I Have A Lot Of Baggage And Low Self-Esteem. How Can I Stop Accepting The Wrong Men In My Life?



I read your book: “Why You’re Still Single” (among many, many other single self-help books,) and I’m here because I trust your opinion. You say it like it is, not what wants to be heard. And that’s important. My question comes with a bit of back story. I am a 23 year old college graduate who has been single my entire life.No boyfriends, no serious relationships. Just dates and casual relationships. I have a lot of baggage and emotional torment that keeps me from opening up to men completely, you know, the classic ‘daddy issues’ and other various insecurities, including body image. I am 5’9″ and over 250 lbs. You wouldn’t guess that if you saw me!   But I’m not a supermodel (that’s perfectly clear and I’m not making any excuses.) I’m a curvy girl. Pretty face, nice smile, good personality. But imperfect. Aren’t we all? I am well aware that I am damaged and need a little repair before I can find a healthy relationship that is good and that lasts. I’m working on it slowly, attempting to build my self-esteem and self-confidence enough so that I get to the point where I can go out into the dating world unafraid of what I have to offer. I’m a chronic offender of settling for a sexual relationship to make myself feel ‘wanted’ and also of accepting the wrong men (great advice, by the way) because I feel that is the only way I can get men to really want me. It’s horrible and I hate this mindset. I’m resolved to change. Therefore, my question for you is: What can or should I do to build up my confidence and feel secure and attractive when I approach men? How can I start believing that I am worth more than I give away? I want so badly to respect myself so that men will respect me, but I’ve started off with such bad habits and I’m having trouble breaking them. I hope you can help me, or that you can point in the direction of past articles that will give me some clarity and empowerment. Thank you! — Heather

Dear Heather,

Thank you very much for trusting my opinion. Sincerely. I’m honored.

Yet I must remind you that I’m not a psychologist   — just a guy who’s been on two million dates and has spent an inordinate about of time talking about them.

That said, apart from the obvious fact that you need “real” therapy, not “internet blog therapy,” there are some things that you can do to break your bad habits NOW.

As I see it, you’re in the middle of a vicious cycle.

Baggage. Emotional Torment. Body Issues. Daddy issues. Sex issues. Insecurities.

You have to make a choice to no longer tolerate bad behavior on the part of men.

You’re not necessarily responsible for how you got there; you are responsible for how you stop it. Just as a smoker is responsible for stopping smoking, despite the physical and emotional addiction to the process, you have to make a choice to no longer tolerate bad behavior on the part of men.

This is not easy, but it’s the easiest thing you have to do.

After all, you have an idea of what proper behavior is — but due to your shaky self-esteem and your past, you end up accepting far less, just to have SOMEONE.

No longer.

Guy texts you once every two weeks for a booty call? Delete his number.

Guy doesn’t want to take you out for dinner, introduce you to his friends, call you his girlfriend? Cut him loose.

Guy tells you that you’re obese or an emotional basket case? Dump him.

Will you end up getting rid of pretty much every guy in your life? Yep.

Will you be losing anything? Nope. The only thing you lose is the toxic energy that you’ve allowed to swirl around you for so many years.

Start surrounding yourself by good people. You are the company you keep.

Next, start surrounding yourself by good people. Kind women. Ones with healthy self-esteem, solid jobs, and positive relationships. That’s one of the hardest parts of being in your early 20’s — everyone’s so screwed up and finding themselves, there are few role models to be found.

Find them anyway.

You are the company you keep. Surround yourself with slackers, or druggies, or people with any sort of self-destructive tendencies, it will be doubly hard to raise yourself from that morass. You need to mirror the behaviors of good decision-makers with high self-esteem in order to break your cycle. It does not come naturally.

If you do this, you will have taken care of the external by minimizing your interaction with bad men and bad friends. Now you’re just left with yourself. And that’s going to take a lot more work.

It’s going to take therapy to excavate and reconcile your childhood issues.

It’s going to take weight loss — not just for its obvious effects on your dating, but for your health and self-esteem as well.

And it’s going to take a lot of practice. After all…

Practice breeds success. The more you do something, the better you get at it.

Success breeds confidence. The better your results, the more you’ll believe in yourself.

Confidence breeds success. The more you believe in yourself, the better your results.

Giving up bad guys is as simple as refusing to be treated poorly.

This goes for women with serious relationship issues. This goes for shy people with no confidence in talking to others. This goes for those who are sexually inexperienced.

The more you do something, the better you get at it.

The better you get at it, the more confident you get at it.

The more confident you get at it, the more success you’ll have at it.

This is your vicious cycle in reverse. This is the positive cycle.

I can’t tell you where to begin, but I can tell you when to begin.


Giving up bad guys is as simple as refusing to be treated poorly.

Start there, watch your confidence grow, and please come back to let me know how it’s going.

Good luck. Much love,


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  1. 1

    “Overcoming The Rating Game” by Paul Hauck might be useful book for you ( http://tinyurl.com/3a9x9bg ). Hauck believes that seeking higher self esteem is a bad idea.
    Yes, you read that right.     Trying to get higher self esteem is a bad idea.
    Self Esteem is based on qualities that can change….meaning your self esteem can come right back down again.    You may decide you are a good person because you are good looking, a hard worker or do well at your job.     You can lose your looks or you can have a crisis in your life that makes you screw up and lose your job.     How are you going to rate yourself then?
    Hauck teaches people self acceptance rather than self esteem.   To feel good about themselves no matter what circumstances they find themselves in.

  2. 2

    Heather, you’re a good person regardless.   But here’s what I have to tell you….get yourself a bodybugg (Apex.com), wear it every day, follow a fitness & weightloss program.   Losing weight will change the way men treat you…just a fact of life…you don’t have to like it, but that’s the way it is.   Then hold yourself and men up to a  a high standard.   As others start to see you differently, you will start to believe and see  yourself differently.   Let that become your reality.   Men that used to not give me a second glance on Match are now clammering to meet me.   I’m still the same person, but my options have changed.   Feels great, too !

    1. 2.1

      I’m all about encouraging Heather to make healthier choices but it needs to come from the motivation to do this for herself- to live a healthy and long life, with a positive self image , not to make the men of Match “clamor” to meet her.

      The fact is, if Heather does not heal her self image and psychological wounds, she will make poor choices in dating , even if she becomes thin and conventionally pretty.    98 percent of the men who sought me in my hotter 20 something years were the player type shallow guys who would have made poor long term partners.

      I strongly recommend Heather avail herself of counseling and support groups that can truly help her grow healthy and mentally strong.



    2. 2.2

      Interesting, but I have to say I’m “average” sized and decent looking and men have treated me like crap.   Hell, Halle Berry has got the best romantic history ever! NOT.

      Meanwhile, I do have overweight friends in good relationships.

      So, while losing weight is good overall I think she needs to spend just as much time on the inner work.

      She’s young now, but for any number of reasons the weight could come back and it would suck to be with someone who only valued her for what she offers physically or if she built her entire esteem on her weight loss.


  3. 3

    it took my years to get to where you are now – consider yourself way ahead of the game that you realize you are not happy with your choices, and remember that you are never any younger than you are at this very moment.   The world is your oyster; pick your pearl. You sound like a very smart girl, get healthy, exercise,  eat well (what you put it is what you get outward also), work on getting your head clear, and continue  reading blogs like this, as well as  any postive, helpful books you can – as EMK said – practice…practice..practice til it becomes a habit.   Good luck.   I have a feeling you will be just fine 🙂

  4. 4

    @Donna post #2
    I never heard of the bodybugg before your post.   Interesting!
    I also used calorie counting to lose a large amount of weight a few years ago, though I used a free system ( http://www.fourmilab.ch/hackdiet/ ).     I got by with a pen,   a drugstore notebook, a good scale and nutritiondata.com.
    I agree with you, nobody has to like it, but you do get treated differently when your looks improve.

  5. 5

    Heather, the very first thought that is crossing my mind is that you need to learn how to love yourself first ~ wholly, completely and unconditionally; others [unruly men, friends, co-workers, etc.] cannot truly give you the love you need to believe you deserve [that is a key word, deserve] and can then give to yourself. While the changes that Evan wrote about are good ones for sure, and your self-awareness is to be applauded, just like a smoker who struggles to quit and never seems to quite make it last, you will struggle and may continue to repeat your behaviors until something much deeper changes for you on the inside. This will not happen overnight.
    A program I recommend is “Inner Bonding.” You can find it on the web.
    In the meantime, work toward learning how to be stronger and stop reaching out to the men in your life to fill the empty void you feel. Their responses only make you feel more empty anyway. Love works from the inside out, and then from the outside in. 🙂

  6. 6

    Dear Heather,
    Your story sounds much like mine with one difference, I MARRIED one of the destructive people I was so attracted to. Needless to say the marriage was a disaster, with us both bringing each other down and dragging the other back into the muck when either of us tried to get healthy.
    Fortunately she realized being together was toxic to both of us and divorced me. INCREDIBLY PAINFUL because it reenforced   all my negative feelings, I realized I was willing to do ANYTHING not to go through that again.
    I don’t know if your baggage is heavy enough to see a counselor, but in my case, I went to the couples counselor we’d been seeing. We spent a year undiong the damage froom growing up in an abusive and alchoholic household.

  7. 7

    Roger continued…(be careful where you hit enter, my above reply is totally unedited.)
    Much as Evan advised, My counselor gave me what I thought was the most amazing advice, I think it is perfect for you.
    It is OK to hold out for a person who is genuinely good to you. One who values you for who you are. One who doesn’t put you down. Less than that is continuing to invest in your own unhappiness.
    I thought this to   be impossible, Yet shortly after that meeting, I met a woman who was all those things and we eventually got married, raised a couple of kids and spent 28 years together.
    I can’t guarantee the marriage part, but I can say that if you dump much of your own baggage and spend time with people who are genuinely good to you, the quality of your relationships will skyrocket.

  8. 8

    Heather, as someone who is still working through some issues, including struggling with weight, it is a process.   Be patient with the process and be patient with yourself because it took a lot of years of toxicity to get where you are currently at.   The change won’t happen overnight and change and growth are painful.   They require sacrifice, but when that becomes LESS painful than staying the same, then you will gain momentum.  

    Evan is certainly correct in surrounding yourself with SAFE quality people who accept you unconditionally.   While you are in the process of growth, that is what you need.   Those are the people that will support and encourage you when it gets tough and you want to quit because believe me, you will.   The old patterns are easy and familiar, even if unhealthy.   If faith is something that is important to you, plug into a good church.   If not, maybe you can find a support group.   Weight Watchers, Weigh Down, or TOPS are good places to get support.   There might be support groups that deal with the emotional issues you wrestle with.   You might even examine if you need more intensive one-on-one counseling.

    Realize that you are person of worth or value no matter what your size.   I can understand the frustration of being treated differently when losing weight, because that reality is part of what has really kept me from being successful at it.   If possible, try not to view it as losing weight to get a date, but because you want to be a healthy person who cuts the risk of disease and illness by controlling what you can.  

    It’s also important to realize that even being overweight doesn’t mean putting up with lousy behavior from jerky guys.   You are like every other human being who has the basic right of being treated with dignity and respect and those who cannot give you that have no place in your life.

    Finally I would say follow your bliss; do those things that bring you fulfillment and joy and don’t seek permission or approval to do so.   Learn how to meet your needs and care for yourself.   When you have a good support system and circle of friends and family who love you unconditionally, and you have a life full of goals, ambitions, and fulfillment, you’ll be amazed how unattractive those jerks become.  

    I wish you love and all the best on your new journey!

  9. 9

    I think  one of  the most painful, however, MOST helpful actions I ever took on my journey (because it is a journey, and we are all on it) of becoming  a healthier, happier person,  was cutting loose the toxic people in my life. For me that included my family.   It was a very difficult and painful decision and adjustment, but it was absolutely the best thing I could have done.
    Surrounding yourself with people who have what you want and can serve as a model of how to get it really help to improve your direction, at least it did for me!
    Its hard, but you’ll make it.   Good luck! 🙂

  10. 10

    Spot on Evan.

    Heather, its great that you’re recognising this in yourself at your age.   I’m 45 and  am working on childhood stuff that gets in the way of me having fulfilling relationships.   I agree with Evan that therapy is usually in integral key to making significant changes like this and suggest you read up on schema therapy as its designed to tackle these deep seated patterns that come from our childhood experiences.

    Good luck and keep persisting.   This stuff takes  a lot of effort and the benefits don’t necessarily come quickly but know that you are worth it.

  11. 11

    Not many comments for a change. No surprise as Evan’s advice here is spot on.
    Heather, I recommend the bulletin board Low Carb Friends for great support for weight loss and almost anything else. You don’t have to do low carb to be welcome and people hang around for years after losing weight because of the friendships. Plus, maintaining is also hard work. Best of luck to you!

  12. 12

    Some of the people here have said you need unconditional self acceptance before changing yourself. And i agree. Because you can get back to not being confident after a therapy too if you dont accept and love yourself with your flaws.
    And then you get rid of your flaws. Its much better that way. You said it! No one is perfect. So why should you beat yourself up about having flaws. Don’t lose your cofidence over your set backs.

  13. 13
    Jason Miller

    Dear Young Heather,
    All the advice here is really good.   Two concepts stand out for me reading your email:

    You’re basing your happiness on external validation.   That’s what we all did in our 20’s.   You’re just finishing college and starting out in the world.   It’s only natural for you be this way.   You seek approval when you apply for jobs.   And you seek approval when you date guys.   This can be just a phase if you start working on it now.
    Anything you do to improve, learn, or challenge yourself now will help you feel better about yourself from WITHIN!   Self esteem and confidence come with just plain surviving challenges, not just succeeding outright.   You don’t always need to succeed to learn.   Just remember you will survive and see the outcome no matter what.
    I don’t want to tell you what to do, but my intuition tells me you’ve got a competitive streak.   If that’s true, leverage it to your advantage.   Do you play sports or have any desire to?   Good way to get fit, have fun, and be part of a supportive team.   Or maybe you want to compete in another way.   There is an outlet for you to develop and transform yourself APART from dating and men.   Start trying things you think you might enjoy.
    As for your body, lots of guys like tall and curvy.   You just don’t believe it yet.   Start extending the period of time between first date and sex.   Delay it as long as you can just to see what guys do.   It’s gonna be hard because you’ll be afraid he’ll run.   Test yourself and see what happens.

  14. 14

    Working on yourself, LOVING YOURSELF, valuing Yourself 1st is of Vital IMPORTANCE.   As you HAVE to ACCEPT YOURSELF as You are at this moment in time, regardless because YOU are the FOUNDATION to the beginning of any other relationship you may pursue be it a friendship, a love relationship, or a combination of the 2.   Pursue things that TRULY INTEREST you and speaks to your heart.   It will be natural and spontaneous to seek like minded and hearted people if you do those things.   Join a group such as animal rescue if that speaks to your heart.   Follow your BLISS, pursue your education of what you interests you. Because until you are Happier with yourself, then you can’t be present in a loving relationship.   Do what you need to improve and work on yourself and value WHO YOU ARE, and don’t even CONSIDER BEING with someone That DOES’NT DO THE SAME, BECAUSE EACH AND EVERY ONE OF US, “DESRVES TO BE LOVED” for who they are, not Who you would like to be as we are ALL WORKS IN PROGRESS.   IMPERFECT yet willing to work on our imperfections.  

  15. 15

    First off to Heather – I want to say congratulations on seeking help and for IDENTIFYING your problems.   As a couple of readers mentioned above, not everyone is willing to admit their issues which may stop them from having a fulfilling relationship/s.   I admire your courage to reach out and I want to encourage you that you have now taken the first step towards a more positive and healthy future.   It is a journey and Evan is spot on in advising you to surround yourself with emotionally healthy people.   Only then you will be able to adopt better ways for sabotaging your path to a more successful future.
    Secondly, Evan, you are a gem!   You are so sensitive and sweet towards her without losing your honesty and integrity in your advice to her.
    I know this blog is “old”.   I just came across it and felt compelled to respond.   Would love to know her update, if any.

  16. 16

    Perfect answer Evan.   Sift out the bad ones and eventually you’ll get to the good ones.
    And in the meantime, at least the bad ones aren’t making you feel worse about yourself.
    Bad company breeds bad habits and bad attitudes.

  17. 17

    Hi, would guys consider,   telling them you are being in between jobs and that a parent is fighting cancer baggage?   Because I don’t know if I messed up with this one guy because of that.

    1. 17.1

      @Sarah: Some pple might say don’t tell so soon, but I personally think it’s fine to tell about job problems or even family issues. How can u not tell a date if it’s smthg so major anyway? For example, I tell even before the first date that I’ve gone back to college part-time and can only work part-time as a result.
      I think the parent fighting cancer is something u can wait a few dates to tell, because it’s not really part of your own personal life, but if you’re feeling regret because u think u screwed things up with a guy by telling him these things, I don’t think u did. A guy who really wanted to be with u would not be deterred by these 2 things. I think u could continue telling guys this, as long as u don’t sound really depressed about it. =) Most pple don’t want to hang out with someone who’s depressed on every date. I talk about some issues on my life when I’m on dates, but I balance the conversation with light happy stuff too.

  18. 18

    Heather, I am so happy you are willing to tackle the beliefs that are holding you back in life. When i was in my 20s i struggled my some of the issues that you have mentioned and the following solutions really helped. Maybe some of these points   that helped me might help you.

    – I decided to have zero tolerance for booty calls/casual relationships. I enjoyed casual sex (The Oxytocin never seemed to grab hold of me) and most of the guys I was with were really nice men who never intended to hurt me. The only problem is that a purely sexual relationship is the easy way out. The men (even the ones who might be interested in more than sexytimes) never come near enough to you to be able to form a genuine emotional bond and you never have to work on breaking down your barriers so that you can let someone in and see you at your most authentic and vulnerable self. Saying no to booty calls is not only about weeding out the wrong men, it’s also about challenging yourself to give time to the nice guys and getting to know them as a whole package, at the same time letting them get to know you. Scary, but in the long term far more satisfying than a series of band aid flings.

    – Only good people get to be your friend.   Friends you can laugh with, who are optimistic, kind, caring, giving. Friends who see the world as a beautiful, if flawed, place, rather than a source of bitterness. Are there any meetups in the area you live? A local drama group or book club, any kind of gathering that comes together with an interest of yours? Now that you have expelled all the leeches in your life, its time to do some fun stuff   (there is more to life than introspection, however important that may be) and meet people who are worthy of your time. I joined a drama group when I was done with my old fair-weather friends and met people i am still close to ten years down the road, who are truly priceless.

    – You will only ever have one father. I do not know anything about your history with him, but it sounds as if you need a good therapist that will assist you with closure. If you can get to the point where you can forgive his shortcomings, you will free up so much energy that can go into living a full life.

    – Women in modern society can be held up to ridiculous standards when it comes to the way they look. I used to work as a model and an actress and that gave me a lifelong antipathy to constantly being told that cookie cutter beauty was the highest goal a woman can attain. By all means, do make healthy choices and strive towards the best possible you. But you don’t need to look like a model, in order to have a happy life. Being strong, in good health and happy in your own skin is a realistic goal, and will bring you much farther.

    You are in your early 20s, and have written a very thoughtful and self aware post, I am in awe of you! Good luck on your journey.

  19. 19

    Evan- you might not be a trained shrink but your advice is better than what most of them give out.   I just forwarded this to my daughters.   Thanks.

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