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Should I go on a date despite a 20 year age gap?

205 replies

UndecidedOtter · 23/09/2026 15:49

I (M50) do an activity with a bunch of other people once a week. I've made a few friends and there is one woman who walks in the same direction as me towards our respective homes. I've really enjoyed our chats over many weeks.

Yesterday, we stopped for coffee on the way home, not for the first time and she asked me out on what is definitely a date. I was very surprised she would find me attractive. I would be happy to continue with her as friend, but she is gorgeous, and now realise I have been suppressing the fact that there is chemistry between us. She is single with no kids, as am I.

Now we come to the issue. She is in her early 30s so there is a 20 year age gap. I am reluctant to go on a date with her, not because we don't have enough in common, but because of that difference. I'm already thinking of a future where she is 50 and I am 70. I know that sounds a bit ridiculous and I'd love to go on the date otherwise and just play it by ear, but I have these doubts.

What do you think?

OP posts:
ForeverTheOptomist · 25/09/2026 20:20

So there's a 20yr age gap, so you're in your teens, right?

Sorry. Being silly. I can't see anything wrong with have a relationship with someone younger. I think the thing that you do have to accept if you do get serious is that you would probably pass before her and when she's still relatively young.

Chickadee001 · 26/09/2026 15:07

Go for it, life's too short for what ifs! I generally had older boyfriends when I was single, I found them far more interesting and polite!

How weird that I'm now happily married a guy 10 yrs younger though!!😍

UndecidedOtter · 28/09/2026 12:32

As promised, I am reporting back.

We went to the aforementioned National Trust property and geeked out over history. I brought a picnic, centred around cheese because I read that cheese can "fascinate a woman." We had a lovely time, held hands a bit, and ended up having cocktails.

She did not want to talk about serious stuff on this date, just have fun. She very much implied she wants a physical relationship, I warned her that I am not great at that, and she said those words every man wants to hear "don't worry, I am very easily pleased in bed!"

I have asked her out for dinner later this week.

While I am giddy, I am still very unsure about the whole thing and I will make sure I have a proper conversation next time.

Thank you to all posters for your help and advice.

OP posts:
JohnofWessex · 28/09/2026 12:45

😀

AllezAllezPronto · 28/09/2026 13:03

UndecidedOtter · 28/09/2026 12:32

As promised, I am reporting back.

We went to the aforementioned National Trust property and geeked out over history. I brought a picnic, centred around cheese because I read that cheese can "fascinate a woman." We had a lovely time, held hands a bit, and ended up having cocktails.

She did not want to talk about serious stuff on this date, just have fun. She very much implied she wants a physical relationship, I warned her that I am not great at that, and she said those words every man wants to hear "don't worry, I am very easily pleased in bed!"

I have asked her out for dinner later this week.

While I am giddy, I am still very unsure about the whole thing and I will make sure I have a proper conversation next time.

Thank you to all posters for your help and advice.

How lovely.

Look- don't spoil this by getting too serious too soon.
Have a few more lovely dates and all may become clear.

If she says she wants a family, that is something you need to think about.
(I do know a few men who had 2nd families in their early 50s, but of course that may not be your cup of tea.)

I think the children issue is the most important. But don't bring it up- see what she says.

SaraHoliday · 28/09/2026 13:07

UndecidedOtter · 28/09/2026 12:32

As promised, I am reporting back.

We went to the aforementioned National Trust property and geeked out over history. I brought a picnic, centred around cheese because I read that cheese can "fascinate a woman." We had a lovely time, held hands a bit, and ended up having cocktails.

She did not want to talk about serious stuff on this date, just have fun. She very much implied she wants a physical relationship, I warned her that I am not great at that, and she said those words every man wants to hear "don't worry, I am very easily pleased in bed!"

I have asked her out for dinner later this week.

While I am giddy, I am still very unsure about the whole thing and I will make sure I have a proper conversation next time.

Thank you to all posters for your help and advice.

Great news! ♥️

Lmnop22 · 28/09/2026 13:40

Do you mean she wants JUST a physical relationship or she just wants sex to be a part of her relationships (don’t we all?!)

UndecidedOtter · 28/09/2026 13:50

Lmnop22 · 28/09/2026 13:40

Do you mean she wants JUST a physical relationship or she just wants sex to be a part of her relationships (don’t we all?!)

I think the latter. We already have a good friendship, and the idea of her picking me for a physical relationship makes no sense at all.

OP posts:
DangerousLesions · 28/09/2026 13:58

Flippin heck. You sound like something from a Merchant Ivory film. Are women really fascinated by cheese? Intriguing. Very happy for you that the date went well.

UndecidedOtter · 28/09/2026 14:12

DangerousLesions · 28/09/2026 13:58

Flippin heck. You sound like something from a Merchant Ivory film. Are women really fascinated by cheese? Intriguing. Very happy for you that the date went well.

It's a bit of a meme. I thought it would be funny (plus I know she likes cheese)

www.snopes.com/news/2021/01/22/the-spellbinding-history-of-cheese-and-witchcraft/

OP posts:
CallmePaul · 28/09/2026 14:31

DangerousLesions · 28/09/2026 13:58

Flippin heck. You sound like something from a Merchant Ivory film. Are women really fascinated by cheese? Intriguing. Very happy for you that the date went well.

I don't know either, but this is a 50yr old man who is getting attractive 30 yr olds asking him out & want to sleep with him. I'm his age. Well 3 yrs older, I do not get this.

He may be the new non toxic Tate, I do not know, but I'm stocking up on cheese just in case he is some sort of guru. 😆

DangerousLesions · 28/09/2026 14:49

CallmePaul · 28/09/2026 14:31

I don't know either, but this is a 50yr old man who is getting attractive 30 yr olds asking him out & want to sleep with him. I'm his age. Well 3 yrs older, I do not get this.

He may be the new non toxic Tate, I do not know, but I'm stocking up on cheese just in case he is some sort of guru. 😆

Yes, he could be! Is there something in the cheese, I wonder.

CallmePaul · 28/09/2026 15:06

DangerousLesions · 28/09/2026 14:49

Yes, he could be! Is there something in the cheese, I wonder.

There is only one type of cheese I can think of that would possibly have the power to make attractive 30 yr olds fancy me, it's that famous religious cheese from the middle east.................................
..
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.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.

Jesus of Nazereth

😁

CallmePaul · 28/09/2026 15:18

Also as a novice in this cheese luring game, I won't rush things. I'd tread Caerphilly 😄

That's me done for cheese gags today, before everyone gets feta up with them. 😉

DangerousLesions · 28/09/2026 15:22

CallmePaul · 28/09/2026 15:18

Also as a novice in this cheese luring game, I won't rush things. I'd tread Caerphilly 😄

That's me done for cheese gags today, before everyone gets feta up with them. 😉

Edited

Agree. One would brie silly not to.

AllezAllezPronto · 28/09/2026 15:47

CallmePaul · 28/09/2026 14:31

I don't know either, but this is a 50yr old man who is getting attractive 30 yr olds asking him out & want to sleep with him. I'm his age. Well 3 yrs older, I do not get this.

He may be the new non toxic Tate, I do not know, but I'm stocking up on cheese just in case he is some sort of guru. 😆

I have a close friend who at 51 married a woman of 35/36.
She was divorced though with children (and no ex on the scene to complicate matters.)

Now, 30 years on they are still together and happy.

Does another 5 years make a difference to your opinion?

EtsyKetsy · 28/09/2026 16:04

The happiest couple I have ever known had a 16 year age difference.

TheBayHorse · 28/09/2026 16:15

Glad to hear it went well. Ignore the pearl clutchers and crack on.

Friends of mine (married 20 years) have a similar age gap and met in their early 30s/early 50s. The were friends first, similar financial situations and have shared values and interests. They seem very happy and have chosen not have children.

UndecidedOtter · 28/09/2026 16:30

@CallmePaul I despise Tate and his ilk, and literally the only negative thing about her is her age.

OP posts:
Chatterlyssecret · 28/09/2026 18:35

An opportunity like this won’t come again, go for it & no holding back.

CallmePaul · 28/09/2026 22:28

AllezAllezPronto · 28/09/2026 15:47

I have a close friend who at 51 married a woman of 35/36.
She was divorced though with children (and no ex on the scene to complicate matters.)

Now, 30 years on they are still together and happy.

Does another 5 years make a difference to your opinion?

I have no problem with it. I may have given the wrong impression there with a badly worded post. I meant I do not get it, as in I'm almost OPs age, also male. I don't get attractive 30 yr okds asking me out.

I think he's a lucky rascal & should enjoy the moment.

I know a larger age gap that's worked well so far, I think it was 24f & 46 or 47m. And strangely not a sugar daddy type situation at all. Married 2 kids now. Seems to be going well.

CallmePaul · 28/09/2026 22:32

UndecidedOtter · 28/09/2026 16:30

@CallmePaul I despise Tate and his ilk, and literally the only negative thing about her is her age.

Yeh I hate them too, toxic scumbags infecting boys & young men with their horrible views. In jail now, hopefully for a long time & their empire comes crumbling down & exposed for the utter abhorrent crap that it is.

mrsturkey · 28/09/2026 22:38

Glad you went!

Have fun and be happy

ClairDeLaLune · 29/09/2026 10:14

UndecidedOtter · 28/09/2026 12:32

As promised, I am reporting back.

We went to the aforementioned National Trust property and geeked out over history. I brought a picnic, centred around cheese because I read that cheese can "fascinate a woman." We had a lovely time, held hands a bit, and ended up having cocktails.

She did not want to talk about serious stuff on this date, just have fun. She very much implied she wants a physical relationship, I warned her that I am not great at that, and she said those words every man wants to hear "don't worry, I am very easily pleased in bed!"

I have asked her out for dinner later this week.

While I am giddy, I am still very unsure about the whole thing and I will make sure I have a proper conversation next time.

Thank you to all posters for your help and advice.

Aww that’s lovely OP, I’m glad you went and had such a good time! Good for you. Don’t forget to update us about the second date!

JohnofWessex · 29/09/2026 13:00

I have just sent my suit to be cleaned and am polishing my shoes for the big day

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