He does not work. What hard questions should I ask?

[lovelivesherenow]

I met a lovely man who does not work anymore.
He saved up and got out of the 9-5 life decades before one would.
I'm dating for marriage ultimately. Any ideas of the kind of questions to ask or things to look out for to help me work out whether he'd be right for the long haul?

"If that's OP's fiancé - well done"

How did you make the leap from a couple of coffee dates to "OPs fiancé"?

I wouldn't ask. I would just see where it goes. Two coffee dates is very early days.

He ain’t gonna want children at 50 and retired! I’d say you are incompatible from that point of view. And you don’t have the time to waste on it.

No, think he lives in my village apparently with his wife and kids and not even sure he’s 50 yet

A 10 year age gap may not seem much when you are 40 and 50, but the gap can widen as you get older if the eldest of the two partners develops health/mobility problems. You could find yourself a carer in your early 60s to a man in his 70s.

Or leeches maybe?

I know a couple of men like this: worked all the hours in IB, never spent their bonuses, bought modest houses for cash and drove Skodas while their colleagues were getting million pound mortgages, Porsches, trophy wives and locking themselves into expensive school fees for the next 3 decades.

They both retired early 30s and seem to spend most of their time snowboarding, cycling, and setting themselves big 'challenges'. They both volunteer (as kids sports coaches). They live pretty charmed lives and now in their late 40s I can't imagine either of them would want the burden and responsibilities of parenthood.

As an aside, I find the though that if you don't work you would just slob around the house all day bizarre. If I didn't have to work I would do so much more actually important stuff - I assume most people are the same? Most people work to live, not the other way round. Think of all the time you would have for hobbies, projects, music, sport, activities, exploring, travel, volunteering if you didn't have the bind of 8 hours a day working.

The only person I know at 50 who doesn't work (excluding SAHP and those with illness) is a multi millionaire who sold up his company at 42 and has spend the last 10 years travelling, playing a LOT of golf, bit of volunteer work and many lunches. He's great company and him and his wife lead a charmed life from what I can see.

I cannot see how someone in his position would want to start a family but if that is important to you then stop pissing about and be up-front if not on the next date then pretty soon after -

"can I ask how come you don't need to work?"

"can you see yourself married with children? I'd like that eventually and do think it's important to be up-front with someone I'm seeing beyond the first few dates in case it's not in their life plan"

And this. You’ve had 2 dates with a bloke and you’re wanting to know how much dosh he has?

you need to know if he wants kids, that’s your deal breaker, but somehow too you need to plan this bit of your life out yourself. Without a partner. You don’t have years to wait here, you know this.

Most people who are dating won’t want to have kids in the first few months of knowing someone, and those who would often are the LAST people you should have kids with.

if you give off the time’s ticking vibes, that desperation will potentially make you vulnerable to some really bad men.

I'd want to be confident that he had sufficient money to be able to afford to do the things I wanted with me without me needing to subsidise him. I'd want to be sure he had a full life and wouldn't be clingy and needy, expecting me to fill his long hours for him and getting under my feet.
I would also want to know he did something useful with his time such as volunteering. But that's just personal, as I'd find the idea of a priveleged man who did nothing to contribute to society, and focused only on his own leisure while spending money his grandparents earned incompatible with my values. But that may not be an issue for you.

Just run a mile if he tells you he has a sudden 'cash flow problem' and needs you to 'lend' him £10k until it's sorted out 😜

This sounds like my Dad. Worked very hard for the first 25 years of adulthood (to the detriment of his relationship with his wife and kids) and has the gift of the gab so got promoted regularly. He now has enough passive income from rental properties to live on for the rest of his life, even after divorcing my Mum Hasn't meaningfully worked for the last 15 years.

He's very active, so is out and about a lot. Spends 4 months of the year travelling Europe in his van. He's not conventionally rich, doesn't have huge amounts of cash to splash around, but has enough passive income coming in every month to pay for what he needs.

2 coffee dates...

I'd be remembering my golden rule about dating...

IT'S ALL BOLLOCKS UNLESS I SEE IT FOR MYSELF.

"I'm 39 and I work in the city...."
Yeah, he was 44 and did work on the city... As a cashier at a WHSmiths, which is a fine job so why lie?

"I'm single, 38, I love hiking and being outdoors."
He was 40 and on our first hiking date he got exhausted after 30minutes and admitted that his idea of 'hiking' was a gentle stroll from home to the pub.

And probably the most relevant:
"I made a lot of money in my younger days so now I'm over 40 I just work part time and use the rest of my time doing what I enjoy."
He was broke, £30k of credit card debt but still insisted on working part time with a top up from Tax Credits and the house he said was his?... Was his friend's place and he actually had a room in a bedsit.

It's no wonder I quit dating really. 🤣

Sorry Op but after 2 dates, getting to the bottom of where his money came from is frankly none of your business and asking ‘hard questions’ a this stage will make you look like a gold digger

And can only echo what others have said, it’s extremely unlikely an early retired 50 year old with plenty of free time is looking to be a new dad. If that was what he wanted from life, he’d have done it already.

And absolutely agree that you need to take action now if you want children.
Even if he is 'the one' (highly unlikely on date 2!) you are potentially years off starting a family if you take the conventional route of house/marriage etc. And yes plenty of women have children at 42/3+ but many can't plus it's riskier.

If you are adamant you want to birth your own child(ren) I'd be looking up a local sperm bank ASAP.

He has had a lifestyle with very little restriction on what he does for 5 years, he has prioritised that. He’s likely to not want to give that up which could be seen as ‘selfish’ in a romantic relationship. I think it’s unlikely he wants children and if he had them he wouldn’t want to curtail
his lifestyle. How important are children to you given you’re already 40?

I was in a position at 46 to retire (but didn't). However if I had retired and someone I had only just started seeing had questioned me about how I could afford it and how I was managing my finances it would have been a huge red flag for me. It would be my business and I would only discuss my finances with someone I felt seriously about. If he isn't volunteering the information then I really don't think the OP has a right to try and elicit this information.

I realise the OP wants to make sure this man is a good candidate as a life partner and father, but imo at 50 he is already out of the running surely? Just my opinion but in my experience men who want to be fathers have usually had children way before they reach 50. Also, consider the possibility he has used FIRE to set himself up, then he has been successful at that technique in part because he hasn't had the cost of having a child/children to consider. It may be that he has planned his future financial arrangements pretty much based on maintaining his own lifestyle alone, and won't be able to, or want to take on any dependent wife or child.

But, if the OP really wants to find out if he is a potential partner/husband/father, then it might be best for her to be open one and simply explain her position, ie that she is now at an age where time is not on her side, that she very much wants children, but that she also feels the need to make sure a potential partner and father for her child is truly willing and financially able to take on that role. That leaves the ball in his court. If he sees something that could be serious in the relationship then he then has the opportunity to explain his position, and if he doesn't then he's probably not interested in anything other than a low commitment but perfectly lovely casual relationship.

Do you really think that someone who's 50 and retired 5 years ago is going to want to start a family??
I know a couple who retired as they hit 50 - they had very well paying jobs, lived in a relatively cheap area, didn't have kids and don't live a flashy lifestyle. They're currently enjoying their hobbies and travelling around the UK in their campervan. I'm not at all jealous!

"can you see yourself married with children? I'd like that eventually and do think it's important to be up-front with someone I'm seeing beyond the first few dates in case it's not in their life plan"

This is the crucial question really. I think you should ask this first and then see what he says. At 40 you haven't got time to waste on someone who does not want children.
I very much doubt he would want children at 50 living the lifestyle he has now. Children would make a huge difference and he'd be facing 20 years of bringing them up with you and having to make sacrifices to his lifestyle. There's a remote chance he might want to do that and be prepared to give up activities etc. to bring up children but I'd be very very careful OP. You wouldn't want to marry him, have children and then he starts getting resentful because there's been an enormous change to the lifestyle he's become accustomed to over the last decade or so.
If he says he does want children, the next thing is to establish why he hasn't had them before he was 50. Yes, it sounds awful, poking your nose into his past and his business, but I think it is important to know. (I'm assuming from your post he doesn't have children already as you don't mention them, but perhaps he does). Men who want children normally have them long before they are 50.

You also need to know a bit about his relationship history. I'm very wary of cocklodgers having had bad experiences with 2 of them, so maybe I have become paranoid. Not all men are cocklodgers!! But, if he's got a history of moving from woman to woman, usually successful women with their own properties, then you need to be very careful. That's different to him perhaps being divorced or having a couple of long term relationships. Is part of his financial planning that he's saved a fair whack of cash but plans to top it up a bit by living with a woman who will be working for the next 25 years - a nurse with a purse - securing his financial future and making sure he has someone to care for him as he ages.

I think if it were me, and bearing in mind I'm late 40s and don't want children, I'd date him and have fun with him and see where it went.
But as you clearly want marriage and children I think you should probably throw this one back and look for someone else.

My SIL was like you from about age 37 and scared all potential dates by being baby and marriage obsessed. DH said he would have dodged any woman who was planning on marriage and babies so soon and told his sister it was best to see things develop more slowly. She chucked an absolute strop so he never said anything about it again. It was after she revealed she had asked a guy in week 3 of dating that she wanted to try for children in a couple of months.

There are people who retire early, I know some. One was a corporate lawyer and the other is a friend who received a huge share of his Uncles very large estate. Others made very sound investments. None of them are single though.

If any of my friends came to me with a tale of either of you as a date I would consider both him and you as waving red flags.

He looks good "on paper". Maybe you should get your accountant and lawyer to draw up a list of pertinent questions ? A couple of coffee dates isn't enough to be thinking about whether he's marriage material or not and tbh you sound like you're on a mission...or maybe using the same method as choosing a new car. Do you want a mate ? Or a fwb housemate ? There are so many considerations that shouldn't be transactional.
Get to know him, chemistry can't be faked , although it isn't always instant. If it's not there one of you will eventually meet someone they do "spark" with.

Just ask him if he wants kids if this is what you want. I'd be surprised if he did.

As loads of other PP have said, you need to ask the question around DC quite soon. There's a strong possibility he will say 'no'

If he says 'yes' there are a load of other questions you need to ask next.

I think the DC will be the barrier

Has he got children already?

I would think moost people at 50 years old wouldn't want to start a family.