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.

Ready for Lasting Love?
Ready for Lasting Love?

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,