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?

@lovelivesherenow What a culture we have these days. A man is allowed to meet a woman and initiate casual sex even on a first date, but a woman who wants commitment should pretend she doesn't at least for a while.

There's absolutely nothing wrong in wanting a committed relationship and absolutely nothing wrong in wanting sex on the first date, I was on OLD for a long time and saw lots of people stating in their profile they were looking for a serious committed relationship, no stigma attached to that, but what has commitment has to do with money in the bank? The guy can have tons of money but he may end up not getting commited. Also you don't know this man from Adam, it's been two coffee dates, you may end up not liking him (or vice versa). The only way you're going to find this is by dating him, getting to know him and trying to find out about his finances. It would be easier to go on a first date with your bank statement (lol!) but things don't work that way I'm afraid.

OP I understand your concerns and also very well the FIRE lifestyle (have been a blog reader of Mr Money Moutsache, etc) and admit the issue is a difficult one. Should you give up work earlier rather than later, etc. I think you want to see someone "engaged" /curious with life in some form: giving of themselves to the community and their family etc whether that be paid or unpaid. How is HE engaged with his community and how will that play out with you? You want to see some "matching energy" from him I think.

@EmmaEmerald I am sure to some extent it's on the eye of the beholder, but that was how I felt whenever I dipped into those communities on say Reddit. I also felt there was a lot of overlap in posters in other negative-vibed things. It might be that Reddit is just a fairly hard place in general (I never used it much for anything except financial advice).

In any case, no, it's not me reading in the media about the movement, it's me following the movement for several years with great interest. And as I said, we got a lot out of it in terms of how to organise our finances (invested early, and I guess got ourselves to BaristaFIRE quickly then had kids and as a result can now have an excellent lifestyle on one wage in a big capital) but I felt the focus was terribly narrow. Kids? Expensive. Expensive hobbies? A waste. Wife wants a big house? House poor. Like, what is life FOR then? Also, the few friends from uni that I had that were overtly interested in FIRE hadn't figured out what they wanted with their life and had this attitude of "but if only I were free". Truth is, they still wouldn't have known what to do with their life (and they still don't, years later).

I am genuinely glad you have found a part of that community that isn't like that!

but what has commitment has to do with money in the bank?

I know that finance is not some women’s strong point, but the question is can this man who says he’s looking for commitment and kids actually afford them - or will OP end up bankrolling him? He’s not working - it’s a totally legitimate question.

You are dating with the goal being marriage. You may find that someone with considerable assets will not entertain the legal contract of marriage, and the risks that go with a future divorce. I am financially independent from property dealing, wise spending in my youth, large inheritance and business investments. I would not marry, ever. I don't agree with it for starters, and I wouldn't even marry someone richer than myself. I did it once with a prenuptial agreement when I was much younger and not so financially secure. I would not do that again, and have had three relationships fail over the past 12 years due to a refusal to marry them. Of course, this is just me, and my risk adversity over losing money to a marriage gone wrong. If you like him, date him and have some fun. Don't base that decision around if he has money or not. It takes a long time to get to know someone and enter that phase where marriage would be discussed. While you have every right to expect marriage, he also has every right to not want to go there. In the meantime, if you like him then get to know him more and keep your options open. I would just say enjoy spending time together and the issue of his financial position will probably come out naturally.

And you think a bunch of strangers on the internet who don't know the guy from Adam can answer that question? The only way to figure that out is to ask him, if the OP feels that's too intrusive she's going to have to date him for a while and figure that out for herself. She might even discover that he's stingy, has a bad breath or he's blatantly lying and just wants to get her in the sack, who knows. We all wished we had a glass ball.

Eh? Where did I say anyone on this thread can answer that? Of course she needs to find out from him.

Lots of us have said "be direct". I never wanted kids and said on the first date or before! (though annoyingly some didn't believe me).

@WonderingAboutThus oh my god, no, most them have kids and hobbies. We met ages ago when FIRE was a bit niche, didn't have a name even, and I'd bet money most of us aren't on Reddit. I'm probably one of the youngest ones there, so many have hit target - but certainly there's people who kept up hobbies all along.

I admit, they sometimes get a bit closed minded about investment choices but I never regret asking them for advice. But tbh I think most of us would find Reddit a bit scary.

I didn’t say you said that (apologies if my wording was not the best), I just wanted to
emphasize the fact nobody knows this guy and if he has money or not. He could be a secret millionaire or he could be on a tight budget. She’s going to have to figure that for herself by dating and getting to know him.

From experience of a slightly younger non-working male

His lack of a 9-5 (but plenty of money for what he wanted to do) was directly related to the number of hidden cameras he had set up & the revenue he gained from other perverts paying to watch the women he was covertly filming (in both his home & theirs)

Not the usual route to retirement and if it had been suggested that was what was going on at the time I met him I would have never believed it of him

Yet that indeed was his method of financial freedom at an early age

No idea how anyone is supposed to protect themselves from a man so determined to abuse women to feather his own nest but being very very cautious about one without an obvious source of legal income would be at least a start

That guy is a criminal, simple as, but that doesn't mean this one is a criminal too. If I were a curious cat like the OP I would continue dating the guy, see if I like him, and maybe towards the 5th date bring the money conversation casually, tell him that she's interested in investments, ask him for "financial advice" and slowly pull the string and ask him: so how did you manage to retire at such a young age? tell me your secret as I've been recently into FIRE (or whatever that means) and get him to open up about his own finances. I would make it look like I too am looking to retire and would love to get some advice into how to invest my money.

Just the thought of the poor man attending a secondary school parents evening at almost 70 let alone the poor kid’s embarrassment. It’s not shallow, it’s a very real fact.

The above scenario won’t be easy for you either as a mother fast approaching her 60s.

If you haven’t already, it would be prudent to educate yourself about potential genetic issues caused by having children very late.

Who knows you might be lucky, but you might also find out the hard way that the biological clock (his as well) is there for for very good reasons.

Mine had me in their early/mid 40s. They were too old. Completely out of touch with the youth of the day. It was frequently embarrassing. I loved my parents but by high-school people assumed they were my grandparents.

Not saying it'll be the same with everyone in their 40s, especially not now adays woth social media etc... but I wouldn't deliberately do that to a kid after my own experience.

They could only have one as they had me so late. Which suited me fine but... you're a wee bit mad if you think you'll have a good chance of 'kidS' plural. Assuming you have one at 43/44 (sensible timeline to get to know him and accounting for a year of trying and another year of pregnancy) Do you really think you'll be up for another at 46? Unlikely.

Also, a 50 year old man who has never had kids...probably doesn't want them. If he does, he certainly isn't going to want to do the bulk of the parenting as he's only having them out of fomo.

Just the thought of the poor man attending a secondary school parents evening at almost 70 let alone the poor kid’s embarrassment. It’s not shallow, it’s a very real fact.

The above scenario won’t be easy for you either as a mother fast approaching her 60s.

Looks like you need to go back to school to help your own maths @AndOnAndOn1000

Having a child at maybe 41-42 means the parents would be early 50s when their child was a secondary school.

But far worse is the disgusting attitude of (I assume) youngish people who who seem to have nothing but disgust and prejudice about older people/parents.

What has our society come to when age and wisdom are no longer appreciated?
When someone older is scorned and written off? Seen as an embarrassment?

Historically, men have often married younger women and become fathers in their late 40s or even 50s.

How disgusting to say that a child should be embarrassed or ashamed of having an older parent.

Anyone who believes this should take along hard look at themselves and their values.

@BlazingJune thanks for that, the ageism on this thread is breathtaking. I am 60. My DS is 14. He is not embarrassed by me. I am not "out of touch with the youth of the day". HTH @Pinkbonbon

@BlazingJune 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), “historically” men didn’t had to change Náppies, do the school run or breast feed, they just went hunting and left the woman take care of the house and kids.

Except the sexes of the people aren't relevant here. Either can initiate sex the first date should they wish, and the advise to either sex would be to exercise caution regarding to committing to a complete stranger.

Also - he's retired!!! That is a totally different thing to unemployed!

The people I know who were not in a regular job at this age had:

• worked in the City in really high level, high stress jobs in banking and were able to retire early (no mortgage and high savings/investments)
• a portfolio of several properties and did not need a 'regular' jobs, the income from their tenants was enough
• family money...

So there are some genuine reasons that someone would not be working at this age.

Also, I can completely understand that this man does not want a complete stranger to know his entire financial situation after just having two coffees with them...

Just ask yourself:

• do you think the age gap would be an issue?
• do you really like this person?
• do you have any gut feeling that this man is not quite right/genuine?

If you really like him I would make sure you take your time to know him better before getting any closer.

Continue dating others in the meantime. It is never a good idea to focus all your hopes and start planning for a future with someone you have only briefly met twice.

Good grief, some of the responses on here are awful. It's quite unusual for someone of his age to have retired so it's not unreasonable (if you're thinking it could head towards a long term relationship) to want to be sure you wouldn't end up financially supporting him. Of course that's a legitimate concern!

I'm not sure you can ask specific questions about money (without it coming across the wrong way) but dating is all about working out if your values align and as you casually date, I think these things just come out naturally anyway. For example, you'll find out quite naturally if he's generous or really, really careful with money and it probably won't take much to work out if his days are full and busy or if he's just lying on a sofa all day. You slowly start to build up a picture of who he is and then see if there's a way your lives can be comfortably combined.

It can be tempting to need to know everything up front but I think give yourself a set amount of time to just hang out with, get to know him and see if you're really compatible in everything from lifestyle to finances. I hope it goes well!

@BlazingJune My Dad was mistaken for my Granddad several times. Yes, I found it embarrassing.

OP, do you already have children?

You have been out for coffee twice, I think you are overthinking things. Just spend some time together and see if you get on.

The guy I know who stopped working in the conventional sense in his 40s, sold his company, did some property deals and played sport at a high level. He was married with children so obviously spent time with the family.

@PropertyManager In her other posts OP said she has assets of her own (which she feels are possibly similar to his) and he does want marriage and children as well.

She also stated he volunteered the information she mentioned in her first post.

I would not go as far as to say that some commenters have made her out to be a "gold digger," but only he knows whether he has a combination of a sufficiently substantial net worth, abundance of caution and/or negative experiences to be very much weary of marrying someone society would likely deem a gold digger -- neither OP nor people here can answer that question.

Irrespective of OP's situation, most wealthy people (all sexes & sexual orientations) who are in a relationship with a real gold digger tend to be aware of the implicitly (or even explicitly, depending on circumstances) transactional nature of their relationship -- so sometimes what is usually considered inappropriate in the early days of dating does seem to be given heavy consideration.

OP, however, has remarked this is not the case.

Previous commenters have already brought up concerns regarding age, parenting expectations and potential life philosophy differences, so I won't go into them.

Not knowing OP or her date, what I can say based on her posts is that I've observed that in certain situations people give out information and discuss issues that most would not early on, even though some might call such an approach a "red flag".

Given OP's and his age, I would assume both would be treading carefully, and consider different potential outcomes and many other factors before actually getting married and having children, if it actually comes to that.