I’d just like to add OP I don’t know if you’ll come back to this thread but my final piece of advice is try and get better at doing what I call horizon scanning. Based on a man’s history, plans and current situation what may likely arise in the future?
For instance I was talking to a guy who was 45, no kids thankfully but he was studying at uni for a BA in marketing full time, while working in a bar part-time and living in London. I asked him what his plan was after his degree and he said he wanted to be a “life coach”. To me this guy was a massive gamble likely to end in a loss to me.
It was all so predictable, I could just see his mental plans - a woman would subsidise him through his student days ( it’s not cheap as a student in London after all) ! Then he’d graduate and start faffing about trying to generate work as a “life coach” or getting a masters instead of full-time work.
It can work, some people make money as life coaches but it’s not a sure fire plan like a man who is looking to get a job as an engineer or banker or even a teacher and it can take a long while to generate a strong client base. And there was no real reason why he couldn’t start building his business during uni since you don’t need a degree to be a life coach, but for some reason his plan was to delay it until graduation despite the fact he was going to be 49 by the time he graduated.
So realistically eventually the woman would have to bail him out while his business gets on his feet. So you’d be signing up to support him for the next 7- 10+ years. That is far too much for a new relationship. Especially if you’re not 21 anymore. And no doubt he’d probably leave them for a younger woman once he got established in his 50s . And he did actually disclose he usually dated women 15-20 years younger!
He also had an unimpressive track record since he couldn’t seem to account for what he had been doing career wise other than “working in ice cream shops” before he started uni and he had no assets at 45.
Get some self respect, ditch this man and if you ever meet someone who is going to have to depend on you for several years again please run - it’s likely they see you as a source of support rather than someone they genuinely like and they will eventually leave for that person they really want to be with.