What Can I Do to Make My Boyfriend Feel Better About Himself?

What Can I Do to Make My Boyfriend Feel Better About Himself

I love your blog. It’s nice reading a no-bullshit point of view with facts to back it up, and so I know that you’re the best dating coach to get advice from. My boyfriend and I are both 24 years old, and we’ve been together for almost a year now. We get along really well and feel like our natural selves with one another. He has always treated me well, and is kind, helpful, hard-working, loving, and also has a backbone. I find him attractive too, and so, of course, I compliment him, but he always denies it. He tells me that he isn’t good looking or attractive, and I think he’s quite self-conscious. For instance, when we went to the pool, he swam with a top on, and other times he’ll make fun of himself. Is it common for men to feel this way? And is there anything that I can do or say to help make him feel better?


This is a question about insecurity. Nothing more. Nothing less.

So, why is your boyfriend insecure?

Because his Mom or Dad wasn’t supportive.
Because his Mom or Dad wasn’t available.
Because his Mom or Dad was critical or abusive.
Because he was teased throughout school.
Because he’s not a particularly charismatic individual.
Because he’s not particularly experienced with women.
Because he comes from a self-effacing family or culture.
Because he sees himself accurately and doesn’t have reason to be confident.
Because a bunch of the above explanations are true.

This is a question about insecurity. Nothing more. Nothing less.

I’m fishing here, but you get the idea.

There are any number of reasons why an individual will lead with his insecurities.

But all of them predate you and are probably pretty deep-seated.

Thus, there are only two cures for insecurity:

      – Therapy, which requires time, money, and a good recommendation.

– Experience, in which your boyfriend can learn that the negative things he’s internalized about himself are not entirely true, shouldn’t define him, and are dragging him down.

You can’t force him to go through therapy, but if you’re a great girlfriend, you can have this very conversation with him and ask him why he continually insults the man you love.

He doesn’t believe the good stuff yet. But with your help, he might — and you’ll have a more attractive and confident boyfriend when you’re done.

Then just sit back and listen. And, whenever possible, give him all the positive reinforcement he needs.

Soon, he’ll see why a woman like you continues to choose him above all others.

He doesn’t believe the good stuff yet. But with your help, he might — and you’ll have a more attractive and confident boyfriend when you’re done.

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  1. 1

    This is good advice.

    Relationships are about building up another, and helping each other be the best version of yourselves that you can be.

    It is not one person’s responsibility to help another, but it doesn’t hurt to help someone see the good things within and without that they themselves cannot see.

  2. 2

    As the letter is quite brief, it is, as Evan says, quite tough to tell whether he is self deprecating or has a problematic self-esteem. In the UK it is seen as politeness to respond to a compliment by denying/minimizing it.

    The letter reminded me of an ex boyfriend who once stated that he hated getting compliments as it reminded him that he was not able to be as positive about himself as the person who was giving him the compliment. Very sad, as he is one of the most amazing men I have ever met, yet no amount of external validation would ever be able to change his mind about himself.

    Only your boyfriend can work on getting more confindence, though a supportive girlfriend who has his best interests at heart sure is a bonus. Have you tried having a conversation about it? Citing an example where his brush off of an accomplishment seemed to be too forceful?

  3. 3

    I say it might be time to reconsider this relationship. He sounds depressed and I felt depressed reading the question. It should not be your job to help make him feel better about himself. What happens when you disagree with him? Do you hold back because you’re afraid you will crush him? No thanks

    1. 3.1
      Strangely Rational

      Insecurity over one’s appearance is not a defining characteristic of depression. It’s a common symptom, but by itself it’s not enough to indicate depression specifically. It could just as easily be anxiety, or BDD, or any number of things, or nothing diagnosable at all.

      Please do not lump every mentally/emotionally unhealthy attitude under “depression” as if it’s some catch-all illness that anyone who’s not feeling great about themselves must have. That’s a common misconception. And I’m not sure what insecurity over his appearance has to do with being crushed if someone disagrees with him. That’s not the same thing.

  4. 4
    Karmic Equation

    A self-deprecating sense of humor is not necessarily a sign of poor self-esteem. When women do it, yes, it usually is a sign of low self-esteem. However, when men do it (and depending on how they do it), oftentimes it’s a sign of being self-aware and open to criticism. My bff, who’s a guy, is very self-confident and will occasionally be self-deprecating as a way to communicate.


    Yes, when women wear tshirts to to swimming, it’s a sign of self-consciousness. It probably is to men as well. But I don’t think it means as much when men do it as when women do it. I don’t think you need to sweat this one.


    I would say as long as you make him feel valued and sexy and he’s himself around you, you don’t have to worry about how he deals with the world. You’re his gf, not his mom. Don’t mother him on this and trust that he knows what he’s doing.


    If he’s otherwise normal (has friends besides you, has a good job, seems generally content with his life), I think he’s just being a guy. But if he’s often sullen or sad, doesn’t laugh, well maybe there’s more going on underneath, but it might take a professional to help him resolve that. There’s not a whole lot a layman can do, except to put up with it or leave.

  5. 5

    @ Maree (the op)
    “I think he’s quite self-conscious…Is it common for men to feel this way?”
    I would say that it is yes, especially for men under the age of say 25, when many have yet to start making their mark in the world.
    However, many/most of us do our best to hide it — which often manifests itself through getting drunk/stoned/some other juvenile behavior.
    As Maree’s boyfriend is still relatively young (24) I would give him the benefit of the doubt and attribute much of his insecurity to immaturity: hopefully he will grow out of it in a few years.
    “And is there anything that I can do or say to help make him feel better?”
    Unfortunately I have a fairly fatalistic response to this: I don’t think anyone can deal with another person’s insecurity: they have to deal with it themselves. No matter what you say to try and make him feel better, ultimately he is the only one who can resolve it.
    So the real question Maree should ask is: “can I accept my boyfriend as he is — insecurity, warts and all — or should I move on?”
    Personally I find insecurity an unattractive quality and – not meaning to sound harsh – but I usually cut insecure people off pretty quickly: a huge part of being an adult is resolving one’s issues.
    I do agree with Evan that two ways to deal with insecurity are through therapy and experience. Another great way to deal with it — especially for men — is through achievement. So if he could set goals — whether they be professional, academic or personal – and apply dogged determination to achieve these goals his confidence should arise commensurately upon their completion.
    The op’s boyfriend’s issue seems to involve poor body image; therefore setting a diet/fitness goal/program might help him in this regard.  

  6. 6

    Great comments Tom.

    I immediately thought of ways that OP and her boyfriend could engage in some fun, physically and mentally challenging activities together that would boost their mental and physical prowess and confidence.   Training for a Warrior Dash? Learning to sail together?   Or volunteering together at Habitat?

    Suggesting an activity such as this would demonstrate OP’s commitment to their togetherness and would pay   dividends by increasing his confidence.

  7. 7

    Thanks Evan, and everyone else, for the responses 🙂

    I will talk to him about it and slowly try to get him to see that he’s a wonderful and attractive guy. Sorry if I wrote the question in a way that made out he’s really depressed, he isn’t 🙂 and he’s very supportive and encouring to me, compliments me, is very affectionate and an all-round decent guy (in other words, I think he’s pretty amazing) so he doesn’t try to drag me down at all or anything. So yeah, definitely not giving him up lol. I’ll also take what Josie said, and do more hobbies and fun things/activities together.

    xo Maree

    1. 7.1

      People who could be conceited but are not, sometimes are the keepers! It sounds like your guy has a lot of great qualities.

  8. 8

    Maree, for myself, I always deny compliments because if you have a certain level of attractiveness, then agreeing with someone calling you sexy or good looking is seen as hubris; and I know from personal experience that people try to find fault with attractive people, it makes the accusers feel better about themselves. Labeling an attractive man or woman as arrogant or  stuck-up, is usually the easiest way to accomplish this.

  9. 9

    Wow !!! This article remind me of the forum I did 8 years ago…

    This will help me to help a friend who’s never had a good woman . Who know I might be that woman at the end of this …laughing out loud here…


  10. 10

    Eh, my ex’s insecurities showed up as jealous, controlling behavior. I did my best to support him and reinforce his worthiness at a core level, but I just ended up neglected and abused. Sometimes this insecurity or shame is so deep that only years of therapy can help. I couldn’t fix him without compromising myself. I had to leave.

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