxious preoccupied guy was so insecure and fearful of rejection that he was waiting for me to call him and to tell him I was available to meet. He said he did not want to bother me and would say things like “let me know when and where you want to meet”. It took some time because I was not sure if I could tolerate so much insecurity so I was taking it slowly and he was too fearful to say anything even if later he said he wanted to see me very badly.
        Only later his clinginess started to show up in protest behaviors (complaining I was not chatty enough if I did not call him or text him etc). This is when I broke it off with him. And when I did he said “I will find someone that is as interested in me as I am in her, because you were not so much into me”.
        In other words initially he was passive but reasonable and super sweet. And I thought he just needed reassurance. But his anxiety was worse than I expected. After I sent my question to Evan he still remained passive but, especially after I was out of state for a week, started to protest that I did not give him enough attention by not initiating contacts enough (even though he rarely initiated it despite me telling him it was ok to call me).
        So it became clear I did not want to be with someone like that. He needed CONSTANT reassurance and I don’t want such a partner.

        1. Emily, the original


          So it became clear I did not want to be with someone like that. He needed CONSTANT reassurance and I don’t want such a partner.

          From your description, he sounds very demanding and manipulative. He’s way too much work.

  5. 5

    The key is to never say why, if they ask. That only opens the door for a negotiation.: “what if I [stop doing that thing]”? Sweet and short, like ripping a band aid off.

  6. 6

    I agree completely with ScottH – I don’t want to hear about others or have someone I care about allude to a future I might have with someone else when I’m being rejected. Also, frankly, I think a lot of men  are  sensitive. Telling a man he will make somebody else happy one day may be said sigh good intentions, but in my experience most men will  hear,  “You’re not good enough for me, but I’m sure you’ll be good enough for somebody else.”   When rejecting a man, the less that’s open to sensitive interpretation -warranted or not – the better!!

  7. 7

    *with* not “sigh”

  8. 8

    So I am the original poster. I knew the response would come after I had made my decision but wanted to send it to Evan anyway because I think it is a fairly common scenario.
    Here is what happened in the weeks and months after I sent this question: the anxious preoccupied guy was getting quite demanding and clingy. He wanted constant reassurance. I told him that he needed someone with more time than I could give him and that probably he needed someone less independent. He got upset but never contacted me again.
    I have since broken up with the other guy too who turned out not to be quite what I expected.
    But, to respond to Jeremy, I have NOT gotten back to the anxious preoccupied guy (my question was not to leave the door open… but to close it in a classy way) and I have just started seeing somebody new.
    Evan thank you so very much for answering my question. You are awesome!!

    1. 8.1

      Thanks for the clarification, Rose, and I wish you well with your new guy.


      One small point – the behavior you describe, where a guy leaves it up to you to decide where to go or when to meet, is not necessarily indicative of insecure attachment style.   It is simply a man who absorbed the messages that he has been taught his whole life (mostly by women) to be respectful of what a woman wants and not to impose his own desires on her.


      Frankly, I imagine the women who teach this to young men believe that boys will always be boys, and that they hope that their message will simply curb any masculine excess.   They don’t account for the boys who actually listen to what they are teaching and absorb it whole.   In my younger days I used to always discuss where to go with a girl rather than imposing a plan, and was SHOCKED to learn that this is not what most women want.


      It sounds to me (and I could be wrong), that this guy was more into you than you were into him.   And because he intuited that you weren’t into him he became insecure because he liked you.   Like a chicken and egg argument, which came first – the insecurity or the lack of attraction?   Hard to say.   But realize that just as if you were in a relationship with a man who seemed non-committal you would sense something wrong, many men feel the same way.   Hopefully he finds a woman who is more into him, and hopefully you find a man who elicits more desire for reciprocation in you.

      1. 8.1.1

        I dunno Jeremy, I think to me it sounds more like he has an insecure attachment style and probably out of the 5 love languages requires a lot of attention, words, etc. She sounds like she has a secure attachment style and doesn’t need to constantly be in touch with her partner to feel and demonstrate affection.

        I’m the kind of person who is just fine seeing her boyfriend once a week if that ends up happening  because I like my own space as well and seeing my friends and also am very secure in my romantic relationship. My boyfriend is similar. I wouldn’t say that means we love each other less than those people who need to see each other every day. I think as individuals we all have our own wants and needs and the key thing is to find the person who compliments that. Not that there is a general way of demonstrating affection we all must strive for.

        So in this situation I think she was really fond of him, there is no evidence in her original letter to suggest otherwise. In fact she was struggling with what to do dating both the guys because she liked them both a lot. But her different kind of attachment style probably made the insecure attachment guy really nervous. He probably therefore assumed (as you do now) that she liked him less than he liked him because to him (and you) constant contact is a sign of true affection. Even if it wasn’t the same for her.

        Ultimately I think she made the right choice, they simply were not compatible. But this idea  that there is only one right way to demonstrate love just isn’t true.

        1. jeremy

          You may be right, Callie.   We’re only going on her description, after all, and don’t have his side for balance.

          Where I may take issue with your comment is the “constant contact” description.   If this guy really did need constant contact, I’d certainly agree about the insecurity. But the OP describes a situation where she went away for a week and told this guy that HE could contact her, and he complained that she didn’t contact him.   Did she, or did she just wait for him to call?   If she tried to call him and he didn’t reciprocate, I’d agree with you.   If she expected him to do all of the initiating and sat back on her laurels waiting for him to “man up”, I’d just say that she wasn’t into him.

        2. Callie

          Also I want to add I think it’s a little dangerous to excuse his poor behaviour as that he was just more into her than she was into him. His behaviour was controlling and inappropriate (regardless of possibly the good intentions behind it), and she was right to end it. Something that a lot of women don’t do. A lot of women, despite such red flags, give guys big chances basically for the exact excuse you offered: “Oh he just really likes me.” (not sure how into musicals you are but Nancy in OLIVER! has entire song about “As long as he needs me” which basically excuses her boyfriend’s beating her and being generally terrible – it’s THAT common). And they end up in bad relationships because of it. I applaud Rose for actually knowing what she wanted, seeing the red flags, and doing what she needed to do for herself.

          (all this with the caveat that I don’t have any evidence this guy was an abuser, but his behaviour nonetheless was not appropriate)

          (I also want to point out that while I generally like your comments Jeremy, I do often find you give much more benefit of the doubt to male writers as opposed to female. Notice how here your first assumption about the LW was that she was interested in keeping her options open, and THAT’s what she was looking for from Evan, even though she was very specific about what she was asking in her initial letter: “So how do I let one go, in the most respectful way possible, once I make a decision?”   Yet at the same time see how easy it is for you to excuse away the insecure man’s behaviour as just him liking her too much, and not that he was being inappropriate)

        3. jeremy

          Callie, if their genders were reversed I’d have asked the same questions – both of the motivations for letter-writing and for the view that one was insecure due to wanting the other to reciprocate.   Now as to your suggestion that the guy’s behavior was somehow controlling (which I see no evidence of, but who knows)….I’m assuming you’d think the same if the genders were reversed, no?

        4. Adrian

          Hi Callie,

          You stated, “So in this situation I think she was really fond of him

          I think this happens more than we (on this blog) acknowledge.

          I am not bashing men nor am I trying to take sides in the ever on going men vs women debates on this blog.


          I believe that what happens a lot is that a woman does like a man but –for whatever reason– he is not picking up on it and therefore he ruins it by acting or saying things that cause her to lose the attraction.

          But since he never saw the attraction in the first place he gets bitter and angry saying that she only said yes to his dates because she wanted free dinners or saying that she was just using him until a man she really wanted came along.

          Again I am not saying that this does not happen; I am just saying that I agree with your point.

          Rose clearly stated to us that she found guy #1 attractive but he just could not see it himself and therefore did things to cause her attraction for him to disappear.

          -I do want to take a moment to acknowledge Jeremy’s point. Women should also do things to assure that the many knows she is attracted to him.

          Read any book on body language and it tells you that women are subtle and love soft little things while men love hard big things.

          Basically a woman can’t be subtle in her affection for a guy because he will most likely not notice it.-

          I am sure that many potential great relationships never happened because of this type of misunderstanding. Now I understand why in Evan’s early days of teaching when he taught men and women that he always told men that a clear sign that she liked you was when she said yes.

          I also now understand why so many men in the comments fought him on that.

      2. 8.1.2
        Emily, the original


        Like a chicken and egg argument, which came first — the insecurity or the lack of attraction?

        She probably was attracted to him in the beginning but his behavior turned her off.   Initially the anxious preoccupied guy was so insecure and fearful of rejection that he was waiting for me to call him and to tell him I was available to meet.  That indecisiveness will kill it for a lot of women. Complaining I was not chatty enough if I did not call him or text him etc If he wanted to talk to her, why didn’t he pick up the phone? He’s playing passive-aggressive games. Yuck.


        1. Rose

          I made a lot of first moves with the clingy guys. I said for instance the very first few days “we should talk over the phone” and he said “yes, I was waiting until you suggested that”. He would ask to get together but always leave it at me to plan things. I am partly ok with this again because I can accept some level of insecurity and especially because sometimes people do grow more secure and in that case you have a great, affectionate partner. But again this letter was never about him. It is about the many cases when you are starting to hang out with two people, and like them both and you then have to let go of one.

        2. Emily, the original

          Hi Rose,

          But again this letter was never about him. It is about the many cases when you are starting to hang out with two people, and like them both and you then have to let go of one.

          Thanks for answering. I guess, just on a personal level, there would never have been a question as to who to choose. The anxious one would have never been on the playing field. I don’t think I would have even made it to the first date with him. Too much walking on egg shells to make sure he’s ok. The idea of attachment theory has been discussed in many different posts on this blog, so I think people were curious as to why you considered the one anxious.


    2. 8.2

      Hi Rose,

      Thanks for updating us. It’s rare that we get this with the questions.

      1). If I may ask, if the 1st guy didn’t act so clingy then would you have allowed the second guy to enter the equation?

      Or taking the specific 1st guy out of the equation, if you would have met a great guy would you have still dated around and keep your options open?

      2). How long did you date these two guys before you decided to try to choose just one?

      I ask because there has been much debate on here as to how long a person should date around before committing to one person; too soon and you come off as clingy, too long and you come off as a player or not serious about the other person.

      3). You mentioned that he wanted more of your time. How much time were you giving him on the phone or meeting him? How long did you know him at the time that he wanted more of you?

      Again there is a division on this as well. Some posters feel that once a week is more than enough phone and face to face time and some feel that it is not enough. Personally I think it all depends on how much the woman is attracted to the man.

      4). Since neither guy turned out to be great catches (for you), how long did you know them at the time of writing the letter?

      It just seems that the picture you paint now versus the picture you painted of them in the initial letter to Evan is different. Like you barely knew them when you wrote your letter, so I am wondering how much time did it take for you to get to know them enough to know they both were wrong for you.

      5). Do you feel that you yourself did anything that caused the relationships to not work out?


      1. 8.2.1

        I knew the clingy guy a couple months (we were never intimate) when I wrote this… more or less, it was last Fall so now I don’t have the precise timelines in mind any more. I knew the other guy   for almost 10 years as a friend and entered the equation as more-than-friends about a month after I met the clingy one.

        The clingy guy was definitively anxious preoccupied. I noticed that right away. I have no problem dating someone mildly anxious preoccupied, but must be reasonable. Initially it was very reasonable but things started to change especially when I had to be out of state for work for a week.
        Just as an example (there were many):   after a while, even if  we would talk over the phone (voice) for say 30 minutes at night, which we did very often, he would still complain I was not chatting enough if I did not keep texting him. In other words minutes after we talked over the phone he was still expecting me to keep texting him and feeling I was disconnected if I did not. This is typical anxious preoccupied behavior: the child that wants to see the caregiver is CONSTANTLY there for them, who gets anxiety if they lose sight of the caregiver.
        He was rarely  starting any texts, but would subtly complain I did not start them myself : “you are not very talkative  tonight so I bid you goodnight” he would say for example, even many hours   before his bed time  and after I called him and talked for over 30 minutes – this is a bid for attention clearly. I explained in a kind way several times that I have to clean, cook etc at night, so I was not able to text all night. Initially he did not seem to expect this level of constant communication but then it turned out he wanted someone that really kept reassuring him, and he started complaining more and more that I was not talkative enough. Even when I was at work!
        Also another example, he asked me to be in an exclusive relationship after 1 date face to face, meeting for coffee.
        Many many other things pointed to the fact that he was anxious preoccupied, too many to report here. Suffice to say I am sure that was his attachment style and initially I thought he was mildly anxious preoccupied but then turned out to be far more extreme even with extensive daily communication and meeting weekly.
        The picture I paint now is after I knew them better so yes   it is different. Most people when they start a relationship only have limited information about someone, it is the nature of things. Still, you have to make decision based on what you know at that time. So yes my assessment of both men was wrong, neither was “perfect” for me but at that time, I could not predict the future and until then both men showed a lot of potential and a lot of interest in me. They both treated me very well and at that time there were no major red flags.

        This is a situation that may be common when you are on a dating site and start seeing different people: how to eventually choose one limiting the hurting on the others. This was the point of me writing to Evan. I knew Evan’s  response would come too late for me personally.

        Even if the first guy was not clingy I would have still allowed the 2nd guy to enter the equation  because he entered when I did not really know well the 1st guy (a month only, few face to face meetings) and we were not exclusive, even if he had asked after 1 date.
        Like Evan always says it is always good to evaluate options at the very beginning when you are just seeing someone. So many times it does not turn out to be a relationship or a good one. I am not a cheater. But even if I really like someone, when I and single and ready to start a new relationship  I try to meet different people, try to see their long term potential and I do not consider it a relationship until both parties know each other well and call it an exclusive relationship. So evaluating your options makes sense even if at first you “think” you found a perfect match. You cannot know it is truly perfect until much later.

        I do not have any regrets on how I treated either man. I was always affectionate, warm and respectful with both and tried to use an objective eye to the best of my abilities.

        I absolutely love Evan’s response here: telling someone you like him / her but you cannot see yourself spending every day of your life with them. PERFECT wording.   Exactly what I was looking for when I wrote to him. Golden and spot on. And I will keep this line in mind because it is honest (I am looking for long term), classy and a million times better than the typical slow fade you see so many doing.

        1. jeremy

          Ah.   I stand corrected.   The behavior you describe is, indeed, very insecure and more than simply a guy who likes you more than you like him.

        2. ScottH

          Rose said:   “They both treated me very well and at that time there were no major red flags.”

          “Also another example, he asked me to be in an exclusive relationship after 1 date face to face, meeting for coffee.”

          Don’t you think asking to be exclusive after the first date is a red flag?

        3. Rose

          ScottH: Asking exclusivity after one date is a flag of anxious preoccupied attachment style. But as I said I personally can handle that TO SOME EXTENT. I will take a mildly clingy guy any day over an aloof distant avoidant. That is just me. Avoidant behavior = massive red flag FOR ME. I like affection so aloofness is the worst red flag for me. A little too needy = fine. Excessively needy = not fine.
          Also if you rule out everyone for a single thing they do wrong you are going to be single for a very long time. Like Evan always says, you have to compromise on something. And we all make mistakes.
          I know what compromises I am willing to accept. I am entirely happy of how I tried to see if it could work with that guy. It did not, ok, no big deal. If he a bit clingy and insecure  but not to that extent, I might have chosen him instead. But you can’t change anyone you can only observe and decide based on what YOU  are looking for.
          The point of my letter to Evan was how to tell a person that you don’t want to go on further,  at a time when he made no deal breakers for you.

          Most people either take little excuses (example “I am too busy right now for a relationship”) or do a slow fade.

          I treat others like I want to be treated so I try to learn the most respectful ways to handle any situation. This was the point of my letter and it has little to do with  those two guys and their specific actions.

      2. 8.2.2

        Hi Rose,

        Yes he was very insecure.

        I have book marked this post for myself in the future, so if I am ever feeling insecure I can remind myself that maybe she does like me I just can’t see it.

  9. 9

    Hi the only thing I would add here to Evan’s advice is that there is absolutely no need for the OP to tell the guy she is saying goodbye to that she has chosen someone else. Just keep it short and sweet as per Evan’s script. End of story.

  10. 10

    You sound like a balanced and considerate girl, Rose.   Good on you for wanting something better than the slow fade.   May there be more people like you :).   I hope you find the fulfilling long term relationship for which you are searching very soon.

    Just to satisfy my curiosity, I do have a few questions.   I shall certainly understand if you choose not to answer them.

    1) You’ve mentioned “I’m not a cheater” once or twice.   Do people accuse you of this?   In my book, if you’ve not agreed to be exclusive you are not a cheater.   However, you did say that you avoided questions from both men about whether you were seeing other people.   How long did you do this?   Just at the first few dates or even later?   If one had explained calmly after a few dates that he only believes in seeing one woman at a time and expects the same of the woman, would you then have told the truth, wished him well and focused on the other guy?   Or would you have found this request unreasonable and continued seeing both until you figured out which one had more potential?

    2) You say you were not intimate with the insecure guy.   Were you intimate with the other guy while still seeing the insecure one?

    3) Was the insecurity the only problem with the first guy?   I.e. if had changed his behaviour and become more secure around you as time went by, would you have kept him?   I wonder if he realised how, in demanding more of your time, he was actually ensuring that he would cause irritation and so eventually get less of it.   Wonder if anything would have changed if you had point blank told him that you liked him but his constant need for attention was sabotaging any chance you had.   Anyway, it wasn’t your job to fix him…

    No judgement is intended one way or another…I am, as I said, simply curious 😀

    1. 10.1
      Emily, the original


      Wonder if anything would have changed if you had point blank told him that you liked him but his constant need for attention was sabotaging any chance you had.

      By the time a woman feels the need to tell a man his constant attention is killing her interest, she’s actually probably lost interest. This would be true for a lot of women. Not all, as Rose mentioned she didn’t mind some level of insecurity/anxious behavior.

    2. 10.2

      Nobody I dated ever accused me of cheating.
      The insecure guy was not even directly placing demands but getting annoyed and sulking if I did not reach out all the time. This is even worse than demanding because there is also the lack of communication problem and when I would point  out that I was busy he would get passive aggressive.

      It is impossible to say what one would do if someone else was different. You have to take the package as a whole. Making hypotheses on how the package would be if a certain part was different makes no sense to me. And it is impossible to say since you don’t know “how different” the part would be. Ultimately what you see is what you get. Of course at first you cannot possibly see every single part of the package which is why at first I thought he was absolutely great.

      1. 10.2.1
        Emily, the original

        Hi Rose,

        Just out of curiosity: Which guy was hotter? Did that have anything to do with your decision to pick one or the other? Or which one were you more attracted to? (That might have had nothing to do with your decision. For some people, it may be a factor.)


  11. 11

    The insecure guy was demonstrating passive/aggressive behavior. However, he may have been intuitive enough later on to sense there was someone else in the picture. This all seemed to happen rather quickly and, since I think she made it clear she wasn’t sleeping with either of them, it’s not as if she could have ” cheated” on either of them. I think.

    The thing is, is it’s best to be honest and, if necessary, blunt. Typically, someone coming out of a relationship is vulnerable and prone to rebounding behaviors–others are clingy if they got hurt. It’s best to not date immediately after the end of an LTR. Relationships are not the same as riding a horse or a bike. Your mind and body need time to heal and recoup from it–particularly if you happened to be the one who got dumped.

    Thus, if I’m shopping around, I make it clear from the get go and leave it up to the woman to decide whether or not she wants to take part in my shopping spree. If she does and ends up being put back on the shelf, she knew from the beginning where she stood. It’s one of my “shit tests” because I want to avoid a woman who might become clingy and jealous later on.

    Before I have sex with anyone, I want to know if it’s exclusive. I don’t want an std and I don’t want to be where some other guy is currently making his home. After all the very, very many women I’ve known–beginning at age 15, I’ve never had an std and I don’t want one now. Condoms do not protect you from herpes, for instance, and men can and do get (mostly throat cancer) from HPV and there are no tests available for men where HPV is concerned.

    Yep–I’m a mythical unicorn and get away with it, YMMV.

    1. 11.1
      Emily, the original


      Thus, if I’m shopping around, I make it clear from the get go and leave it up to the woman to decide whether or not she wants to take part in my shopping spree. If she does and ends up being put back on the shelf, she knew from the beginning where she stood. It’s one of my “shit tests” because I want to avoid a woman who might become clingy and jealous later on.

      I think most women will assume you are dating around until you have the exclusive talk. Women will know you have other options simply by meeting and interacting with you. They can tell if you are in demand. You don’t have to announce it. And people (men and women) don’t like “shit tests.” In light of discovering that’s what you are doing, do many women then decide to get in their car and go to another mall   ??

      1. 11.1.1

        I’m almost always asked, Emily by date three for sure. And no, no woman has ever gotten up and left a date. The 45 minute coffee or wine date usually stretches into two hours or more. My sitter got used to it rapidly. They always proffer their phone numbers at the first date–I never have to ask a woman for her number, never have. I’ve never, in fact, made a pass at woman. I am that rare unicorn. A few times I’ve asked for the check and left usually because the woman’s pictures were way out of date or she was so obviously bitter about her last relationship that there was no reason to be around her.

        And it’s a nice place to be, thank you very much. See, it’s kind of like being a hot woman. You get to pick and choose. Some women have issues with that. They aren’t suitable–for me.

        1. Emily, the original

          I’m calling b.s., dude. If you were doing that well, you wouldn’t be on a site for dating advice. You’d be too busy fielding offers.

        2. Robert

          Emily–your opinion doesn’t matter to me in the least. It would be simple enough to let you see my FB page. Evan can google my name since it’s in my email and see where I’m from and who my family is. My grandfather invented the automatic sheet fed printing press while working for his father. My first wife’s father owned a paper company–she and her sister own it now   my second wife’s father and uncle owned the largest banking software company in North America

          I came on here from a google search. This site is for women not men. I’ve had fun reading the comments of those women. Some are sweet and nieve. Others, like Stacy2 s lend credence to what the red pill types talk about. Then there are those such as yourself who don’t get it at all and never will–the old woman with cats theory. What I’ve noticed while wandering through his posts is how looong some of you have been here–you apparently aren’t taking his advice to heart and just want a place to complain and spoil other women’s chances. And then there’s you–a noticeably bitter woman

          Notice I don’t bother to support small men and their crying–nature does that to some men. Just as nature makes some women ungainly tall and manly–like stacy2. The n there are abnormally tall men who like abnormally short women–because they have small pee pees and reason a small woman won’t mind because she’s small.

          Nope. Your opinion means nothing to me. My purpose is to have a bit of fun and assure women they have a chance, but only when they become realistic about who and what they actually are–just as Evan tells people to do. I also came on here, as I said in my first post, that being here was a way to kill time while taking a break from work.   Highly intelligent people enjoy learning and one of my favorite “sports” is watching people engage with one another.

        3. Emily, the original


          What I’ve noticed while wandering through his posts is how looong some of you have been here

          You can’t tell how long any of us have been on here. There aren’t any dates on the posts.

      2. 11.1.2

        See, Emily, my parents were movie star gorgeous. At age 30 I bought a four bedroom, two fireplace, 3400 sq. ft. house in an inner city, toney neighborhood that’s paid for and I still own. I live in it now with just my son and our dog and the occasional nanny and my daughter who comes for visits from johns-Hopkins medical school. My son attends a very exclusive private military academy and I pretty much do what I want.

        I drive vintage roadsters–a new Porsche or something would make me look like a midlife crisis guy which I’m not. Besides–I restored them for the fun of it and gave one to my daughter. Im stylish to a fault, have superb manners, extremely well educated–I didn’t go to college to learn a “trade”, I’ve been successful. Married two heiresses and only had children with the second one. Like hot women, I have female orbiters and female friends who really are just my buddies. I get my advice from them and listen to their views on women I date.

        1. Persephone

          Wow.   Narcissist personality disorder. I really try hard not to say anything negative about anyone but Robert, you’re over the top.

  12. 12

    And Emily, I wholeheartedly embrace Evans view that people need to be realistic in their expectations. They shouldn’t be looking for the rare unicorn–not that they don’t exist, but they can pick and choose who they want. And if you were in that boat, you wouldn’t be here.

    1. 12.1
      Emily, the original

      Okie. dokie.

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