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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:
GonksAreNotJustForChristmas · 14/12/2023 11:05

BlazingJune · 14/12/2023 10:28

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.

Show quote history

Young children are hard work though. I think most people wouldn't want any at 50 years old. We have our Grandchildren but happy to hand them back. My DH was 40 when I had our child (I'm younger) and I think that was his cut off age. I'm his 2nd marriage.

Perhaps OP could date someone her own age.

purplecorkheart · 14/12/2023 11:08

As others said that whether he wants to have kids or not is going to be the first question that you need to ask and also if he does is he happy to give up/limited his time at his hobbies etc to be an active parent.

ilovebrie8 · 14/12/2023 11:08

You need to know more about what he did previously, it is fairly young to do nothing.

How does he fill his time/spend his days?

If you are out working it could be tricky as he is home and you are out working if you lived together...

Am not sure he would want to start a family, yes he can and people do but if he/s been driven in work and retired early he may not want children now he is retired...would he have the money to support a family? How much does he have saved....

I'm not sure his would work....just my gut feeling...

SarcasmAndCoffee · 14/12/2023 11:09

Does he have assets or investments?

Nonimai · 14/12/2023 11:10

Just take the time to get to know him and you will get a clearer picture - possibly not the full picture but who knows. Things like, does he tip? What are his views on charity giving? Does he own his house outright? Value? Does he employ help in his house ie cleaner? Gardener? Occasional decorator? Does he holiday? Where and how often? What are his hobbies, are they outdoorsy? What does he spend his time doing? Is he living off his private pension yet or investments. Is there a private pension? If he says he has investments ask him for advice for you, see what he knows. What was his job? Is there a health issue? Payout?
If he is financially secure and genuine he will also be trying to subtly find out your circumstances in the same way.

Zippedydoodahday · 14/12/2023 11:12

You can't really go round asking him about his finances two coffee dates in. It will make you sound like a gold digger.

Fourfurrymonsters · 14/12/2023 11:12

With respect, the guy is probably thinking that he’s had a couple of nice coffee dates with a woman, who being 40, isn’t really interested in having kids now. As PP have said, he’s 50 and enjoying a very nice lifestyle however he’s come by it. He’s very unlikely to want to be delving into the world of screaming bairns and dirty nappies. I certainly wouldn’t be.
If you want marriage and kids at this point, you’re likely going to have to date much younger men.

SamW98 · 14/12/2023 11:13

I actually know someone who is late 50’s and inherited money in his 20’s, purchased several houses in a university town that he rents out acacias never had an actual job since.

He gets a good income from the properties but he’s spent his entire adult life just playing about with various small projects, getting bored and moving onto the next one.

Afaik he’s on his 3rd wife and has several medium term relationships inbetween. Hes just never had a purpose and been settled.

hsapposhit · 14/12/2023 11:13

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!

Sensible post and you make good points about avoiding gold diggers and people asking too soon about the finances.
But as the OP wants to have children I think it's important for her to tackle the question of whether he wants children at all very early on so that she isn't wasting her (and his) time if he has already decided children are not part of his life's plan.

furtivetussling · 14/12/2023 11:14

Gillypie23 · 14/12/2023 05:33

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

By the same token, you don't want him thinking you are a gold digger and are only interested in him for his money.

beatrix1234 · 14/12/2023 11:15

Turned out the man didn't want marriage or kids, he was just looking for a friends with benefits situation and all this thread was... for nothing, jokes beside this is a possible scenario. I always think it's just funny when people would rather ask a bunch of random strangers on the internet that to the person in question.

pontipinemum · 14/12/2023 11:18

I think the most important questions you need to be finding out are if he wants kids/ marriage. Sorry to say but at 40 time really isn't on your side everything could go perfectly or you could be like me who at a decade younger took 4 years to have DS (absolutely no medical issues know just unlucky)

CharlotteRumpling · 14/12/2023 11:19

V few 50-year-olds want kids, I think.

beatrix1234 · 14/12/2023 11:35

CharlotteRumpling · 14/12/2023 11:19

V few 50-year-olds want kids, I think.

Or marriage! Specially if he's retired, he's not going to want to share his "pot", or he may have grown up kids and no intention to start changing diapers but would rather go and play golf (?). Or maybe he's an avid wanna-be-father wanting to breed asap, but if that's the case he would be looking for a much younger and fertile woman, not one in her 40's.

Seaweed42 · 14/12/2023 11:36

Does he own his own house outright?

Well, saving money for himself is one thing.
He can control that.

But what about if he's asked to contribute to a house and family?

To me it sounds like he's go no ambitions in life other than to avoid challenging himself.

I get that yeah give up horrible job but most people want 'something' from life other than tootling around coffee shops, the cinema and art galleries. Esp at age 50.

He's saved up money so he can live off that frugally and avoid responsibilities.

He can to to museums when he's 65.

Does he do any voluntary work?

What does he want from a relationship long term? I think that's a question to ask. He's on the Dating Apps for a Reason.

Now some public servants retire at 50 because they might have started work at 18 in a place. Especially if it's a very stressful job like A&E nursing or prison officer.

Has he a good pension?

Original poster
lovelivesherenow · 14/12/2023 11:37

Biffatcrafts · 14/12/2023 09:09

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.

Thank you for your advice.
You seem to understand why I'm keen to ask the right questions to work out his values. I want to know whether he'd make a good partner and father if he chose to be one.
I'm not sure how some here have arrived at the conclusion that I'm a deranged gold digger.
I've asked for advice, not abuse. Thank you.
Of course we both said we want marriage and kids (he has none) otherwise why would I go on dates with him considering my own desires? But at the same time, I have to keep it light so it doesn't come across as judgemental or nosy.
My hunch is that I have similar or more in asset and savings than this gentleman does. I just choose to work! This is my first encounter with a non-working adult so shoot me for wanting to ask the right questions to work out whether he can pull his weight if we were to build a life together as I will certainly continue to work and he may not.
And yes, I have my eggs frozen and a plan to do it alone within a timeframe so I'm not as desperate as to marry the wrong man.
But there's no harm in going on dates and seeing where that leads.

OP posts:
BrimfulOfMash · 14/12/2023 11:39

I wouldn’t quiz him about his finances, I would be honest about your relationship objectives.

Next date say you are enjoying his company but you are dating because you are looking for a partner to settle down with and hope for children, so whilst obviously you don’t expect him to be able to predict how your meet ups will go you would like to know for both your sakes if ultimately that would be what he is looking for

EmmaEmerald · 14/12/2023 11:40

I'm hoping to retire at 50 but childfree, live in a tiny flat etc

Live more frugally than friends and family
got a small amount when parent died

Does he know you want kids? What sort of property does he live in?

I was never a hedge fund manager or anything! If he was, I can see how he'd do that. I had a finance contact with two kids and a dog, left London, has a nice house in the south west countryside. And she even had to pay her leech ex husband some money. But she made a huge amount in finance up to age 35, so do-able. Because that huge amount was well invested.

If he wants to be SAHP, you might find it works really well. But question 1 is always, are they telling the truth. I would ask "how did you achieve that". But I've never dated online.

PullUpPrince · 14/12/2023 11:41

My parents both retired at 50 with a careful pension plan and investments that require little management. They’re just careful with their money. I don’t think this is that outlandish. It would drive me mad though living with someone who is able to be so laid back.

EmmaEmerald · 14/12/2023 11:43

x posted
you think you have the same amount at 40? Impressive.

Mirabai · 14/12/2023 11:44

If he was ex hedge fund and a retired with a massive pension and investment portfolio, ok. But it’s more likely that he has low standard of living and is super frugal.

Mirabai · 14/12/2023 11:47

…And he’s looking for a woman to bankroll him and provide 50% contribution to a property. He may have enough to feed and clothe himself but whether that’s sufficient to provide for wife and kids, even with wife working FT, is another matter.

Rec0veringAcademic · 14/12/2023 11:54

I had one of these. Funny and interesting at first, turned out to be tighter than a duck's arse and boring as ditchwater. Don't waste your time, no matter how badly you want a family.

Original poster
lovelivesherenow · 14/12/2023 11:56

HopeAllOK · 14/12/2023 10:43

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

Thank you. I appreciate it.

OP posts:
CharlotteRumpling · 14/12/2023 11:58

Oh sorry, you have updated that he dies want kids and a family at 50. But why? 😉

I just find it quite hard to understand why anyone would want to upend their lives at 50. I don't think you are a gold-digger though.

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