Lovely man but his background is a bit unusual

[Lightnose]

I'm wondering if there are red flags I'm missing. He seems great, kind, reliable, funny, decent middle of the road job, generous within his means, not flash, but not shy at buying a drink iyswim. We have some shared interests and have been spending a bit of time together, not really dating exactly, but I think I might be falling for him.

Everything I know and see of him personally is lovely, we seem to share views (slightly bleeding heart lefty 🤣) on all the important issues, but can have a good debate without falling out when we don't agree, he does some charity work in the same sector to where I do my volunteering...all a bit too good to be true when you hear about his background.

His mother was a child when he was born, raised him with an alcoholic father and seems to have done a fantastic job, but he has a slightly younger brother who has never worked, in and out of prison and homeless when out. Theyre NC. He himself married very young, a woman who was married when they met and who is older than his mother. They split a while ago after a marriage of 20+ years, apparently because they want different things from life, although I'm well aware there could be another version of that story.

Anyway he seems thoroughly good and decent and all the other stuff happened to him, is not really about him, but would such a complex life raise concerns?

The stuff with his brother he can't control esp as their childhood sounds hard. Has he ever had counselling?

I'm confused, what is it that's worrying you? There doesn't sound like there's major issues there.

I think it's a mixture of a feeling it's too good to be true and knowing that complex backgrounds do affect people. He seems very emotionally aware, knows he mustn't drink much, knows what needs to be done to keep himself level, but obviously is worried about what would happen if he didn't.

Not sure what you mean by "not dating exactly."
You say you think you might be falling for him.
Wondering if you have evidence that he is falling for you?

If I wanted children with him, his background would put me off and I'd not see him again.

Just to date, with no expectations of marriage in future, I'd see how it panned out.

We're officially friends, but there's some flirting. I don't have any "evidence" but he messages me several times most days and we do something together approx 3 times a week, which IME is unusual for friends, though I accept it's being a very slow burn.

If he's emotionally aware, emotionally available, and understands and can reflect on the impact of his experiences, I can't see why it's an issue.

We're both well past the age where children are even a possibility. Or I am and he knows that and is a similar age, with adult children of his own.

How long have you known him?

This.

2 years, but we've only been spending so much time together for the last 4 months or so. We were both very newly single in the beginning and not looking to get involved with anyone.

I honestly don't think his history is complex!

The only thing within his control was a long marriage to a much older woman - that's unconventional, but not complex.

He sounds a decent guy - I consider any man decent who is generous within his means, no matter how modest the means.

Has he had extensive therapy? Because that's what I would expect, and if so I'd put his current good balance down to having done a lot of therapeutic work on himself. In which case I'd carry on taking it slowly but the story would feel coherent.
I speak as someone who has had shed loads of therapy and I freely admit I used to be a mess. And now I'm pretty much not.

@Dacadactyl How come, out of interest?

Do you have children?
Could he see you as a catch financially speaking? Some men could potentially be after that.

Send him a link to this thread and let him make a judgement?

My husband has a comparable background. Not quite the same but a lot of similarities.

My, very personal, opinion would be that you’re right to have a bit of wariness but I certainly wouldn’t write him off. It’s very hard to know how early trauma and other experiences have affected someone until you’ve known them intimately, for a long time, through difficult circumstances. You need to judge how emotionally self-aware he is.

Do you know anything about the woman he married? Sounds like he might have been looking for a substitute mum/family to get away from his own.
I know someone who married at 19 which seemed insanely young at the time but her single mum was totally chaotic and she married into a very stable middle class family (albeit to someone her own age). They've lasted the course.
Maybe this man was looking for that stability and found it and it supported him to mature happily. And his brother never had that.
Worth finding out more before leaping in, but as others have said I'd probably give it a whirl if was just me but not if there were any children involved/you want to have future children

Just because I'd be thinking he wouldn't have a clue about what I consider to be a normal family life. I'd just be thinking we would be poles apart.

I could of course, be totally wrong about that, but I wouldn't stake a hypothetical child of mine's future on it.

So he has a Mom who's younger than you'd expect, an off the rails brother he's gone non contact with, a long marriage and kids to someone who's older than you'd expect.

How does he talk about his ex wife? What kind of Dad is he? That stuff is more relevant than his Mom being 14 or his brother being an arse

This is a tricky one, and very individual.
Some people are very careful and protective of their feelings, while others are not afraid to dive in even if they might get hurt.
Clearly he comes with quite a bit of baggage, but if he has had a lot of therapy that might be OK.
What concerns me is that it isn't really clear what he wants out of the relationship.
BFF was in a group with a guy who seemed to really like her, and asked if he could call her. To me that meant only one thing, that he wanted to date her. But it turned out that he wanted a shoulder to cry on. Luckily, she was not heartbroken, but I tell the story only to illustrate that you don't always know what someone's agenda is.

They met at work, story is she was in an unhappy marriage, he shrugs and says that whilst he knows it was wrong, woukdnt donit now, he was very young.

He doesn't seem to recall his childhood as traumatic, still close to his mum (dad died when he was a teenager, missed that bit from the trauma!), but nothing a clingy way. She struggled with the marriage and that was fraught for a while, but she's been involved with her grandchildren.

He speaks respectfully of his wife and whilst starting to move on now, was sad they couldn't work things out at the time. He appears to have been a good had, still shares mutual hobbies with adult children.

See, when I write it all out, it really does feel too good to be true. Maybe it's just that that's making me uneasy? Really good single men in their 50s just don't exist, and this one is attractive and in good shape too 🤣

Yes, I am aware that I could just be filling the friendship gap that's missing now he's not with the wife who was "a best friend, not a wife".

It's nobody fault what kind of family they are born into

I do have children and am probably slightly better off than him. I'm very aware of men who need somewhere to live etc, but nothing here suggests he's after money so far. He makes sure he more than pays his way.