sass c. in love

Older Men – What I’ve Learned While Dating One

“I have gone out with younger men, and they’re great fun; they’ve got enthusiasm. Stamina! But I think older men are much better lovers.” – Jerry Hall

If you’ve been following this blog for a while, you may have noticed that my lover and I are in two different stages of life. He has a kid and I feel like I was kid just yesterday. Lover is older than me and we’re not talking 4-5 years older; it’s more like 10+ years older. What we have going between us is good, but dating older men does not come without its challenges. Here are some things to consider when dating with a big age gap.


It’s more acceptable for older men to date younger women than it is for older women to date younger men. But, judgments are still cast on the younger women dating older men.

When we’re in our 20s or 30s dating a man who is 10+ years older can get us branded as a sugar baby. People think that we’re only dating an older guy because he has more money and we’re gold diggers. Many people will think that we have sex with older men so that will take care of us financially.

I think when you’re older, it’s not so much of an issue. This is possibly because women in their 40s+ seem to have more stable careers and have established themselves. If a 48 year old woman started dating a 63 year old man, it would be seen a non issue.

I often think about how I would introduce him to my family. Right now, we’re pretty much a secret from our families. His kid and ex know that he’s seeing someone, but they don’t know how serious it is or who I am. For me, only a handful of friends know, but the details are also left out. How do you introduce someone with such a big age gap to your family and friends? Surely, you will be met with a lot of judgments and unkind words.


Perhaps this bit will bum you out somewhat, but when you’re in your 20s or 30s and you’re dating an older man, you may find that he has kids of his own. His children will always be his number one priority over you. You can either be on board with this or just stay away from dating single fathers.

I’m on board with lover’s kid being his first priority, but it doesn’t mean that it’s always easy. I haven’t meant his kid yet and I’m not sure if that will come anytime soon. But, we do talk about his child and different things the child is going through. He not only needs to be there for my emotional needs, but his kid’s emotional needs as well. This means he has more responsibilities and at times, that means he has less time for me.

But, I’ve found myself caring about his child as well. In no way am I helping him parent his child, but I love him and his child is a part of his life so by default I’ve come to care about the kid as well.


It may not be with every older man, but I think some older men who have been married and divorced have trouble with love. It’s not necessarily their capacity to love, but it’s almost as if they have a hard time being open to love again. Their ex was terrible and it left them a bit scarred and yes, this can happen to female divorcees as well.

With lover, it can at times be challenging because of how jaded he his. How did I fall in love with a man who has a hard time with being loved? I have no clue, but what we do have is special and I really do love him.

It takes a lot of patience and at times, I don’t have any, but he is worth the wait. Empathy also plays a big role as you have to understand that they are still in pain. We may be able soothe some of that pain, but it takes time and work to heal. When lover is distraught, I have to just wait and listen. I let him that I care about him, but sometimes, he isn’t ready to talk about it and that’s when patience is a huge factor. Sometimes, it’s a few hours and other times, it’s a couple of days before he feels ready to talk. I hate the silence, but I have to understand that he needs to deal with some things.


The future is unknown. I really don’t know what will happen between lover and I in the coming months or even years. I’ve always dreamed of starting a family, but reality is that “family” may look a little different when dating older men.

We might not ever have kids together and he might not want to get married. But maybe the definition of family isn’t so binary. Could he also be my family if we’re long term partners? Or maybe lover, his kid, and I would become some form of a family unit.

It’s definitely something to consider as if you are dead set on having kids of your own, it might be harder if there’s a big age gap. I also have to think about if I have a kid five years from now, he’ll likely never see them get married or meet his grandkids. But I love him so he is enough for me.


Let me tell you, older men win the gold medal for being better lovers. While there are some who never grow up and continue to act like players as if they’re still 26 and living in a bachelor’s pad, there are many others who have grown out of that phase. There’s no games, no bs.

It’s not just in terms of sex, but I’ve noticed that when I’ve dated older guys, they do a better job at caring for me. They make sure I feel loved and cared for.

But, let’s talk about the sex. So lover and I don’t have super crazy sex lives. Yes, we have a lot of sex, good sex. It’s not super kinky, but he’s definitely not selfish. For some reason, all the guys I’ve dated that were closer to my age seemed to have an aversion to going down on women. That has not been the case with the older men I’ve dated. Lover uses his tongue to give my cunt all the attention before he pounds into me and I love when he goes down on me.

He also cuddles me with and wraps his body around mine after sex or what we’re watching TV. There’s a lot of affection. We hold hands in public and kiss in the middle of the street. He makes me feel loved indeed.


Lover is not a big texter so sometimes, I get a bit frustrated. He sends me one word answers that make me feel like he’s not really interested in me. But where he lacks in texting, he makes up for when we video chat or talk in person.

It’s definitely important to keep in mind how you communicate when you date someone in a different stage of life. Maybe you’re in your 50s and you want to date someone in their 70s. While many in their 70s have become really hip with it and learned how to use a cell phone, some haven’t and you may have to resort to just phone calls and talking in person.

I’m big on texting as it makes my life easier, but this is only true with friends. With romantic partners, I’d rather talk on the phone, video chat, or talk in person. When I’m talking to a romantic partner, I want to hear their voice because it makes me miss them a little less. However, when it’s just a friend, I’d rather text so I can answer whenever I feel like it.

With lover, we can’t always see each other, talk on the phone or video chat because we’re trying to stay on the down low. His kid is often around and my family is often around. There’s very little privacy. While I’d love to see him and hear his voice more, it’s not always feasible which makes his texting style a challenge to deal with at times, but I still love him.

Yours Truly,
The Sassy Sub Daily

Image from Unsplash

sass c. in love - older men

sass c.

i'm just your average girl with a dirty mind. young, asian and submissive...does that pique your interest? constantly in a battle with myself whether to stay confined by my cultural values or to break free like the freak i am.

Instagram: @thesassysubdaily
Twitter: @sassysubdaily

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  1. I have once been with a man 20 years older than me, and he was a damn good lover, knew exactly what to do and when to do it, and read my body like a book. I hope your dreams with your lover come true, Sass, and that you will be together for a long time!
    ~ Marie

    1. Lover is nearly 20 years older than I am. Many guys my age like to brag that they have better stamina, but I’m not so sure about that because so far all of the older guys have lasted a lot longer hahaha.

  2. howie1320 says:

    This was a facinating insight to the warm caring person you are sass. As an older guy I can tell you that we are as old as the person we feel.

    1. I think sometimes, older men think the younger girl will leave them. I know that lover certainly thinks this way. He acts as if I’ll get bored of him eventually and want out. I try not to look at the relationship in terms of the age gap, but more so by the chemistry and effort put into it.

  3. howie1320 says:

    People are different ages in their minds. I have to keep reminding myself I’m not 30 anymore. I can fully relate to ‘lovers’ concern though. I’d feel the same if I were him🤔

    1. If a girl who used to jump from one guy to the next, stays for eight months and continues to say she’s not going anywhere, I think it should reassure him. I sort of think it’s his excuse not to commit. I feel older than I am (in terms of my mind), so it’s probably why I get along better with older men.

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