If you haven’t done it by 50 you never will.

If he wants his own children (and doesn't want to be a step dad) then by definition he will have to meet a woman, 20 or so years younger than him.

Unless he is successful, handsome, charming and waa-ay above average it is unlikely that this will happen.

Oh that's just stringing them along. Is he actually um intimate with them?

@ElleintheWoods I can totally relate to this and was the exact same until I met someone.

It baffles me that so many people are uncomfortable with people making their own choices and not settling until they find what works for them.

A good relationship is far better thsn one just for the sake of it.

It feels unlikely at this point. He’s been a commitment phobe for decades and has little insight into his situation. Does he live with your parents still? Not much is talked about male fertility but it does deteriorate over time. Would a woman in her early or mid 30’s be interested in a man in his 50’s who has had no serious relationship and describes his girl friends as “friends”? The reason why l say woman of this age is their most likely better fertility will help offset his most likely impaired fertility. That’s before you even get to the compromise that long term relationships and parenthood require etc

This an interesting hypothesis. My DB is 48 and currently single (never married and no children). Plenty of relationships that all seem to fizzle out around 2-3 years or less. I think he is nit-picky and has a controlling personality which doesn’t help. He enjoys the honeymoon phase and then his boredom kicks in and he looks for faults in the relationships. Some of his exes have been absolutely lovely. Nice families. Parents all get on well etc.

He has now found himself an overseas girlfriend who he’s been visiting and conversing with for a couple of years now. They finally sorted out her visa (3 yr visa) and she is now living with him. They have discussed marriage in the future and he has agreed to one child (how mature of him😂). She is about 33yo.

Am I being unreasonable to tell him to quit wasting her time if he’s still messing her around in about 18 months time/not committing to a marriage? It annoys the hell out of me when I see women who waste their child-bearing years on a guy who future fakes or is just “not sure she’s the one”. I’m a firm believer that you know pretty quickly if you can see yourself marrying someone and having children with them, especially if you’re living together.

My ( male ) friend from late teens/ early 30s is 57. He has never been married. He had a few girlfriends over the years. Even after they split up no one had a bad word to say about him.

FIve years ago he started going out with a woman in her mid 20s. They didn't pursue each other but met each other from a pub circle of friends. The friendship was a slow burner that turned romantic. They now have a seven month old son and are getting married in August.
Even after 5 years, when the honeymoon period is over they are both smitten with each other.

Don't have the experience of settling down later in life as such (however, one that does sprig to mind is George Clooney 😂), however I can see where your brother is coming from.

I'm late 30s and frankly I haven't been with anyone where being with that person doesn't feel like 'settling for less'. It's not that I am looking for something crazy, it's more that I am hypercritical of people and if they make my life more draining rathern than easier and better, I keep them at arm's length. I don't really fall in love.

I did fall in love in my very early 20s and he seemed like the perfect match, for many many years I thought he was 'the one' while being with other people, and almost chasing that feeling of what being with him felt like.

It's also not that I date 'below par' men. A few examples of relationships or potential relationships I've pulled out of:

• MP - super interesting person but thought he had mental health and substance abuse issues
• CEO of a household name company - likewise, substance abuse and extreme levels of stress/unhappiness
• Premier League footballer - extremely attention-seeking, lifestyle revolved around parties, women, alcohol
• Model - very good-looking but also very insecure, lacking direction in life
• Tech guy - unconcerned with external presentation or social grace, extremely matter-of-fact, antisocial
• 'Normal' guy - again, antisocial, thinking of anything like a day out or trip to another city as a big deal
• Guy from work - life revolved around drinking and football, social life heavily revolved around seeing his family
• Another guy from work - focused on his own career progression and having an easy life, often complaining, no real thought about wider social issues or problems of the world

As you can see, I am able to find something wrong with absolutely everyone, whereas I am sure many women would find these men quite dateable, especially the higher income ones.

Or perhaps I attract difficult personalities and they are single for a reason, who knows.

What would I like? I'd like someone established in what they are doing, perhaps an artist, scientist or writer, or another profession that revolves more around their purpose and less around making money, that has a calm, thoughtful nature and curiosity about the world, broad range of topics etc...

Would I find that? Maybe, but not easy. My first thoughts upon meeting somebody is usually outlining what is wrong with them - unless it's attraction at first sight, which is extremely rare.

I don't mind if I stay single-ish for life with a string of short relationships, a bit like your brother, as long as I am true to myself and happier outside a relationship than in one. Being in a relationship is not a goal in itself for me.

At this stage of life I feel like I can relate strongly to the 'eternal bachelor' lifestyle. I do need connection and intimacy, but I am unwilling to commit to something/ someone that negatively disrupts a lifestyle that works well for me and isn't aligned with my identity and choices.

Apologies if that's not what you were looking for on here, but perhaps this helps you understand your brother's mind better.

I had a relative in an almost identical situation. She had a demanding career in a male-dominated field and didn’t marry (or have any partners who I knew about) until her 50s when she met a widower and later married him. They were together until he died, by which time she was also in her final years.

I don't know. After 2 long term relationships, I spend a lot my 30s single.

I dated lots and enjoyed it but nothing ever seem fully right. I had loads of people telling me I was too fussy and that I was looking for something that didn't exist or seeking perfection.

In my late 30s, I met someone that was right, everything was easy and we just clicked. Bf had been single a lot longer than me and also had people telling him he needed to settle down etc.

How about giving him some credit for knowing his own mine and not settling due to societial pressure.

He's not stupid. It's not like he doesn't meet women or stuggles with dating. He knows what he wants and prefers to keep looking rather than settling just for the sake of it.

It's his life and his choice.

I agree that he may meet an older divorcee / widow with her own DC who has zero interest in merging her money, household etc and it suits her to have a boyfriend for dates, holidays, events. Both would then bring the same upfront, low commitment energy to the relationship and are clear on boundaries / expectations etc.

I think he has some work to do around understanding unlived lives - how when we make one choice and open one door, other doors for what could have been have to close.

It's important that he understand the good reasons he chose this path so that he doesn't get bogged down in regret. Some good parts are he has never had to share his finances which gave him economic freedom, his choice not to commit means he has spent time with lots of amazing people and have fun life experience, but I'm sure he can think of others.

The main thing is he has a core belief that there is a 'one' out there for him, and he cannot settle for less that the one. This is a romantic idea, and many of us decided that we were willing to compromise and accept everyone is flawed, and work together on compromise. Your DB needs to ask himself if he could ever get to that mindset. Could he list out non-negotiables and negotiables, and approch it like a job application where he dayes people who meet the 'essential' criteria and can learn to navigate the absence of desirable ones?

Maybe not, in which case he can say 'in my quest to meet 'the one' I accept I may never find her, but I still think it was worth trying'

Reverse that.

Anyone else is going to find him very difficult to live with because he'll be so set in his ways.

That said I do know a lovely couple who met post 50. They decided to actively not move in together and instead retain their own spaces whilst cohabiting part time.

Does he mean he wants a family or is he saying this to appease his Mum?
I am generally of the opinion that if you REALLY want to do something in your life then, in general, you will find a way to make it happen.

In that he's had lots of girlfriends but just doesn't fall in love. Plenty of time for it, but it sounds as if he blocks it emotionally.

No judgement about it. I've got a block on emotional involvement. But it's better to be honest with yourself about it. Never falling in love with anyone and still believing you want a partner and a family is delusional.

That's incredibly selfish. And I know someone in his 60s with toddler children. He's on his knees with it and in all likelihood will be gone before they're 20.

Very sad.

Sorry but in what way has he “missed the boat” for a partner?

I think it's more common than people think for men to be slower to "settle down."

A work colleague of mine got married a couple of weeks ago. She's mid-50s and has been divorced for at least 10 years, with 2 young adult children. He's late 50s, never married, until now.

He's in his 50s. He's too old for a family. Possibly a partner, although it sounds to me as if he's missed the boat for that too.

Some people just aren't the settling down type. There are plenty of divorced people who have found that out the hard way.

Your brother seems happy with his life as it is now. Maybe he’ll meet someone or maybe he won’t, but if he does meet someone he likes, isn’t it up to both of them to try and make a go of it. I don’t get why you’re coming online to talk about him in these terms - he’s not hurting you, is he? Also, your mum will be fine. Whatever will be will be.

I think there are genuinely a few people out there who just don't meet their person until later in life because they're a little bit different, or that's just how things unfold for them, but I don't think your brother is one of them. Met loads of versions of him!

If there was nothing more complicated going on below the surface then why does he always end up dating women who want more, and who break off with him? It's a pattern.

As he gets older it will be interesting, as I think many older women are happy to have low commitment relationships (don't want to cohabitate or share finances and having kids is off the table). I wonder if he'll start dating these types of women, or continue with women who he can get an emotional kick out of rejecting (even if it is on a subconscious level).

Or will he take a leap with a younger woman, as he feels his youth slipping further away? Who knows!

I have 2 old schoolfriends, lovely chaps, well-educated (doctor & structural engineer) who have never married. I also have an old schoolfriend (trading standards officer), who is female and never married.
I assume they just never met anyone that set off the spark.
They have all had relationships at some point, but all single now.
Sometimes it just doesn't happen.
By the same token I knew an absolutely adorable couple, both classical musicians, who didn't meet and marry until in their 50s, so sadly too late for children.

To be fair op says he usually dates close to his age. But if he wants kids the woman would need to be quite a bit younger than him, I don't think it's lack of emotional maturity to know that! (Unless he'd be happy with step kids, but that can be messy).

I do think he's less likely to find a long term relationship of a family is a criteria at his age though, as not many women wanting kids would be keen to do so with someone in their 50s. I went to a wedding of a 50 yo man who'd never been married before recently, so it certainly happens, but they won't be having a family together, the bride is already a grandmother. So he may need to adjust his expectations.

It does seem like you are making this a bigger problem than it is though, it feels a bit like Bridget Jones when the smug marrieds are pontificating about why there are so many singles. He's obviously fairly happy or he wouldn't have turned down so many chances.

I think he will probably end up surprising you. People love to pigeonhole others, especially when it makes them feel superior to do so.

It's unlikely he'll get what he wants because he's being a complete headfuck for the women he tolerates whilst waiting for a better offer to come along. And because he's going on about a 'family' without genuinely accepting that the #1 prerequisite for that is a woman that isn't a 'friend', but a partner.

After all, at his age, he's now looking for a significantly younger woman who will find him attractive, enjoy his company, want to be with him, be prepared to tolerate his shit and then, if by some miracle she is prepared to endure the fannying around in the hope that <random celebrity-influencer-Only Fans type> falls at his feet for long enough that he decides he's actually going to honour her with some real human emotion and mutual support, risk getting married and having a kid with him.

There's vaguely, slightly, maybe a chance in a million that he'll get hit by a thunderbolt. But there's even less chance that a woman he feels like that about is going to feel the same about him.

He can be saying anything he likes to the two of you.

I have a SIL who is like this, I’m bored of the whining about it and it dominating every family get together after 3 decades.

Just let him get on with it.