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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:
LovedMyLastNameItHadToGo · 14/12/2023 09:31

i think OP you’ve got in your head family/kids and what YOU want, he sees someone 10 years younger than him he’s just going to have a good time with.

It’d be very pushy of you to start asking questions about his income etc that you want kids etc right now! He’ll run a mile!! I wouldn’t blame him.

Step back, stop seeing him as a sperm donor! Just think about what you’re asking us and what you want from him. I’m sorry it’s madness!

Vuurhoutjies · 14/12/2023 09:31

I know a number of men (all men, obviously. There's a WHOLE conversation there) who either could or have or plan to retire by 50, including my oldest friend and a number of his friends/colleagues. What most of them have in common is that they started out in professional jobs straight from uni (accountant, IT, banking etc), bought property before the housing boom and have worked consistently in well paid jobs ever since with no breaks. They're all between45-50. I also know plenty of ex-bankers etc in similar positions.

OP your biggest issue is that the chances he wants children at 50 with this relaxed lifestyle are slim.

I don't think you need specific questions. If you date, it will become clear what his priorities are.

Olika · 14/12/2023 09:32

If you want marriage and children then that has to be discussed asap as in a topic if he wants those things as you don't have time to waste.

knit1pearl2 · 14/12/2023 09:36

Britpop123 · 14/12/2023 08:10

Probing someone deeply about how they got their money, where it’s invested, whether that’s acceptable to the op, huge red flags and I’d advise him to run

at this stage it’s none of your business

I agree with this! Obviously you have to be alert to red flags but it's totally reasonable for someone doing online dating to be vague about finances if they're wealthy.

I'd focus on finding out more about how he spends his time as he doesn't work @lovelivesherenow .

FWIW, I am on dating apps and also play the lottery, I often wonder how I'd go about dating if I won the jackpot Grin

Northernsoul72 · 14/12/2023 09:40

If its only been two coffee dates I wouldn't even be thinking that far ahead. He might not turn out to be your liking anyway or vice versa. Give it a bit more time before thinking too deeply

HundredMilesAnHour · 14/12/2023 09:43

MyFirstLittlePony · 14/12/2023 08:08

I know quite a few men like this

they typically are landlords with a buy-to-let portfolio they started about 15-20 years ago

they can then play golf/tennis most of the day

one of them has a younger partner who he had a child with , so he’s now 60 with an 8 yr old

he spends a LOT of time at the tennis club, avoiding child care, but otherwise all seems well

Exactly! I have a 52 year old friend exactly like this. Owns a few properties and lives off the income. Spends most of the day (a good 4 hours every day!) in the gym. It baffles me that he seems to need no intellectual stimulation whatsoever.

He's a decent guy but very set in his ways. He'd be a nightmare to have a relationship with. Even as a friend he can be a pain at times due to his gym and food obsession. Was in a serious relationship with a woman 15 years younger but they eventually split because she'd had enough.

minipie · 14/12/2023 09:43

Agree the main question is kids

If he’s retired early then he will have done some significant financial planning and modelling (if he hasn’t then run away!) and I very much doubt kids were planned into that. So unless he is super loaded, having kids would require him to go back to work and/or become a rather frugal SAHD. Unlikely to appeal.

Crap1979 · 14/12/2023 09:56

I think the money is the least of the issues here. I would be looking for men younger than 50 if you’re aiming for kids to be honest. Men’s fertility health decreases from around this age and to be frank it’s old to be looking to begin a relationship view a view to starting a family. I think looking for men in this age range is likely to match you with men who are not wanting/already have kids (the kids are probably also not that young if they’re in their 50s). I’d filter your search results for men who are 35-45 or something like that. If kids are your priority don’t prioritise a wealthy man if he’s not looking for the same thing as you. It’s very early days though.

SleepingStandingUp · 14/12/2023 10:00

lovelivesherenow · 14/12/2023 06:41

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.

Show quote history

Does he want kids op? Honestly, at 40, him a decade older, I'd also make that a priority question. Make it clear what you're looking for because if he doesn't , it really doesn't matter how solvent he is.

Financially, does he own his own home or rent out mortgage? Does he see this as a forever decision - to never work again? And if he confident he can live a fully full and independent life like that for 40 years?

Daisies12 · 14/12/2023 10:01

Seems unlikely he'll want marriage and kids, assuming he has a large amount of money/assets, I'd be surprised he wants to risk losing half in a divorce. And kindly, given your age, I hope you are more than aware than biological children are statistically unlikely.

BeeDavis · 14/12/2023 10:04

You want kids with a man who’s 50 years old?

NoraBattysCurlers · 14/12/2023 10:06

The number of people working 9-5 jobs who can save enough to retire at 45 is so small that it is practically non-existent.

Yes, there are men who stop working at 45 and have enough saved to see them through 5+ years. But these men then need to find another source of funding.

The solution to their problem is often to find themselves a 40 year-old partner with a good job who can keep them in the lifestyle to which they have become accustomed.

IncompleteSenten · 14/12/2023 10:07

Basically you want to know how much money he's got and how he got it and possibly what that means for you if you were to be in a relationship with him?

I think it's a little too early for you to be thinking along those lines. Enjoy dating him and you'll find out more about each other naturally.

adriftabroad · 14/12/2023 10:08

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.

Yep.

Also, Is he married?

PropertyManager · 14/12/2023 10:11

I'm a man who quit work at 40, technically I still do work, but I only do the odd day when i want to of actual work, the rest of the time is just managing my property portfolio and business at arms length, I no longer need to be on hand if I don't want to be.

Now, fortunately for me I'm very happily married, so not on the dating scene, but if I was it would be a massive red flag if a woman started asking me about finances early on.

I have a good mate who, like me has jacked in the 9 to 5 having worked in the city, made a small fortune and invested well, he's single and dating, but his point of view is "look, i'm secure, I can afford what I want" and he's concerned the other way round, he wants the woman to be secure also - unfortunately there are gold diggers out there to watch out for.

So if you like this guy OP, I think you need to get to know him better before delving into his tax returns, or he might bolt!

HeraSyndulla · 14/12/2023 10:12

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?"

Totally agree with this and if he has significant assets to his name he would be insane to get married. Also somebody , who you’ve only just met, asking searching questions about personal financials is a 🚩 and a big one.

RudsyFarmer · 14/12/2023 10:20

For me work ethic is a really important personality trait for a mate. Im
a grafter and the fact that my DP is also, means we have two kids who work hard also and it kind of unites us all. I know people who took early retirement and they waft about like leaves in the wind. Kind of woolly individuals who pad their lives out with pointless endeavours. It’s a no from me unless he wax a millionaire and we could live some fancy life together.

PuzzledObserver · 14/12/2023 10:21

I think I would establish whether he has children, and whether he is open to having any (more).

If it’s a No on that, then his finances and how he spends his time are irrelevant.

The risk I suppose is that he might lie in order to keep you if he likes you.

GreatGateauxsby · 14/12/2023 10:21

@persimmonicelolly
Yes! This is obtusely what I was getting at.

If he is FIRE you'd do well to proceed with caution OP... Tight doesn't begin to describe half of it.

I looked into it and couldn't even get on board with FIRE "lite".
I would describe myself as sensible with cash, like to get the best price and generally make considered purchases but it was too scrimpy and miserable.

Britpop123 · 14/12/2023 10:21

BlockadeRunner · 14/12/2023 09:26

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.

What red flags is he waving?

Folklore9074 · 14/12/2023 10:21

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.

But to give him the benefit of the doubt, if he is just living off previous hard work and good money management then I reckon there are probably some significant lifestyle choices that he's made to allow him to do this. Are these compatible with what you want? At 50 I would think it is unlikely that he won't want children.

My advice is keep it light but, let it fail fast if it seems that your life goals aren't aligned. Trust your instincts.

JoyeuxNarwhal · 14/12/2023 10:22

"Are you solvent or are you expecting to sponge off me?".

It does happen that people are financially secure and not in employment but I think you're right to be cautious. I'd think twice about starting a family with someone that age too. Dh is 50 and there's no way he'd manage the newborn stage now, it was hard enough in his 30s!

Fraaahnces · 14/12/2023 10:22

Does he live independently or with parents? Has he lived with l/t relationships before? When? What happened? (Beware the man with “crazy” exes. We all know what causes that.)

Deathbyfluffy · 14/12/2023 10:25

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?

Why does it sound dodgy? One of my best friends did really well out of his company, sold it when he was 40 and now lives off investment income (rentals, a couple of holiday homes and general investments).

If 'having freedom' means 'dodgy' then society really is doomed!
I'm always jealous of the amount of time he has to chase his hobbies and volunteer.

BlazingJune · 14/12/2023 10:27

Too little info @lovelivesherenow

You need to know more about him!

If he's a multimillionaire, that's one thing, if he's pretty skint and is on benefits to supplement any savings, that's another.

After 2 dates I'd have asked how at 45 he was able to give up work and retire.

You say you want children.
He's 50. Does he?

What's his back story?

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