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Original poster

To be shocked that my good friend, 37, is seeing a 66 year old lady?

359 replies

darksideofthetoon · 28/06/2026 19:59

Had a few beers with a good friend recently and got a bit tipsy and we got into his dating life. He told me that he’s been seeing a 66 year old grandmother. He is only 37 for reference. They met via online dating.

To be clear, there is nothing wrong with this but I’m just a bit shocked to be honest. He says that they enjoy each other’s company and there is no intention of it developing into anything more.

My friend has always dated younger women and not short of female attention at all.

It’s all good right?

OP posts:
Frugalgal · 29/06/2026 20:51

darksideofthetoon · 28/06/2026 19:59

Had a few beers with a good friend recently and got a bit tipsy and we got into his dating life. He told me that he’s been seeing a 66 year old grandmother. He is only 37 for reference. They met via online dating.

To be clear, there is nothing wrong with this but I’m just a bit shocked to be honest. He says that they enjoy each other’s company and there is no intention of it developing into anything more.

My friend has always dated younger women and not short of female attention at all.

It’s all good right?

Of course it's all good. He's a nearly middle aged, he knows what he's doing and so does she. All consenting.

Beeloux · 29/06/2026 20:38

shuggles · 29/06/2026 20:15

Sounds very old fashioned, extremely conservative, and anti-woman.

There is nothing unmasculine about a woman helping a man. Thinking otherwise sounds like manosphere Andrew Tate nonsense to me.

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As I said, you do you.

I divorced my xh for such nonsense when I was as 24 and he was older than me.

No regrets.

SkippitySkoppity · 29/06/2026 20:36

Of course it's fine.

I knew, with it being MN, there'd be some people stating there was a power imbalance. That's such a go-to phrase on any kind of age gap chat. But he's 37. He's a fully formed, almost middle aged adult (some would say already middle aged). Some people are unable to look at any kind of relationship as a fun temporary thing, as though people should always be striving for long-term. It's always 'but what about when she's 85 and he's 55'. Well it's highly unlikely they'll still be together, isn't it? But it's okay to have short lived sexual relationships. They can be fun and fulfilling and enriching.

FlyingBeGoat · 29/06/2026 20:33

darksideofthetoon · 28/06/2026 20:10

Without going into details, they’ve got to know each other very well in bed. My friend doesn’t do platonic stuff. He lit up like a Christmas tree when I asked him how it was in bed.

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I bet he did, she might find men her age can’t keep up and he might find women his age are planning for families- I imagine they are having as much unprotected sex as possible with no worries about unplanned pregnancies

Applesonthelawn · 29/06/2026 20:25

I think it's questionable if there's any kind of power imbalance and that can sometimes be subtle. Madonna's relationships for example might venture into power imbalance because of who she is. She embarrasses me generally though.
But if they're both just enjoying themselves, they should crack on.

Nanda66 · 29/06/2026 20:22

Who cares? They are both consenting adults and life is short.

AJLOAL · 29/06/2026 20:18

I'm 57 and seeing a 38 year old man. No one's business but ours.

shuggles · 29/06/2026 20:15

Beeloux · 29/06/2026 19:41

You do you.

Personally I grew up in a culture where the husband provides. I find men who leech off woman unmasculine.

That’s just my personal opinion though.

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Sounds very old fashioned, extremely conservative, and anti-woman.

There is nothing unmasculine about a woman helping a man. Thinking otherwise sounds like manosphere Andrew Tate nonsense to me.

PenelopeJoanSterling · 29/06/2026 20:02

Rpop · 29/06/2026 19:51

I know it doesn’t matter (and I genuinely think it doesn’t as long as they are happy) but I do think it is quite unusual. The main problem is when you don’t have a bedrock of experiences in common and were brought up in very different eras. similarly, one of you might need care while the other one is still quite young.

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even if you were brought up in different eras, you can still connect via hobbies etc, even same age gap relationships does not auto mean compatibility etc

BlueFahrenheit · 29/06/2026 20:00

Ilovegrantnicholas · 29/06/2026 19:47

I'm 65. You'd be surprised what we old ladies get up to!

You look lovely!

I know what you ladies are doing 😂

PintofFizz · 29/06/2026 19:55

darksideofthetoon · 29/06/2026 12:16

You must be reading a different forum to me or perhaps jaded by the men in your life.

This is not a man vs. woman thread - plenty of those on here already.

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Purely jaded by the men on MN

TamarindCottage · 29/06/2026 19:54

Coldwetlettuce · 28/06/2026 20:16

Why is there no intention of it developing into anything more if they go on hiking trips and trips away? Good on the woman for bagging a younger guy! And it’s refreshing to see that not all late 30s men want to date women in their early 20s, so good on him too

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@Coldwetlettuce is “bagging” a typo? 🤣

Tedsnan1 · 29/06/2026 19:52

riversofjoy · 29/06/2026 18:50

You dont think a 48 year old dating an 18 year old is gross?

🤮

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Who's 18?
My friend was in her mid 30s, as is the chap in the OP.

Rpop · 29/06/2026 19:51

darksideofthetoon · 28/06/2026 20:06

I have never seen this and seen a lot of things. Yes, I know some guys go for older women but the age gap is very large.

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I know it doesn’t matter (and I genuinely think it doesn’t as long as they are happy) but I do think it is quite unusual. The main problem is when you don’t have a bedrock of experiences in common and were brought up in very different eras. similarly, one of you might need care while the other one is still quite young.

OriginalUsername2 · 29/06/2026 19:51

Jane143 · 29/06/2026 19:07

What if it’s Harry Styles?? I would!

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I’d have to have given birth at 10 years old to be his mum 😆

Ilovegrantnicholas · 29/06/2026 19:47

I'm 65. You'd be surprised what we old ladies get up to!

To be shocked that my good friend, 37, is seeing a 66 year old lady?
BlueFahrenheit · 29/06/2026 19:44

Lararoft · 29/06/2026 19:38

Hmm well I’m 49, maybe I could date the 32 yr old physio at work that l like then!

I mean, if a 29 year old is ok for Sienna Miller at 44?

Date him. Have him twist you like a pretzel, too. Oh. I would! 😂

Beeloux · 29/06/2026 19:41

shuggles · 29/06/2026 19:25

@Beeloux Imagine when he’s 50 and she’s pushing 80. Most woman I know who have went for older men is because they’re rich. To me, it’s very unattractive for a man to be chasing a woman for money.

I don't understand why that's an issue. I'm finding more and more that the women around me make far more than I do, so I would certainly appreciate it if I was in a relationship with a rich woman and she was able to look after me with her finances. Why would I not want that?

You do you.

Personally I grew up in a culture where the husband provides. I find men who leech off woman unmasculine.

That’s just my personal opinion though.

southerngirl10 · 29/06/2026 19:39

Nope, just checked the UK totalitarian state rule book. No law against it - yet.

Lararoft · 29/06/2026 19:38

Hmm well I’m 49, maybe I could date the 32 yr old physio at work that l like then!

I mean, if a 29 year old is ok for Sienna Miller at 44?

UltimateSloth · 29/06/2026 19:38

I don't think people would be up in arms if the genders were reversed like some people are saying. 37 is a proper adult. People in their 30s of either sex can sleep with whoever they want without there being a power imbalance against the 30 something. It's not the same as when the younger party is a teen or just out of education.

8misskitty8 · 29/06/2026 19:36

He's nearly 40 so been an adult a long time. As long as he's not doing it to get her money/property then what's the issue ? Lucky her still getting a good seeing to in her 60's.
For all you know, your pal is a gigalo in his spare time. 🤣

BlueFahrenheit · 29/06/2026 19:30

If I'm single at the age of 66 and a 37-year-old man is attracted to me, I certainly will have a great time with him.

riversofjoy · 29/06/2026 19:30

AlgaeDreams · 29/06/2026 19:27

But there is a huge maturity and life experience difference between 18 and early 30s.
It's not really comparable other than mathematically.

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But people havent defined that, they have merely said 30 years?- no problem.

I disagree. I think there is something very wrong if you have to date someone 30 years younger than you. It shows a power balance that indicates something very wrong

Manifoldoptions · 29/06/2026 19:30

RosieSpring · 29/06/2026 19:06

OP said he's well off and the woman is comfortable too.

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She may appear so and so might he….but appearances can be very deceptive. It doesn’t matter how he appears but if she appears to be wealthy I’d be more cynical. You can try to guess but it’s really not possible to guage other people’s wealth. No way a young man would be up for it with a woman that age in my opinion unless he thinks he’s up for a cut. Sorry - very very cynical…..

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