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Original poster

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

296 replies

lovelivesherenow · 14/12/2023 04:49

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?

OP posts:
CurlsnSunshinetime4tea · 14/12/2023 05:02

Since he’s not in formal work how does he spend the day? How does he stay current/relevent in life.
How did he earn the funds, how stable are his investments, how much attention does it take to manage his funds.
How future proof are his investments.
Paying attention to finances can be all consuming, a red flag if he’s overly tight.

CurlsnSunshinetime4tea · 14/12/2023 05:05

Oh family, how involved are they. Beware the underemployed brother who leaches money from him (there’s usually a few leaches).

PieAndLattes · 14/12/2023 05:20

What does he do with his time? Is he solvent? He might not need to be loaded but I’d want to know he could at least feed and clothe himself.

Gillypie23 · 14/12/2023 05:33

Make sure he'd make financially sound. You don't want him living off you.

Soontobe60 · 14/12/2023 05:37

How old is he?
What work DID he do?
When did he stop working?

HalebiHabibti · 14/12/2023 05:42

Is he interested in getting involved with someone still burdened with work?!

Oddsoc · 14/12/2023 05:45

I’d guess he may have followed the FIRE approach which advocates extremely low spending. If that’s the case I’d ask about his lifestyle to check it is compatible with what you want out of life ( like how often you eat out, spend on clothes and entertainment etc). Mr money moustache is a blogger on this, if you read the forum on his site you’ll see the extremes some go to

determinedtomakethiswork · 14/12/2023 05:58

This sounds really dodgy! How old is he? What does he do with his day? Does he have any friends?

Does he have to watch every single penny? If you had a child together, would you have to go out to work and leave him with the child? Have you considered what would happen if you split up?

Bananalanacake · 14/12/2023 05:58

What does he do all day. As long as he isn't claiming benefits when he's fit to work I wouldn't be too worried.

Kittenkitty · 14/12/2023 06:04

Will he marry? He’d be risking losing money in a divorce.

Children - if you’re interested in children whether he can afford them.

CostedStrikeRate · 14/12/2023 06:06

What did he intend to free up his time for, if not conventional work?

supersuss · 14/12/2023 06:07

Are you dating for marriage or potentially also family? If he got out decades before one would, I'm guessing he/you are still at an age where having children might be on the cards. Will his savings be enough to support any potential kids?

Agree with PP regarding FIRE. Was this achieved through extreme saving that will continue throughout his life and could get quite frustrating? Or did he get lucky with shares in a startup that got bought out, in which case, is he managing the money or just burning through it? Perhaps something in between, e.g. City job with a few big bonus years and he was astute rather than tight? Each will have slightly different implications for lifestyle and sustainability.

Socialyawkward · 14/12/2023 06:12

I would ask him a few base questions to establish some facts - has he got enough to contribute towards a future with you? Where it slcame from and if he has anything still running ( investments ect ) but mostly I would be watching to see if his actions match his words.

determinedtomakethiswork · 14/12/2023 06:15

TBH, I wouldn't be interested. I wouldn't want to go out to work while someone stayed at home doing nothing. I wouldn't think that he'd have much to talk about and I wouldn't think he'd have any friends because so few people are in his position. I certainly wouldn't put myself in a position where, if we had children and split up, he had them living with him all the time because he was the sole carer.

Oblomov23 · 14/12/2023 06:20

How did your meet him? He clearly is out and about then? So he may have plenty to talk about. What does he do with his time? Is he generous, of heart, or that very unattractive trait of being tight? Some of those FIRE recommenders are almost obsessional and go to extremes to achieve the end goal, but as a passenger I'd find it miserable. Life is for the journey, not just the end goal.

Ggttl · 14/12/2023 06:21

It really depends on his age and what he does with his time. 9-5 jobs don’t generally earn enough to give up work. Did he inherit a lot of money?

LadyWithLapdog · 14/12/2023 06:28

I know one man who is “independently wealthy” in his 40s. He inherited and he’s been a lazy arse even before, in anticipation of said inheritance. He’s clever and pleasant, but a bit tight.

pilates · 14/12/2023 06:37

What are your ages?
What does he do to fill his days?
Does he live a frugal lifestyle?

Original poster
lovelivesherenow · 14/12/2023 06:38

I met him on one of the dating apps. I want marriage and kids.
We've been on two coffee dates but kept it light, so I haven't asked any hard questions and I haven't had a chance to see whether he's tight on significant spending.
He is 50. He stopped working at 45. He spends his free time doing hobbies such as sports, arts, going to events etc. I see he has a sense of curiosity and is in touch with the world and our conversations are great.
He is out and about (so he claims). It's just that when people go to work, he goes off to do things for leisure whenever he likes.

OP posts:
Original poster
lovelivesherenow · 14/12/2023 06:41

lovelivesherenow · 14/12/2023 06:38

I met him on one of the dating apps. I want marriage and kids.
We've been on two coffee dates but kept it light, so I haven't asked any hard questions and I haven't had a chance to see whether he's tight on significant spending.
He is 50. He stopped working at 45. He spends his free time doing hobbies such as sports, arts, going to events etc. I see he has a sense of curiosity and is in touch with the world and our conversations are great.
He is out and about (so he claims). It's just that when people go to work, he goes off to do things for leisure whenever he likes.

And I am 40.
His parents are still alive so I don't think he's living off inheritance. According to him, it's been a bit of hard work, saving and some good luck.
Perhaps inheritance from grandparents? I'd like to know how to get to the bottom of it by asking the right questions.

OP posts:
NeverDropYourMooncup · 14/12/2023 06:42

Just as likely on benefits and spinning you a yarn.

Tontostitis · 14/12/2023 06:42

He's retired. He's 50. Marriage maybe, kids are probably not on the cards he's retired early and likes his life. And I bet he's a bit older than 50.

redboxer321 · 14/12/2023 06:44

I think he's unlikely to want kids

HachiAndNana · 14/12/2023 06:46

I think your bigger issue is at 50 and independent with a great life doing his own thing, why would he want to get married - and definitely, why would he want to have kids? Irrespective of where the money comes from - and it's not inconceivable he can afford to not work - are you actually after the same thing?

As an aside two coffee dates in, I'd play it a lot more light-hearted than asking deep questions like "where's your money comes from?"

pilates · 14/12/2023 06:52

What @HachiAndNana said