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?

Oh do stop being so small minded.

DH has a colleague who was divorced at 50, with adult kids, then married someone 15 years younger and they have two children of their own now and are very happy.

Rather than coming straight out on date 3 and saying you want children you could ask him if he has any. That way you can go from there. Yes he does, how old are they, is he done having kids. No he doesn’t have children you can then ask if he ever wanted them etc.

He must be very well off to afford not to work for the next (possibly) 40 years.

I'd be wondering is he's a fantasist and will need to work again. He'd need a couple of £million to live comfortably for 35 years.

Some of 50 who doesn't need to work must surely expect questions about 'how come'?

If he's genuine, he'd be saying he made a mint selling a company, on the stock market, property, whatever.

I assume as you met online that you have already filtered the men you meet and you yourself say in your profile that you want a serious relationship and children.

If you don't say that, you're wasting your time with men who aren't on the same page.

I think you are right to be a bit suspicious. The claim that it was 'a bit of hard work' to save up enough to sack work off forever sounds to simplistic to me. There must be more to it thank that because if it was simply a bit of hard work then more people wouldn't work past 45.

I think it's totally reasonable to be vague and a bit simplistic if you are wealthy when an online date you've just met is questioning you! @Folklore9074

@lovelivesherenow Focus on getting to know him as a person and whether you're compatible. Once you've done that I'd focus on understanding whether he wants kids and marriage.

To go in all guns blazing about babies and finances is not emotionally healthy, I do get it though (am in my 30s and also dating with the intention of marriage and kids!)

. Once you've done that I'd focus on understanding whether he wants kids and marriage.

Most women of 40 who want those things say so in their online profile.
They've not got time to waste.

If they don't they are wasting their time and their dates.

Where has OP said she wants children? A lot of assumptions here from people who clearly assume marriage and children always go hand in hand.

I don't think being retired at his age is that wildly unlikely? He might have had a windfall, or worked hard at a high pay, or paid off his mortgage. If he prioritised early retirement (and hasn't been married/had kids before now- do you know this?) then I think it's entirely possible.

If you want to get married then I don't think there's any point beating around the bush, just tell him that. Assessing him like he's a used car won't get you anywhere.

It's entirely up to him how he lives his life.
I know someone similar and he is one of the happiest people l know, he lives a simple way of life but it suits him, never married, no children, has many hobbies.
We are very conditioned from an early age to believe there is one one route to take in life, literally work yourself to death. Some wake up and jump off the never ending treadmill.
If you are looking for a husband and children this isn't your man. He doesn't want to be trapped, he is a free spirit.

I know loads of people who stopped working by 50. All single men
Bought property in London in early 90s- professionals. Piled cash into pension. Not married. No kids

Sold up and moved to country and live outdoor lifestyles mortgage free with £300k in the bank to last them until 55 when they can start a pension drawdown. But most will inherit most likely around then as well

He sounds like my 52 year old brother. He lives very frugally. He doesn't spend money on activities/christmas or birthday presents. He eats the same cheap meals and sandwiches over and over. He loves not working, but has become very lazy and tight. He conserves his petrol usage which affects the things he does. He always appears wealthy on dates, but soon reverts to his miserly self when they move in. They never last, as he never wants to go out and spend money. The girlfriend ends up funding everything, before wising up. He pays nothing towards his children, apart from a monthly food shop from aldi. My advise to you, would be to end it. Choose someone who has a job and money coming in..

OP said she wants children.

The OP I want marriage and kids

@sweetpickle23

But surely you want to make sure he's someone you'd like to have kids and marriage with rather than your only criteria being a man who's up for it?

As in my PP, I say this with the perspective of someone dating for these things and also don't have a huge amount of time to waste!

lol thank you- I re-read her posts about ten times and somehow missed that!

In that case yes agree even more that you need to get on with it and tell him what you want.

He was probably in a high paid job with a good pension and retired early. When I worked for a Ftse 100 company they liked to retire their directors at 50. My own parents retired at 50 with good pensions, so 45 isn't much younger. Does he live well, does he own a home and car etc?

Being blunt, after 2 dates you don't know he is a lovely man.

And just to correct some posters, he's 50 now and stopped work at 45.

That is very young indeed.

@lovelivesherenow You need to be ruthless. You are 40. If you want children you have maybe 4-5 years max. You need to make it clear that you want marriage and a child, and not dither about. His income isn't so much the issue, as how he wants to spend the rest of his life.

That means with kids or not.

I really feel for you. The replies fall into two camps, basically saying:

• You can’t be asking him about the big things like kids and finances this early on. It’s none of your business at this point and you’ll just scare him off.
• At 40, you have no time to waste and need to cut to the chase with this stuff pretty quick.

Unfortunately both are true. Nature really is very cruel to us as women.

You may not be ready to go there yet but I can tell you from personal experience that donor conception offers great options.

Wishing you all the very best wherever things take you. xx

My own parents retired at 50 with good pensions, so 45 isn't much younger.

Those days are over unless someone made a mint. Or worked in the public sector and you can't retire now at 50 on much of a pension. (except maybe the police.)

Not many people can access pensions now at 50.

You're talking about the few top CEOS of multinationals who earn £millions a year.

For me the biggie would be mental health. Someone I know is in that situation. At first, it was all about being lucky enough to be able to go without working for a while. Not untrue, but the non-work was mostly about mental health, and the money that enabled not rushing back to work might well have been part of problem, because the purpose and routine that a job provides are often good for mental health. After a while out of the workplace at that age, it's virtually impossible to find a suitable job, so it's not an easy decision to reverse.
I'd find it very hard to be truly happy to be with someone who didn't have purposeful activities while I was slaving at work. If non-job means working hard in unpaid charitable activities etc, great, but I think I'd struggle with someone having fun doing their own thing all day and get very naggy if they didn't do all the housework. Which wouldn't necessarily be fair if they're pulling their weight financially. But emotions would get the better of rationality in those circs for me, I think.

I do know one or two people who have done this, all worked in the City.

However, these type of people are often very driven, and my experience is they tend to then set up companies and do businesses, just for 'fun'. It's kind of odd he's just pottering around doing hobbies and perhaps suggests a different route to his retirement (inheritance, not needing much money?)

The only way (I always tell my girls this) to know someone is to see them repeatedly over time, observe their behaviour, how they are with their friends, how they treat other people. If you are alert, you will pick up anomalies, or things that don't sit right, or that he's not got any friends or whatever- including about his business affairs. I would not ask outright, but as part of getting to know him better on every level.

I absolutely would not be cross-questioning him on a third date about his finances, that's not your business, and it's up to him when and if he discloses all that, I suspect he wants to find someone who trusts him and doesn't see him as a meal ticket, and that will only happen if you genuinely get to know him and like him for who he is. Your biological clock is not his problem at this stage- and I think you just have to accept that unless you want to take a giant risk and end up in hot water with a baby and no great husband, then it will take a few months, or even a year or so to work this out.

He sounds ok so far, but don't cross-question him, find out if he's fun, reliable, has good friends and family, has good values, if you don't know these things you don't know him and you can't then assess whether he'd make a good partner. All women on the Relationships board trying to get out of financially abusive or DV situations probably felt the first two dates went well, it's over time that people's true nature is revealed.

My friend is in his 50’s and retired around 10 years ago. He purchased 10 houses in his 20’s and lives off the rent.

Has your guy been single for a while op? Does he have his own dc? I know a few single men in their 50’s and they have all been single for quite some time and find it hard to keep a relationship going, I think this is because they have become so set in their ways.

I’m 50 and would hate to have babies at this stage of my life and can’t imagine any of my male friends of the same age wanting the same.

I also agree almost no-one can retire at 50 now unless they have an inheritance or big jobs. Not in the public sector- 55/60 may go part-time, but soon you will be able to see where he lives and how he runs his lifestyle and that will tell you what route to not-working he has taken. Most of my friends in professional jobs cannot afford to retire in mid-fifties.

The not working isn’t a big deal, as most of us would retire early if we could.

The issue is that most people at 50 don’t want babies and maybe not even marriage, so these are the questions I’d be asking.

The trouble is though that he can promise you all of these and not actually mean it.

I would go on the third date and ask him what his plans for the future are and if he’s looking for something serious with kids and marriage.
Try not to say your opinion on these things first as it may sway his answer.

I'm older than this man.

The only people who are younger than me who could retire very early have made their money in the City as investment bankers, or as CEOs involved in company sales where they have equity, or people working in venture capitalism, or business owners who sold the business on.

To live comfortably, without working at all for 35-40 years, you're talking of at least a couple of million, bearing in mind inflation for 35 years.

He may have that or he could have bought his home for peanuts (you can / could buy houses for under £100K in the north) .

To live a basic lifestyle, on a pension, FAs say you need around £25K if you want to do anything other than sit at home.

You will soon learn what his life involves.

But for me, what someone does - or did- for work is very important. I can't imagine just accepting someone saying they retired at 45 without asking how.

Well since he has no means of making money, I'd ask if he was expecting you to have a large dowry in the eventuality of marriage?

Also does he have enough money saved up to last him from whatever age he is now until pensionable age at 67?

You also need to try and find out what his monthly budget is? Which will give you some indication of the type of life you'd have together. Obviously, if he's on a tight budget you won't be having many meals out, holidays, gifted Cartier diamond bracelets, etc.