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?

No, I do not have children. It's not a concern at all. There are multiple routes to motherhood. I'm more confident about being a mother now than ever before.

I'm not having a union with anyone if I don't feel they're right. And no man is becoming the father of my child if I didn't think they'd be right.

My date looks way younger than his age as do I. He is a lovely gentleman (I mentioned this earlier on) from what he's shown but of course it's early days so time will tell. He is kind to me and has a good loving family around him from what I'm told, makes me laugh, communicative and shows interest in me. He's not shown me otherwise so we will continue to date and I'm not going to be cynical as most want me to.

I've experienced enough men my age as well as older men with various red flags so I do not mind a slightly older man with a good head on his shoulder. I won't overlook a good man just because of their sperm quality. I will leave that to the doctors to decide. And I deserve a man who doesn't write me off because I'm 40!

My date comes across as mature, open, self-aware and knows who he is and what he wants. He volunteers and has social projects running in the background. He just doesn't work in the way that I do and would want to continue to.

I haven't come on here needing to be told what to do as some have highlighted.
We've been having conversations (not forced) before we met on what we want/ not want. We've met twice and he's shared some of his life with me, I have done more of listening and taking it in and asking questions but not prying much. He's asked me questions about my life and achievements and I have tried to share without going into too much detail.
He paid for coffee on both occasions and he's now planned a 3rd date which he's paid for without negotiating. This is the first date I've had in a long time that I've not had to pay in full or go Dutch even when all I've had is water.
There's an understanding I think that we're both financially comfortable.

But comfortability is subjective when two people combine lives on one income and a child comes into play. I therefore needed some ideas on how to ask some crucial questions without coming across as hard and some insight on other things to ask that I may not have thought of. For example, work ethic- if we had a business opportunity where we had autonomy, would he explore it for the sake of having more disposal income? Does he have enough in the bank to pull his weight for whatever we need/want without overthinking it? Does he have enough to pull his weight for private schooling? Has he thought about the implications for if he needed to buy a new property (since mortgage lending is typically dependent on earnings)?'

I think any child would be lucky to have me as a mum or sole parent. I come with love, wholeness, life experience, resources and so much wisdom to share.
For those who say they were ashamed of their older parents, I have no words.

I wouldn't take on other people's issues about older parents, short of not having kids (I have two or three friends who had their last child 40 plus), what are you to do about that, you can't rewind time. Late forties is fine to have a child for a man, a lot of men don't settle down til 40 plus either these days.

I know a few terrible parents (alcohol problems especially) and they are nothing to do with age, in fact, they tend to have children younger.

I think you are being very sensible with this guy and he sounds great so far!

You’re not looking for a partner OP, you’re looking for a sperm donor with a big bank account. Why are you not honest and just ask the guy to bring his bank statements on the next date? That will answer all your doubts and then you will know if it’s worth “investing” in a third date. Why don’t you ask him those critical questions (“do you have enough money to pay from private education”) Versus a bunch of strangers? I’ll answer the question for you: you’re terrified to be perceived by him as a golf digger and have him run for the hills but you can’t care less about a bunch of virtual strangers on the net thinking the same.

I don't genuinely think it is anyone's place to judge this man as being too old for kids. It is probably unlikely he does want them but he might do. FWIW my DH is in his 50's, works full time and our youngest is one. 😀

@beatrix1234

Here are some of your comments:
The fact you have opened a thread asking a bunch of strangers if this man can afford having a family (versus being honest and asking him) makes you look like you have a hidden agenda…
Historically, men have often married younger women and become fathers in their late 40s or even 50s. And they would choose young virgins (not 40 yr old women)…
She’s mainly looking for a pseudo sugar daddy that can support her having kids...

Who raised you or the lack thereof?
You're projecting your negativity, tackiness, and idealistic approach to life onto a 'stranger' on MN. So, I don't care what you think. You're a mean, unintelligent, and an unwise 'human' with a lot of experience to have and more growing up to do. Do keep your ugly thoughts to yourself^ and go elsewhere!
This thread is to seek advice from people with a pragmatic sense of reasoning, and you are clearly not one of such.^

100% this ^^ the guy should be seeing the OP as the red flag and he should be moving on

I think you're sensible in asking all the basic questions OP. You need to be happy you're on the same page.

But, and I say this kindly, I think you're completely misreading the situation.

He may be kind and considerate with a loving supportive family, but there's nothing so far whatsoever to suggest he wants to upend the life he has built by having children and getting married. He would literally have to compromise everything he has worked hard to build and risk his financial security.

And seriously, why would you want to risk your financial security? if you're richer than him, he could literally take 50% of what you have!

I think you're wasting time chasing a family setup that may never happen at the expense of being a mother. Having your eggs frozen by no means guarantees success.

Oh, give over OP @lovelivesherenow . I didn't quote your reply to @beatrix1234 to this, as i deem these 2 quotes as more relevant to what I want to add,

OP, you are forgetting you have asked a question which a few of us on this thread have real life experience of, and not just theorising. I posted days ago to be supportive- I answered your question. Whilst some posters have used some strong language to pass judgement on you, even I picked up some negativity coming from you which would look like a red flag to someone with the qualities you want: means to support himself etc etc aka someone wealthy.

Not to be crude, I dated when I had a brilliant career and just enough in the bank. I also dated when I was a millionaire. In between those two scenarios, I met my late partner who was a multi-millionaire but it was our values, common goals etc etc that brought us together as I had a few millions of my own by then. In fact, I was adamant, I didn't want to date him (and told him so) because I couldn't first see we truly had same values- all that revealed itself as we stayed in touch, and then we realised we were made for each other. Sadly, Covid took him away.

All I am trying to say is that, this update of yours I have quoted, really sounds like an afterthought ( I have no axe to grind as I did it my way and got what I wanted with my DH.) And the same thought that came to my mind (which left me disappointed as I had an open mind about you when you posted) was exactly what beatrix had posted: ' You’re not looking for a partner OP, you’re looking for a sperm donor with a big bank account.' It was too early so I decided not to post something that might upset you- I just feel it unfair attacking this poster on this reply, as I had teh same thought upon reading your reply.

If this statement is incorrect, you have a long way to go, to represent yourself correctly. I just hope this guy doesn't get the same feeling, as you seem to want this to work. Wealthy people can suss people out a mile off, and are usually well mannered they would just phase you out slowly after a few dates or even months of dating if they too enjoy your company, and then you wonder what happened.

And something else I wanted to share as part of my original post. When I was first semi-retired and single, I met this guy and we hit it off. Except, I don't know what happened as it was just not working- not making/keeping plans etc etc. He had an idea that I was self-sufficient, assets and have a well-paying career I can pick up any time.

Anyway, I was devastated, picked myself up and moved on.

Fast forward years on, he has confessed he made a huge mistake with me and 'was too cautious, and he now see he should have taken me at face value and accepted my wants' (his words). I was upfront that I wanted kids and a family.

I told him, he was not the first one to express similar sentiments once they realised what they lost.

So, don't get too hung up on 'investigating' the poor bloke- none of us has a crystal ball. But if you lead with your heart and open mind (hence most of us as emphasising personality, kindness, make you laugh as more important to start with), you will get all your answers about his finances without embarrassing yourself.

It sounds like you know what you want OP. You don’t need anyone else’s permission to date this guy. Just go for it.

Just answering your original post without reading replies etc.

I wouldn't trust it. My husband fed me a similar line when we met, and his messed up family backed up every word. It was only after we were married and 2 kids in did the truth come out.

Everything he told me was a big fat lie and his family backed him and lied to me for him for the shits & giggles.

He originally told me he had retired before 40 as he has made so much money, he was a company director and still kept his hand in ...... LIES!!!

I wouldn't trust what you're being told.

Oh, so sorry this happened to you. Yes, one has to keep eyes and ears open, and have faith. I live in central London where none can keep up a lie (those living with friends/ at dad's place etc will soon tell you they are moving out of London, when in reality they never lived there to start with etc) for more than 3 weeks, without you noticing, unless you are not looking- so I guess I have a different experience and was lucky. I purposedly also had my antennae sharpened from the experience of meeting so many bullshitters. Lot's of people there are in debt or living on overdraft or credit cards- living lifestyles they cannot afford. I was shocked when I first established this. But in the end, the fakes were easy to spot.

So, discovering 2 kids in, meant discovering 3/4 years after marriage. How did you discover the truth? I hope you are ok.

@lifestylee

Sorry of my message was quite abrupt. Our circumstances are different.

The same family member who originally tricked me and covered up and provided 'evidence' that my DH was legitimate, decided to tell me about the deceit a few months after we married.

The questions I asked were to see bank statements and his full credit file before I sold my house ... he showed me copies from a family member who shared the same initial and surname, I literally had no idea that anyone would even consider this level of deceit. I did attempt to do my due dilligence.

However it was all brushed under the carpet and I was gaslit by him and many of his family and made to feel in a constant state of confusion. Like I had made everything up to suit my own agenda, I was in a deep fog. I am coming through this now and attempting to figure out how to get out of my situation.

I guess it took me meeting those awful people to learn that people aren't nice, they'll happily take everything from an undeserving kind hearted person.

I watched the Puppetmaster on Netflix recently and some of the tricks that con man used feel very real to me.

Find someone who works, as one will always need generating income prefferably multiple streams for as long as they live.

This guy isn't suitable for marriage..nor a relationship

Why do you say that? The point of the thread is that some people have made shrewd investments that allow them to generate sufficient income to live comfortably without being employed. We don’t know whether this man has actually achieved that or not but people who have done so are in a much more secure position than those relying on monthly salary to make ends meet.

Up to you @lovelivesherenow but going for a man of 50 who 'retired' at 45 would not be for me. Even rich, successful, famous men/people don't 'retire' at 45. They still do some kind of work and keep active, and/or change what they do. eg, a sportsman/woman or dancer etc, would stop at 37-45 say, but would be a TV presenter or a writer or a trainer or something. They would not just do fuck-all.

I could never be with any man who just 'did nothing.' Sorry. I wish you well in whatever you choose to do.

I can see this working out really well, if everything goes according to plan. Potential DH is in a position to be there for the child, OP is young enough to have at least one child (nature willing), or adoption could be a route.

I think as the relationship progresses, the potential partner will start to tell you more about his life and his situation, and gentle enquiries about this should not be out of bounds to someone you may intend to marry.

Oh, you remind me.

I once met an artist who was a bit special (his parents supported him for most of his life) and they gifted him a one bed flat in a nice area. He also had another flat elsewhere which he rented out.

All fine. I had a 3 bed flat, wanted to work etc etc so I thought he could be at home with kids and help with homework. We mostly spoke on the phone. Lo and behold when we started messaging and emailing- he could not spell; had no grammar etc etc. That.was.it.for.me. as I did not see any use of him in my life. The idea I would work extra hard for the family and still do homework and God knows what else, was for the birds.

Wow! Thank you for sharing. I wish I could HUG you.

I can only say, I am soooo sorry this happened to you.

I lived in North London before I moved to central London where I worked- I was always into my studies and work, so i had to learn by observing others and from friends who were too kind to share their dating experiences. One use to say, I lived in Monaco, so I have seen it all- she too was savvy about her life as had family wealth. I was naive then. Thank GOD for those awful people I met/saw who only cared about themselves ( they were not in my life), that I decided to put myself as number 1 always. Sometimes I came across as a gold-digger but I did not care- I was protecting myself and did not need anyone's money/assets. It made me ruthless and helped me weed out lot's of them.

Gold-digger comment: it took me a long long time before I paid for our grocery shopping (100 or 150 a week) as wanted to see DH could really sustain his lifestyle without me. Made me feel awful, but I didn't want to cover up things too early. Dh said nothing. Whenever I now pay for our shopping, DH thinks I have done a big thing lol lol lol as he doesn't expect it. Glad it worked for me.

Yes, you will come out of this. You will come out stronger. Good luck.

@lifestylee

Thankyou for your kind words.

You sound so Stoic, Stoic is my new years resoluution!

I have had a very sheltered life in my adult years. My ex husband was very wealthy in comparison to my current husband, so some of the lines I was fed by my current husband and his family weren't even impressive, just normal if that makes sense? However for him, they were lies and he was bigging himself up hugely!

I'm so ashamed to be married to him truth be told. He punched me earlier this year as I wouldn't have sex with him. I told a friend, a cousin and 2 of my brothers that my husband punched me; all 4 of them said I need to go back to him as we have children together. So it's no wonder I fell for so much of this persons deception. When you have friends and family like that who needs enemies!

If you want this man for children, I'd advise you to think twice. If you want children, you really can just do it yourself through a clinic. You'd save yourself so much heartache!

Stoicism just whilst I'm readying myself to leave that is; not because I'm accepting a life of lies. Sad I have to play him at his own game for my own sanity / safety / security.