My Insecure Boyfriend Is Trying to Scare Me Off of All Men Besides Him

My Insecure Boyfriend Is Trying to Scare Me Off of All Men Besides Him

Hello Evan,

I have kind of an unusual question, and I was hoping to get your take on it. I’ve been dating my boyfriend for three months now, and there are lots of things I like about him. He’s really smart, and makes me laugh, and we both have the same values. However, he regularly tells me how sorry he feels for single women in general, and talks about how particularly sorry he is for women in San Francisco (where we live). He constantly talks about how other men are such jerks and players, and how he feels so much pity for his women friends, for his female boss and co-workers, and for all the women he dated before me. It is starting to make me uncomfortable.

A little background, I’m 30 and just moved home to San Francisco from New York City about 8 months ago. Sure, like any big city, San Francisco has its share of flaky dudes, or men too busy for a relationship. But there are lots of smart, interesting guys here, and there are actually more straight men than women because of the tech companies. Compared to NYC, San Francisco seems like a square deal. A lot of my guy friends who work in tech here complain about how hard it is to meet women.

I’ve tried to tell my boyfriend that dating here (and anywhere) is challenging for both sexes, and it’s probably best to have a little empathy for everyone. But he doesn’t seem to want to drop the issue. I’ve asked if this is some kind of strange sales pitch, and asked why he brings it up so much, but he just insists he’s just a nice guy who feels really sorry for women. I can’t tell if this is genuine concern, or it’s some kind of weird high-pressure commitment tactic. It usually comes up when I’m busy or he’s annoyed about something, so it seems like the latter. But there’s no need to pressure me – I’m already committed to him! And anyway, wouldn’t it be best for everyone if I date him because I like him, not because he’s managed to scare me away from the dating scene?

One last thing – my boyfriend is completely bald. I think he’s cute, but not every woman loves bald men. I feel like if I talked about bald men the way he talks about women, he’d probably get uncomfortable too. Part of me wants to turn the tables and say things like “I feel so sorry for bald men – it must be so difficult for them to find love when women prefer hair.” But that just seems mean and unproductive!

Should I cut this guy loose and find someone who isn’t into scare tactics, or do I just assume the best in my boyfriend, and that he’s got some kind of misguided knight-in-shining-armor complex, and try to see the good in it?

Seeking the Bald, Honest, Truth,

Every once in a while, I get a letter that I’ve never gotten before. Thanks for making my day, Sarah. Unfortunately, I don’t have all that much to add to your analysis.

He’s a nice guy who feels really sorry for women.
He’s insecure about being bald and a “nice guy” since many women don’t like both traits.
He’s trying to put himself on a pedestal as a paragon of virtue, thereby “scaring” you from the broader dating pool of Silicon Valley Tinder-ing D-Bags.

If I were you and I actually liked this guy (after all, he IS your boyfriend), I would put it to him straight.

I would bet that the answer is D) All of the above.

So if I were you and I actually liked this guy (after all, he IS your boyfriend), I would put it to him straight:

Please, take yes for an answer. I’m already your girlfriend. And every time you tell me that you feel sorry for women, it makes me feel really awkward, as if I told you “I feel sorry for bald men because women judge them unfairly. Aren’t you lucky you found me?” Then listen to his reaction. He will hopefully admit some level of insecurity and you can bond over getting past this hurdle. And if he doesn’t, and this annoys you that much, then, by all means, you have the right to find a guy who doesn’t see fit to remind you all the time that you’d be lost without him.

Oh, and for extra reading on the pathology of being the “nice guy,” pick up a copy of Dr. Robert Glover’s “No More Mr. Nice Guy.”

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  1. 1

    An interesting letter, with an always excellent answer by Evan.

    Why are women always so afraid of actually communicating with men?

    I always hear women say that men never want to talk, but I have found the exact opposite to be true.   The majority of women seem to falsely believe that men are mind-readers.   Or the woman may talk at him and not to him.

    I sometimes wonder if it is because woman are afraid of being rejected (emotionally, intellectually, etc.) if they convey their feelings to men.
    Men have to constantly get rejected when asking women out.   I think it is time that women had to endure the same (equal rights, no?).

    1. 1.1
      Karmic Equation

      I guess it depends on what you mean by being “rejected” — Do you mean she’s afraid the man might dump her if she conveys her intellect or her emotions?

      In that nebulous time between when a relationship has begun (you’re bf/gf) and until he says “I love you” to her, a woman is often afraid to “lose” him. And she often won’t communicate truthfully about her feelings.

      It’s the fear of losing him that keeps her silent on important issues. Except the “thou shalt not be friends with thine ex” decree. That one they’ll convey in one way or another.

      I think that’s the wrong way to go. During those first, say 6 months, of a relationship, that’s when she should be the LEAST afraid of losing him and worrying if this relationship is “heading somewhere” and trying her best to make it go there.

      Instead, she should be spending that nebulous time evaluating him and asking herself if she can deal with a lifetime of his <list his faults here>.

      OP should ask herself, “if my bf doesn’t change this behavior, can I accept it for the rest of my life?” If the answer is no, then she definitely needs to find nice a way, during an opportune time, to convey to him that this specific behavior needs to change. Bringing it up out of the blue will never work. If the answer is yes, she lets it go. If she’s not sure, put it on the back burner and revisit when another bad behavior reveals itself. Then ask herself if she can live with BOTH those behaviors for the rest of her life. Keep doing this triage.

      Eventually, she’ll either have a very long list of things she can’t live with — in which case the answer is clear, and she should exit the relationship. Or a very short one — in which case she needs to figure out how to address or ignore the behaviors.

      What she shouldn’t do, which is what she’s already doing, is go on the “reassurance” — assuring him that she’s committed despite his behavior. That doesn’t solve HER problem. It only reassures him.

      I’m of the opinion that during that time before “I love you’s” are spoken, both parties should be in evaluation mode, not get so emotionally attached that you can’t envision exiting the relationship.

      Evan says “a man’s not real until he’s your boyfriend.” I would add that “a relationship’s not real until both parties have said ‘I love you’.”

      1. 1.1.1

        Karmic Equation said: “I guess it depends on what you mean by being “rejected” …”

        Belittled or trivialized for her opinion, for expressing her feelings, etc.
        I see a lot of guys do that to women/girlfriends/wives.

        Maybe I just answered my own question there.   🙂

        I’m a talker, I can keep up with the best of women, and introspective, so perhaps that is why I don’t understand why people sometimes don’t just communicate.

        1. Karmic Equation

          Women need to exit relationships where they’re trivialized or belittled.

          The man that does this, husband or not, does not deserve that woman’s love or devotion.

          It’s unfortunate when kids are involved or if the woman is financially dependent on a man who does this.

          Women need to choose their husbands well…for good treatment, for honor, for integrity. The truth of the matter is that many men can be great boyfriends with whom you can have fun and excitement. But don’t marry that guy if you know that he does NOT treat you well, does NOT have honor or integrity.

          Good boyfriends don’t always make good husbands. A lot of men who have a zest for life often have no sense of responsibility. A woman HAS to be discerning and not let “love” cloud her judgment of a man’s character, or lack thereof, and go marrying the wrong guy because of sunk costs or ticking clocks.

        2. DeeGee

          Karmic Equation – I agree completely, good post.

          Most men need to work on themselves as well, and women shouldn’t let them get away with poor habits or traits.

  2. 2
    Mrs. Newlwed

    Dump him or regret it. I once dated a man who complained about all women including his “crazy” Mother and “mixed up” sisters. Whats that you say? I dumped him in …couples therapy! Without personal enlightenment he won’t man up and tell you the truth that he feels like crap inside. PS. I, too live in San Francisco, Sarah and agree with you there are tons of straight men here!   I met   my husband and married here.

  3. 3

    He’s insecure. And i can tell you have a pretty good self esteem. I dated a guy similar to him and I was offended because I coukd see what he was trying to do and I saw it as the start of an emotionally abusive relationship so I broke it off with him. Some men will make themselves feel better by passively aggressively putting you down and calling it love.   I agree with Evan give him a talking too and see what he says and if he changes for the better but if the behavior returns because people dont generally change if they dont want too then show his bald head the door.

  4. 4

    It almost sounds like he wants to feel sorry for women. Like it makes him feel better to feel sorry for women because of his own insecurities. I wouldn’t say this guy has the healthiest attitude toward women. I would consider this a red-flag situation. Pay attention to his other beliefs and thoughts about women. Does he say anything else about women in positive ways that goes beyond how sorry he feels for them?

  5. 5

    My advice would have been absolutely DON’T turn the tables and make the bald parody (it’s true that would be mean and unproductive).   I liked the way Evan managed to make the comparison without actually throwing it in the boyfriend’s face.   I also really liked the writer’s comment “wouldn’t it be best for everyone if I date him because I like him, not because he’s managed to scare me away from the dating scene?” so maybe that is an opening to another conversation.   But since the writer has already attempted to talk to her boyfriend about why he insists on bringing it up, and he’s still bringing it, I’m thinking maybe it’s time to decide if she can just let those comments roll off her back or if this is a deal-breaker.   If he’s otherwise a great guy, I’d probably just start tuning that one thing out and accept that in long-term relationships there are always a few things that just don’t get resolved, and you decide to just accept each other.

  6. 6

    A guy that pities women and feels really sorry for them would raise so many red flags, I’d be running in the other direction. I want a man who respects women rather than pities them, who feels joy about the subject of women in general rather feeling sorry for women. To me it doesn’t read insecure. It reads: this guy has issues and no genuine   respect for women. IF he is legit in his feelings and he’s constantly talking about how he pities them and feels sorry for them, the universe will show him plenty of examples of women who are truly in situations deserving of pity or sorrow. I wouldn’t hang around long enough to be the next “example” of a woman deserving of pity and sorrow, for the universe is sure to bring him what he’s focused on. Don’t let that be you.

    AND, why exactly does he feel pity or sorrow for every woman he dated before you? Another huge red flag that doesn’t read insecure to me. It reads narcissistic jerk who feels like he’s the catch that got away, and all those women who let him get away are deserving of pity for not being bright enough to see what a catch [he thinks] he is.

    A truly nice guy does not need to insist he’s a nice guy. You will see it in his attitudes and actions, about women and other subjects. With a truly nice guy, you wouldn’t be writing in asking this particular question. Perhaps you would have had one conversation where the subject of dating life in the Bay Area (or in general) came up and where he expressed views similar to your own empathetic views. It would not be brought up over and over.

    Ohmygosh, so many red flags. Run. Away.

  7. 7

    Hey Evan,

    I’m a long time reader, and I finally decided to comment on this post because I used to have a similar attitude to the man in this letter. “No More Mr. Nice Guy” was the most important book I read on that topic, and it helped me understand why I felt bad for women and resented other men. Once I tried implementing his advice, I felt happier and my relationships became healthier.

    I feel like this man is kind of bewildered that he is in a relationship. He may lack confidence and internally doubt that any woman would want to date him.  Hopefully, your advice will help the author communicate to him that his worldview isn’t realistic.

  8. 8

    Let’s be honest. Your boyfriend is very insecure. He’s finding creative ways to boost his self-esteem, despite not doing so in a positive way. It’s obvious that he doesn’t respect women.

    If you want to continue to stay in the relationship, I suggest that you confront him. This type of behavior is unacceptable, so there’s no need to tolerate it anymore.

    He should have seized the opportunity to focus on his insecurities, instead of jumping into a new relationship head first.

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