DWI: Dating While Insecure

Are you an insecure dater? Are you painfully insecure about your looks and body type? Lately, I have been looking back at old pictures of me when I was skinny. Back then I was confident, secure, and even a little cocky at certain moments. I was a Teflon Diva nothing you could say stuck to me. I would wear certain things without a conscious sometimes. My little pom-pom shorts and skirts that had them looking at my legs for days.


What happened to the pretty girl I used to be? She was confident in herself and truly loved who she was. Frankly, I put on weight and I do not feel as sexy as I used to. Lately, I feel unpretty I know it is sad and have become painfully insecure. When I wear something I am watching for my rolls trapping my body in girdles. Hiding everything I have so I can fit in.


When a guy approaches me that I find attractive self-doubt entrances me and leaves me wondering if I am worthy of him. I never question whether he is worthy of me. Back in the day I would not think twice I would think we both lucked up. Now don’t get me wrong insecurity has followed me all the days of my life. I was teased as a child because I did not look the part. I was awkward skinny, with glasses, and dressed different then everyone else. So me ever thinking I was pretty was nothing short of a miracle. At that point in my life in those pictures I was a new Mommy with a new Mommy glow. Once I became a mother being ugly was no longer an option.



Dating was so easy for me I would kiss and dismiss a man so quick I was not taking any bullshit. Why should I have to? I wish I could get that back now when I am out on a date I am telling too much and wondering why I don’t get asked out on a second date. Or, I will jump the gun and get pushed into the friend zone and have a friend with benefits situation where my needs get denied. It is like now that I have gained weight I started settling for being a FWB (friend with benefits). I am tired of it. Plain sick of it and don’t get me started on sex. I feel like a whale climbing a tree sometimes. I have even lowered my dating standards. I gained weight and lost me.


I want to lose weight not necessarily to be skinny again but just so I get that sexy girl back. The girl who didn’t think twice about what a guy thought. He just better hope he gets a call back. I have a stone of confidence with a picture of me behind it when I was much smaller. I miss her so much. I have contemplated taking the picture down. It can be rather depressing. Yet some days it is a motivator for me. I will lose weight but it will be on my terms. It will be because I want to feel good about myself again. As I write this tears fall because it cuts just that deep for me. I want to learn to love again. The person I want to love is me. I keep saying the woman I want my daughter to be I have to be.


Too many of us are cloaked in insecurity. It has become a security blanket for us. Oh I will take this shit off of him because look at me I cannot do any better than him. True story I met a guy back when I was skinny and we date carefree no questions we hooked up when I wanted to and that was that. I wouldn’t take any shit off of him. One day before sex he said to me you are gaining weight you need to workout. I was floored and in complete disbelief did he just call me fat. After a while I became self-conscious and hated being naked around him hid the mirrors during sex just so I wouldn’t have to look at me anymore. My body was no longer beautiful; the masterpiece lost its luster.


Now I don’t want your sympathy but I do want to know when you gain pounds do you lose you. I was to be re-introduced to that sexier side of me. I love who she is I want to be her again. Confidence is something I long for; I want it to be where you can tell me nothing. Are you feeling like you gained weight and lost your sex appeal speak on it? Men do you mind a little weight or does the sexiness go out the window when the pounds come on?



Speak on it. Leave your comments below.


One thought on “DWI: Dating While Insecure

  1. I think the key is having self love and self esteem. Everybody body is going to change as they get older thats just a fact of nature. You still have to find the beaty within yourself. If you don’t I doubt anyone else will. Wakling around feeling you are ugly and insecure hovers over you like a cloud and some men are real good at picking up on it and taking advantage of it. Hence leading to those poor relationship you were talking about, some men prey on weak women. If you come across that way, that is how you are going to be treated.

    For more relationship tips and advice check out –>http://www.romance101.net

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