Dating a Younger Guy: How Can I Overcome Body Insecurity and Fear of Intimacy?

Question

I’m a 39-year-old single mom who recently started dating a guy who's 14 years younger than me. Initially, I was drawn to him mostly because of his physical attractiveness, but as we spent more time together, I developed strong feelings for him. Our connection feels profound, and we get along incredibly well. He’s adventurous and energetic, which matches my own high energy, and our maturity levels seem more aligned than with previous partners my age.

We haven't been physically intimate yet, but Im scared to move to that part of our relationship. It's not that I don't want to be physically intimate with him (I want to super badly!). However, Im really worried/insecure about getting naked in front of him. He's got a young/fit body that's super attractive (and will look amazing naked). While I do keep my self in really good shape, I still have the body of an almost 40 year old woman who has had 2 kids. I'm just so scared that when I get the courage to take off my clothes he'll look at my older body with all my stretch marks, get disappointed/turned off, and think 'I could do better than her. There are plenty of younger/hotter women who'd be with me'.

Additionally, my ex-husband (who is older than me) left me for a much younger woman. That's adding a lot to my fears and self concerns (especially since my boyfriend is younger)

With that being said, my boyfriend often expresses a high level of attraction and desire to be intimate with me. However, I just get scared that what he's thinking in his head isn't the same as what he'll see when we get intimate, and he'll get disappointed after he sees me (and maybe leave me for a younger woman)

How can I get over being so self conscious about my body, and not be worried about being intimate with my boyfriend?

Updates

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Also, I feel kind of silly for feeling this way. I'm an established middle aged woman. Feeling insecure about my body and what my (much younger) boyfriend will think makes me feel like I'm being silly/ridiculous. However, it's where I am.

Realistic07 · Accepted Answer

So you should know that your concern is valid you are 39 and he is 25. Logically there’s room for worry.

A few things to note:

Firstly, he is 25 at that age. He still figuring out how to make his life what he wants it to be.

Secondly, what are his thoughts on children and being a young father? Logically marriage is something to be considered. With children that’s a big consideration.

Thirdly as you grow older there’s going to come a time where you need to be taken care of more, and you’ll be 53 while he is 39 in 14 more years. Between that he may want to have a child of his own biologically his own. In addition what happens to the potential of his life?

Fourthly does how he make you feel justify what kind of life will come of it? How will you explain your relationship to your children because they will ask? How will that affect their lives for the better and for the worst?

With all of these questions comes a certain amount of seriousness, and reality. One thing would be if it’s just a fling, but the way you’re hinting at it makes it seem like more than that. So these questions become an ever present reality. Should these things scare you? Yes; because if your relationship goes wrong, it’s not just you that suffers. It’s your children and him as well.

So now that we’ve gotten through the scary reality part, let’s dive into the you part that says you’ve weighed all of these questions, and you still want to be in the relationship. Well, now it’s pretty heavy after that series of questions isn’t it, but let’s digress for a bit.

You’re with him currently you know you want to continue being with him, and you even want to rock his world. Your insecurities about your body I understand that they come from a real place. Plus your ex-husband is an jerk. It’s unfortunate, but it’s true.

So that brings us to the way you view yourself I want you to understand if he is this interested in you how you look is not a concern. That boy has mentally undressed you hundreds of thousands of times at this point. So don’t worry about being intimate with him.

Now I understand that he makes you feel good about yourself like your desired & wanted, lusted after, he makes you feel youthful in heart & spirit. Which is a wonderful feeling mind you, but you only feel that way because somebody is treating you the way you wish you could’ve been treated.

Something to note anyone who isn’t a complete jerk would have made you feel that way. It’s good that you’re being treated well, and don’t get me wrong you do deserve to be treated well.

That said we have to weigh the scale. Are you treating him well knowing the realities of what I’ve asked you?

It doesn’t take much to have sex with someone or even just to be in a relationship. All said, carrying a relationship is far different than just being in one. Two peoples devout commitment to one another to be there when the going gets tough, and to handle the problem as they come together.

Everything said and ironically enough i think how you look is probably the very last/ least thing on the list to worry about. Is it impossible to have this relationship? No. Will it take extreme effort, and sacrifice? Yeah. Will one of you sacrifice more than the other? Most likely.

As long as those realities can be respected, then there’s always hope. So go try and make the relationship worth having. Also go rock that kids world not only do you want to, but he’s very willing. As for the relationship, who knows I suggest try and make things work, and the best thing y’all can do for one another is try to be realistic with one another.

Well, that’s my opinion in this for better or worse. I do wish you both luck.

Lliam · Accepted Answer

A lot of people have some degree of body insecurity. We are super critical of ourselves and get carried away worrying about perceived flaws that others might not care about or even notice.

What is perfection anyway? Beauty is in the eye of the beholder.

It does no good to worry about such things. You have two choices: Get physical or not.
If you don't, you will surely lose him. If you do, you might lose him and its no worse than the first option. But you might find out that he adores your body, especially if you know how to rock his world. And if he really likes you as a person, he will be less inclined to be critical about any physical flaws.

One of my girlfriends had insecurities. She was 30 and I was 36 and in really good shape when we met.
We wound up living together for almost two years. I loved her with my heart and soul. Physically, she was my idea of the feminine ideal, and I liked everything else about her.

The first time we had sex, I sensed a bit of insecurity when she undressed. But that made her undress slowly and reveal herself bit by bit in a way that I found super sensual. And her vulnerability turned me on. Then she proceeded to rock my world. It was the most sensual experience of my life.

She always wore heels. I thought they must get uncomfortable, so one time I asked her why. She said she thought her legs looked funny without them. Well, she had the most adorable, perfectly sculpted legs. But she was 5'1" and I'm sure she was insecure about her height.
She was also concerned that her boobs and butt weren't as tight as they were when she was younger.
I thought her boobs and figure were perfect.
One time she commented "You used to be able to bounce a quarter off of my ass." That told me that she was insecure. But, OMG, her ass amazing! It was a woman's ass.
Her tummy was flat when she was standing, but she did have some fat that was apparent when naked. I loved that soft padding.
Everything about her was gorgeous. Plus, the sex was the best I had ever experienced in my life, and I had had girlfriends since I was 16.

I learned immediately that she was hypersexual and orgasmic. Her body was erogenous.
I had insecurities of my own but ignored them. The main one was feeling slightly inadequate about my 5 3/4" dick. But, even though we both worked full time, we had sex at least 2 or 3 times a day, and often for hours at a time without a break.
She made me feel like a sexual god.

So, my point is, don't worry about your own insecurities. Let your partner decide. You really have nothing to lose.
You can't be platonic friends forever.

TheRealPepperPotts · Accepted Answer

Here's my thoughts: What if you took it slowly and gauged his reaction with some teases? For example:

Go to the pool with him, and wear a great swimsuit. Observe his response.

The next time, do a bikini that fits you great with a coverup.

Wear some short shorts and a tucked-in, loose t-shirt with no bra when you know he's coming by.

Do a date night with a slip dress and some slow-dancing when you are ready to go for it. With the build-up, hint that you forgot undergarments tonight...

You can gradually build up to it, and keep an eye on his reactions. If he seems avoidant, no loss of dignity for you or awkward moment. But I suspect it will be just fine.

Anonymous · Accepted Answer

Just own it. Act like you’re the godess you are and even if you don’t feel confident and secure in your own body act like you do. Put on your best show and fake it until you make it. There are few things as attractive and sexy as someone being (or at least convincingly seeming) confident in their own skin no matter what they look like. It can make an average looking person attractive. And obviously with a 14 year age gap this guy likes older women. He could have someone his own age if he wanted to but he doesn’t. Also remember that we are our own worst critics. Things you’re insecure about he may not even notice or think twice about.

ohsheeT · Answer

What is the serenity prayer I don't know how it goes but if you know what it is to accept the things I cannot change or something like that.

First of all he's with you because he wants to be with you second of all it's not so much about your body it's who and who is inside the body... It starts from the heart goes to the wisdom the smarts The compassion the passion the confidence on who she is if you get in bed with him and you start thinking about your body and you start touching or making love you're not going to allow yourself to be the best you can be and that's what you have to do so it is what it is he's with you because he wants to be don't worry about the future because it's not here only worry about today this moment yesterday is gone if you want to tone your body up really fast drink lots of water fruits and vegetables because that hydrates you walk 30 minutes a day at a very fast pace and I guarantee it within 2 weeks your body will start toning up within 4 weeks you will see such a major difference every part of your body will tone when you get out of the shower run rub lotions on your body to moisturize the skin and it will also take away stretch marks he's not too worried about that he likes you for who you are on the inside the outside is just next to bonus you just better make his day when you get in bed except for don't be too aggressive guys like to control LOL. Just be in the moment and do it you feel you need to do don't try to be anybody else don't try to hide anything don't put yourself down just being that moment

MrOracle · Answer

Most men have an uncanny ability to mentally undress women and have a pretty good idea of what they look like. And while there are some shallow jerks in the world, most men are not, and most men who would date a 40 year old mom have a pretty good idea of what comes with that package. I won't say it's impossible, but you are at least UNLIKELY to surprise him.

Besides, there's nothing you can do to change it, and if it's a problem for him, the sooner you find out, the better off you are. The further down the road you kick this can, the more it will hurt if it's bad news - and the more precious time wasted if it's good news.

molonski2 · Answer

He doesn't need a girlfriend , he needs a mother , that's completely ridiculous combination , now let the boy grow up , take responsibility and find a girl younger than himself , and finish it immediately , otherwise it will just be pure heartbreak for you , no matter how insecure this boy is , he will eventually wake up and you are just FAR too old for him , be realistic and wake up , this is guaranteed heartbreak and pain for yourself , honestly just don't be so dam stupid , this is utterly obvious.

Oncewildtwiceburned · Answer

As I read your story I literally thought you were my girlfriend, she’s in her 40s and I look fit and strong for any age.

I am begging you to not start sleeping with him you don’t want the heart break. Its going to be tough for not only you but maybe your kids. He might want kids someday, its going to be awkward before it gets tough. If he is a looker he could continue to be a looker until 50 meanwhile his savings account grows. It will likely be tough for both of you. My heart kind of sank as I reflected my own predicament. I feel like such an asshole approaching an inevitable breakup, hearts and feelings will be hurt and I don’t like that. Its not the end of the world but its going to feel like it for someone and the guilt will be heavy on my soul, so much so that I don’t know what to do. Just rip off the bandaid before you get more cuts.

morganherrel · Answer

You're afraid of what you don't know, and it's a thing you have to learn eventually, right?

So instead of being anxious, be curious to find out what happens!

Channel the nervousness into excitement! When he tells you that he loves what he sees, it will be that much more rewarding.

That said, if you're wondering what you can actually do to change the outcome while improving confidence, then an austere diet and fitness routine would be very helpful

But based on what I'm reading in your post, I don't think that's necessary (:

He likes you! Good luck!

ICanSmellTheCosmos · Answer

It's alright to be insecure. That worry will be there until the day you die. Part of being human.

For what it's worth, half of my male coworkers wound up with older wives (2, 10, and 12 years), and just recently I got gobsmacked by a 43 year old doctor, mother of 2 who came into my place of work last month out of her scrubs.

Feminine gentleness and sensuality never age if a woman has them. So long as you're pleasant to be around, some normal body imperfections won't matter much to boyfriend. And if they do, then dump him.

KpopMusicFan · Answer

I am 45 my boyfriend is 28 . I don’t have body insecurities at all. I don’t have kids I am child free by choice. If you’re insecure about your body then maybe don’t be in a relationship. You need to love yourself and body before you can have someone else love you and your body.

SeriouslyNotSerious · Answer

If he reacts badly, then he's not the right guy for you. And you wouldn't want to be with someone who judge your small flaws, right? ♥️ I bet he will still love every part of you.

I have an auntie in her late 50s, and her current boyfriend loves her. And also her ex husband is still chasing her. 😂 Aaaaand.. she already have 5 kids! 😮

DeeDeeDeVour · Answer

You're putting too much into this.

In the first place, that young man already finds you attractive.

What he (currently) sees is what he gets and he already likes everything he's lookin' at.

Don't dwell on your past either.

It's unimportant.

Focus on looking forward to all the fun & bliss you'll share together.

Remind yourself that you deserve happiness.

strateguy632 · Answer

Those feelings are natural especially if you haven't done that in a while.

Still he saw your face n body shape while dressed so tell yourself he already knows n accepted you.

Also use a dim night light instead of the regular light, use excuse of romantic candle atmosphere/ environment.

Anonymous · Answer

He hasn't left you yet. You either chose a decent guy or you didn't. Only you can know that. Only you can know whether his words are genuine. The question is, are they? Or have you been deluding yourself. Do you get the feeling, impression any any way he's looking at other women. If the answer is "no" then you need to stop worrying about it. Did it ever occur to you that maybe you're giving him what other younger women are not? Genuine affection. Younger doesn't translate to more attractive when the heartfelt feelings are not there.

bobby_bush_eater · Answer

Well it seems all you can do is own it. You are who you are.

If he rejects you for literally who you are during intimacy and your age then suddenly becomes a problem so great he no longer wants you do you think that it would've lasted anyways then?

Anonymous · Answer

You said '' I'm an established middle aged woman.''

And with this in mind, you should know better. After all of the pleasure, physical intimacy, flirting, fun and novelty has calmed down, what are you left with? I think your 'insecurity' is the tip of the iceberg, it's more likely your spirit telling you to look for something that has real promise. Unless my assumptions are wrong in thinking you are looking for something more than just sex..

Anonymous · Answer

He's waayyyyy more insecure about giving you an orgasm. Remember that! He would probably leave you over his insecurity about measuring up and feeling like a man than because another girls young and her body is tighter.

Honestly, women's 30+ confidence has such an allure. Speaking as someone in their 20s.

PeachyPie93 · Answer

You can't really. You just have to believe in him and that he wants you. If he seen you in a bikini he knows what you look like already and he wants you, so get out of your own head and let him show you how he feels.

Nahid1707 · Answer

While you shouldn’t always take relationship advice from online  If your relationship is good  Why worry about this you know? You both are happy together  He is proud of you

Daniela1982 · Answer

I think your guy has a MILF kink going. After he is satisfied he will either dump you or keep you. You have to judge yourself. Are you worried your body just won't cut it?

Anonymous · Answer

I would say don't worry about it because the relationship won't last long either way. I was in several relationships when I was his age with women your age and it's just a stage guys go through... kind of looking for a mommy replacement. It's not a healthy relationship and it won't last.

bowenw · Answer

He obviously finds your attractive and interesting. It may help if you simply tell him you are a little insecure about being seen naked. I suspect he will love your body. Everyone's body has little flaws.

FreyaRed · Answer

Maybe it's his fetish. Milf, gilf, dilf whatever those guys names find for this fetish. It isn't uncommon.

nawtee_me · Answer

I would be willing to bet that you are absolutely gorgeous in your mom bod after what having kids has put it through. And if he doesn’t think that too then he doesn’t deserve to have it either.

DrPepper12 · Answer

Dive in!! You're as hot 🔥🔥🔥 as you wanna be!!! Stretch marks? You had two kids, he's not a moron. He's stacked? Why wait? Jump his bones!!

LiamJHayden · Answer

If he's into you, he will not care about a few wrinkles, stretch marks, or sagging. If he isn't into you, then he does not deserve your presence.

Rohaan2020 · Answer

Well that totally depends on his taste… personally i love being in bed with older women and honestly those stretch marks doesn’t matter much…. Older women are better in bed than the young ones who might have a great body…. So don’t stress too much

Friendlybro79 · Answer

Therapy maybe? Sounds like you got a lot to unpack. Also, you could tell him how you feel. My thoughts are he must like you to be with you.

TheLimeNan · Answer

If he's with you despite the age difference I don't he'll be put off by anything. If you bith want to move to the next stage and be intimate I wouldn't worry.

dudegreat91 · Answer

Its cool he is dating you cause he wants you naked. So you can show him what he wants. I love spending naked time with older cougars

art84 · Answer

If I was dating a women like yourself, I wouldn't matter what your body looked liked naked.

jahaims · Answer

He doesn't care. He knows he is getting the leftovers.

MasterKS · Answer

I think you thinking too much! Just be natural, insecurities are most mind game keep away from it!

Iron_Man · Answer

Go to the gym eat better

Anonymous · Answer

Stop dating babies.

Dating a Younger Guy: How Can I Overcome Body Insecurity and Fear of Intimacy?

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