Women Dating Over 40: What’s Up With the Bad Body Image?

women dating over 40

By Jackie Pilossoph, Editor-in-chief, Divorced Girl Smiling, Love Essentially columnist and author

This is a TRUE story that I think will help countless single or divorced women dating over 40. It has to do with getting older, body image, self-love, self-esteem, and my girlfriend who needs a good kick in the ass!

Last week, she and I got invited to go on our friend’s boat. So she asks me, “What are you going to wear?” and I say, “a bikini, jean shorts and a tank top, but I probably won’t take off the jean shorts.”

She then goes into this whole rant about how she doesn’t want to wear a bathing suit, blah blah blah, she feels old and doesn’t like her body. Now, if you saw this woman, you would not believe she was talking like she was. You’d have thought she was 50 pounds overweight. My friend is so beautiful (which is why she needs a kick in the ass.) And, sadly, she is not alone. Why are women over 40 so tough on themselves when it comes to our bodies??!!

I told my girlfriend the story I am about to share here. It involves a guy friend of mine who went out with a woman he met on a dating site. He described the woman as really, really cute and nice and said they hit it off and went out a few times.




One night, they started to kiss and clothes started to come off. He said he got a sense that the woman hadn’t had sex in a really long time, but that it was OK and he was looking forward to making her feel relaxed and at ease and happy. As he undressed her, she got more and more uncomfortable and awkward. She said to him, “I was hoping to lose 10 pounds before I had sex with someone.”

He answered, “I think you are really beautiful. Just enjoy yourself.”

The awkwardness and ill at ease attitude continued, and he didn’t really tell me if they ended up sleeping together or not. What he did say was that her insecurity was a huge turn off, and that the girl really was pretty, and that he had a hard time understanding how she could have such a bad body image. He said she could have stood to lose a few pounds but didn’t care at all. He said that he himself could lose a few, and that he liked her just the way she was. But because she was so insecure, she became unattractive to him and he lost interest.


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Now, shouldn’t that be a valuable lesson to all women dating over 40 about  what men really think? I’ve heard over and over again from men how much they love a confident woman. Make no mistake, what she looks like definitely matters to an extent, but how she feels about herself matters so much more.

It is that happy, self-assured attitude and poised confidence that can make a middle aged woman look more beautiful than any movie star. Men have told me that attitude and personality causes them to fall in love.

Wake up ladies!! Women dating over 40, just be yourself. Look in the mirror and instead of saying, “I hope I look OK,” say, “Am I happy with the way I look?” If the answer is yes, nothing else matters, and if your date doesn’t find you attractive, you won’t even care! If the answer is no, then figure out why.


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Is the problem emotional? Are you too hard on yourself? Does the problem stem from an ultra-critical ex who made you feel awful about yourself for years? The key is recognizing it.

Is the problem that you truly don’t like your body? If that’s the case, then it’s up to you to make changes. Whether that means losing weight or gaining weight. But I want to stress something. Weight should not be anyone’s priority, in my opinion.

The priority should be two things: being healthy and feeling good.

An optimal weight should be a byproduct of eating healthy, staying physically active, exercising your mind, being social and living your passion. These are the things that keep you physically and emotionally healthy and happy.

I have lived most of my life worrying about my body, how it wasn’t good enough, skinny enough, fit enough or pretty enough. I so regret that. I can honestly say, when I hit 50 and stopped caring so much about weight, and just focused on being healthy and feeling good, I became the happiest about my body that I’ve ever been. It’s really a feeling of peace. Give that to yourself. You deserve it!


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Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorce is a journey. Live it with grace, courage and gratitude. Peace and joy are on the way! Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling. The author of the novels, Divorced Girl Smiling and Free Gift With Purchase, Pilossoph also writes the weekly dating and relationships advice column, “Love Essentially”, published in the Chicago Tribune Pioneer Press and the Chicago Tribune online. Additionally, she is a Huffington Post contributor. Pilossoph holds a Masters degree in journalism from Boston University.

7 Responses to “Women Dating Over 40: What’s Up With the Bad Body Image?”

  1. Kristin

    You are my new hero! I’m so loving reading all of your blog posts and your article in the Post today, was exactly what I needed. It’s so hard being in a divorce, but even harder pill to swallow when I pay him child support ! The worst…but I have to just kick myself in the ass and know that I AM the confident, businesswoman and he’s not!

  2. Sheila

    Thank you, Jackie. I’m 44 and in the midst of body image hell. I quit smoking (which I’m really proud of), but I’ve begun gaining weight for the first time in a lonnnng time. Your article is very, very helpful. I hope to get there!

  3. Suzanne

    This is crap. I SUFFER, I REALLY suffer from body image Issues since turning 40 and your advice is “cut it out”? I guarantee that you helped no one with a REAL problem with this shaming crap. Society bombards us with images that make us feel valueless and jokes that boast being with a 23 year old is the ultimate prize and that the 44 year old wife is gross in some way. The women in you story is suffering and that is used as the reason she is less attractive, so is she pretend and suffer in silence? Thanks for simplifying something that causes so much suffering and is so complex.


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