How Can I Stop Feeling Guilty After Breaking Off a Relationship?

How Can I Stop Feeling Guilty After Breaking Off a Relationship
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This is going to sound weird and conceited and awkward, but please bear with me. I’m a 28-year-old man, and from what I’m told, I’m a “catch”. I’m well-employed, fairly handsome, and what my friends call “accidentally charming”. I’m incredibly lucky for everything I have in my life, so I’m not complaining about myself.

My problem? I can’t date normally, because the women I date get attached and I don’t have the heart to let them down. This has happened my entire life. There are women (who were then “girls”!) from fifteen years ago on through present day who consistently call me the one who got away, and it makes me feel awful. I’ve never once even briefly dated a woman who hasn’t come back days/weeks/months/years later to tell me that she “lost me”.

It makes me feel terrible, so I stick around in bad relationships. I know I do it, but I can’t bring myself to ruin another person’s feelings until I’ve been there long enough to start hating myself and my life more than I care about her. I’m in this cycle now – my current girlfriend is a sweet, kind, fun woman who’s utterly dedicated to me and who I can’t see myself with long-term. She’s been through many bad relationships, and to her, I’m “The Guy.” But I’m almost thirty and I know I don’t want to spend the rest of my life with her, so every time I’m with her, it’s bittersweet. What can I do to break this cycle and end relationships without lingering feelings of guilt?

Jay

Thirteen years ago, I dated somebody casually for about a month. Zoe. Lovely woman. Smart. Nice. Great sex. Different senses of humor and sensibilities. I didn’t see a future with her, per se, but I was definitely enjoying myself and thought she was, too.

Thanksgiving rolled around and I recalled that Zoe had lost both of her parents separately in the past year. As a guy whose father died at a young age, I was particularly sensitive to this issue, and even though I wasn’t her boyfriend, I called her on the holiday to see how she was holding up.

The second you don’t see yourself with your girlfriend in long-term, break up with her and let her find another guy who does.

I was just doing what nice, sensitive guys do, right? What I didn’t calculate was that, in taking that intimate emotional step, I pretty much induced this woman to fall for me. I was no longer the boy toy; I was suddenly acting like a boyfriend.

That’s why the second the conversation was over, I knew I had to break it off. And I did. In person. Upon which she said:

“I think this makes me like you more than I already did.”

“I hope this doesn’t mean we can’t have sex from time to time.”

Yes, this was one story in which doing the right thing led to a positive outcome. But the truth is, Zoe couldn’t handle our FWB relationship. We only got together one time after that.

I thought of this story when I read your letter, Jay, not because I doubt that you’re a “catch,” but because I find it almost amusing that you don’t know how to break this cycle.

If you’re going to feel guilty about anything, let it be that you’ve been wasting lots of women’s time under the guise that you’re too “nice” to hurt them.

Don’t get me wrong: you’re not alone. I routinely coach women who have trouble breaking things off from men. More commonly, I field complaints from women who date cowards like you who don’t have the spine to break up when you’re never going to marry her.

So there’s your answer, Bittersweet Jay.

The second you don’t see yourself with your girlfriend in long-term, break up with her and let her find another guy who does.

Doing so makes you nice. Not doing so makes you cowardly.

If you’re going to feel guilty about anything, let it be that you’ve been wasting lots of women’s time under the guise that you’re too “nice” to hurt them.

Sorry, but that’s not true. You’re just being selfish.

Readers, please share this someone who needs to hear this today.

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Comments:

  1. 21
    Stacy

    ‘where noone he dates seem good enough’

  2. 22
    Stacy

    And to respond to Christine earlier: most of the time when I go out, the woman (7 times out of 10) is clearly more attractive than the man. The other times, they are roughly equally attractive (again, based on my observation)…totally works better that way.   Although  I don’t consider hollywood as real life, I think it at least depicts this clearly…old spent guy with beautiful young woman…The Donald Trump example is classic. You hardly, if ever, see the opposite (unattractive older woman with really hot young guy both married and in love).   I consciously do not date men who are more objectively attractive than me (although I used to in my 30s) and they just love me but I always turn them down. My ex husband was hot/a model and honestly, I agree with Chris Rock – men (most) are   as faithful as their options.   We women can handle being hot way better than a man can. FACT.

    1. 22.1
      Adrian

      Hi Stacy,

      you stated, “most of the time when I go out, the woman (7 times out of 10) is clearly more attractive than the man.

      I remember back when I was just a reader and did not comment you had made the same statement. At the time my observations were completely different, I always saw more attractive men with lesser attractive women.

      Now I realize that there seems to be a general pattern or traits of couples that have either the man or the woman being more attractive and 99% of the time it comes down to the money.

      I have noticed that when the man is of low financial status then he is in a sense taking on the female role of trading his looks for financial stability. These are your really handsome men, or maybe men who are 10 years younger that you see dating women who are not as attractive, overweight, or much older.

      When I see a woman that is two leagues or more higher than a man in the looks department it is usually for the same reasons. The woman seeking financial stability-with the caveat of her just being burnt out on the normal type of guys she dates and is therefore giving this overweight or unattractive guy a chance.

      I say more than two leagues because a guy who is 5 dating a woman that is a 6 is not uncommon and visa-versa if they are on the same financial level. A 5 dating a 7 though a little more rare is still   not to uncommon if they are on the same financial level. A guy who is a 5 dating a woman who is a 8 and they both are on the same financial level I have never seen.

      This is why when science says that most people date within their own attraction level (give or take 2 levels difference) I agree as long as both people are on equal grounds financially and status wise.

      1. 22.1.1
        Stacy

        Adrian, I agree with your post.

      2. 22.1.2
        Stacy

        After thinking about your thoughts on this, I would have to say that I completely agree.  There is usually a trade off involved when the disparity in looks are significant.

         

         

  3. 23
    Stacy

    Should be ‘used to in my 20s’…I am currently in my 30s.

  4. 24
    GoWiththeFlow

    Jay,

    Its in the normal range of human emotion to sometimes feel bad or guilty when you break off a romantic relationship.   The key is to not dwell on it and move on.

    The thing I don’t get is why you stay in a relationship with someone until you are miserable just to avoid the unpleasantness of a break up.   This isn’t fair to the woman, yes, but it’s not great for you either.   Learn to face and act on your true feelings earlier.   Maybe then the breakups won’t leave you feeling so guilty.   It’s better for both people in the long run.

  5. 25
    Nissa

    Jay,

    Please consider reading No More Mr. Nice Guy by Robert Glover. You sound a lot like the guys he talks about – not jerks, but guys who act inappropriately because they don’t have good personal boundaries. For example, not breaking up with someone even though you are not into them, because they like you, is an example of poor boundaries. Glover gives a lot of good information about how to learn how to get what you want & need, without hurting people unnecessarily. FYI, I’m not associated w/Glover, I just think it’s a good reference book for men.

    1. 25.1
      John

      Nissa

      This is the best advice I have read so far on this post. No More Mr. Nice Guy is a great book for guys to read.

  6. 26
    Marika

    Everyone, please give the guy a break!

    I can’t relate to a lot of his letter, been through many break ups myself, some initiated by me, some by them, and have gotten over all of them (and I dare say they have too), but I can completely relate to the idea of not wanting to hurt someone’s feelings. If you can’t relate to that, then you’re knocking on the door of being a narcissist. It’s tough when someone is clearly into you and you have to break up with them. It’s all part of dating & life and he does of course need to pull the band aid off and just end it with this woman, but why all the harsh comments? He’s just a young guy trying to navigate dating while trying not to hurt anyone’s feelings. Naive, yes, but all the other things he’s been accused of, no.

    The venom in some of these comments is quite amazing.

    1. 26.1
      Chance

      I think a lot of the venom comes from the fact that these women seem to be offended by how this guy appears to think of himself.   Apparently, he’s either too confident or delusional.   Okay… So what?   Indeed, it is fascinating that this would cause some women to be  rocked by the sudden impulse to “put him in his place”.   I would argue that it says more about them than him.

      1. 26.1.1
        Emily, the original

        Chance,

          Indeed, it is fascinating that this would cause some women to be  rocked by the sudden impulse to “put him in his place”.

        Wrong. This is what he wrote: I’ve never once even briefly dated a woman who hasn’t come back days/weeks/months/years later to tell me that she “lost me”.

        Does not sound delusional to you? Trust me: if the OP was a woman, you’d have questioned her. “What are you, Megan Fox?” He makes it sound like he has never been dumped. There is not a person on the planet who hasn’t at some point wanted something more from someone than that person wanted from them. It’s part of the human condition. We’re not putting him in his place. We’re calling him on his bullshit.

        1. Chance

          Either way, it seems strange to feel compelled to respond to him.   Why badger someone who you feel is delusional?   What does it have to do with you?

        2. Chance

          Btw, I wouldn’t have questioned the LW if he was female solely because I thought she was delusional.   For example, you’re delusional about the level of sustained chemistry that you want and expect to have with a partner, but I don’t bother you about that.   It’s your business, and you aren’t proposing or promoting anything that is unfair, so I say live and let live.

        3. KK

          Chance said,

          “Either way, it seems strange to feel compelled to respond to him.   Why badger someone who you feel is delusional?   What does it have to do with you?”

          How exactly did Emily  badger him by stating her opinion? She gave an opinion. So did I. So did you. For such an opinionated little thing, you sure have a lot of double standards and rules for when it’s appropriate for anyone else to give an opinion. If anything YOU are the one  badgering people who don’t agree with you. Keep beating your little drum about how unfair it is to be a man. Wow. Manly. I agree with Evan. Man up or shut up.

        4. Chance

          The view from between your ears is an entertaining one, k.

        5. Emily, the original

          KK,

          Thank you for defending my comment.

          There are certain commenters I have decided to no longer engage with/respond to as I believe their tone is negative and red-pill like. (I am not referring to you.) I don’t think that kind of dialogue helps each side of the gender aisle understand the other.

        6. Shaukat

          Emily, I am, however, interested in hearing why you think the Letter Writer’s delusional beliefs (assuming he is delusional on this point) are relevant. Even if what you’re saying is true, it still doesn’t detract from the fact that he believes that he has a problem when it comes to breaking off dead-end relationships. That’s the real issue, not whether he  truly is  a Casanova.

        7. Emily, the original

          Hi Shaukat

          Emily, I am, however, interested in hearing why you think the Letter Writer’s delusional beliefs (assuming he is delusional on this point) are relevant. Even if what you’re saying is true, it still doesn’t detract from the fact that he believes that he has a problem when it comes to breaking off dead-end relationships. That’s the real issue, not whether he  truly is  a Casanova.

          Because something doesn’t add up, and if he lacks   self-awareness, he will not be able to understand his role in these dead-end relationships. I am just guessing that the OP is delusional (and that may be too strong a word). I have an acquaintance who is always telling me about all the men who are making eye contact with her in public and who are asking for her number, yet she never has a boyfriend. So either she is sabotaging these opportunities or she is lying. Either way, something is off, like something is off with the OP’s description of himself. If what he says is true, what is he doing to make all these women pine for him years later? Is he making them think at some point in their interactions that he’s “the one”?

        8. KK

          Hi Emily,

          “There are certain commenters I have decided to no longer engage with/respond to as I believe their tone is negative and red-pill like. (I am not referring to you.) I don’t think that kind of dialogue helps each side of the gender aisle understand the other”.

          I hear ya! : )

        9. Chance

          Emily, it still doesn’t appear that what you’re taking issue with is relevant to the LW’s dilemma.   Even if you believe that it helps him to possibly assess the issue from this new angle that you presented, the tone of your comments relating to him don’t remotely sound like you are coming from a place of trying to help.

    2. 26.2
      Adrian

      Hi Marika,

      I know that you are new to commenting here (I’m not sure if you are new to the site itself).

      Unfortunately the petty infighting is one of the darker sides of our little family here on EMK. For the most part I do honestly think everyone means well.

      I just usually avoid the arguments all together by refraining from commenting; sometimes some very good points or new insights are brought out by these sub-debates and sometimes it is just more about being proven right than it is about the truth.

      Either way it will pass soon. And compared to what I have witnessed on other relationship blogs, EMK’ commenting community is by far the best. They can get a little rough with their adjectives but never have I seen the regulars get nasty or hateful.

      Since you are a new regular commenter I just wanted to assure you that this is not as bad as on other sites and it doesn’t happen very often. I hope it does not cause you to comment less here since I really do enjoy and value your insights on dating issues.

      1. 26.2.1
        GoWiththeFlow

        Adrian,

        “I just usually avoid the arguments all together by refraining from commenting; sometimes some very good points or new insights are brought out by these sub-debates and sometimes it is just more about being proven right than it is about the truth.”

        My thoughts exactly.   Although a debate amongst commenters may not ultimately change my opinion, it’s always beneficial to see a strong counter-argument, or to just know that not everyone agrees with me.   It keeps you humble 😉

        At the very least I try not to feed the trolls.   But last night I couldn’t help myself!

  7. 27
    Marika

    Thank you Adrian & GoWithThe Flow,

    I’ve been reading EMK’s stuff for a while now, but it’s true I’m a reasonably new commenter. I shouldn’t be surprised, really and I know there are far worse comments out there, but it saddens me that when people reach out for help, on a site where we’re all here for the same thing, that people

    Get

    So

    Angry / Judgy!

    As well as often missing completely the point of the post or question. Whether this guy is delusional about his attractiveness is beside the point….

    (cue angry debaters 😉

    If we could all take some time in this season of goodwill to maybe be helpful & compassionate in our comments, rather than all vitriolic & like 5th grade debaters, that would be nice……that’s my Christmas wish 🙂

    Very happy holidays, all!

  8. 28
    Marie

    Look Jay, I’m not here to judge your character. My advice to you is, nothing risked, nothing gained. If you date safe, if you don’t risk your heart, how will you really find your soulmate?   How will you really fall in love?   Are you going to one day settle for one of these woman you only care for so-so because she is unlikely to leave you?   That sounds really like a bland existence.   My husband and I truly love each other. But we had to risk emotionally first. So what if you have a hundred women pining after you? That does not make you a success in love as I define it. That makes you a loser if you cannot find or be with the woman you love.   I would rather have my husband than a hundred men pining after me.   He is the one I want. To find and have the one you truly love and desire, that is the measure of true romantic success.

  9. 29
    Alisa

    This guy sounds REALLY awful.   No, you do not call a woman up around the holidays to ask her how she is if you have no romantic or sexual intent.   And if the woman lost her parents, it’s pretty sick to be calling her up with a SEXUAL intent.   Is this guy a joke?   I can’t believe that he thinks he is above these women.

  10. 30
    Lahey

    Evan’s response to this was amazing.

  11. 31
    Marina

    Certain men keep women that are not good enough for marriage in the “friend zone” to boost their self-esteem.

     

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