Head or Heart in love/finance

[Rainydayss]

Been seeing a lovely man for several months now, very kind, loving and thoughtful. However financially he struggles, lives alone and decent job but paying off some debt and no financial security, savings, pensions etc. No bad habits of gambling etc, but just feels the strain making sure all the bills and debt are paid each month.
A could of people suggested I could do better, purely based on materialistic reasons and part of me thinks maybe they are right (and I hate myself thinking that). I'm independent financially but worry about the long term financial situation.

Has anyone had a similar situation? I'm reluctant to get any more serious with him based on what people think, which is ridiculous I know

Money doesn't make you happy. He sounds lovely and finances are much easier when shared - something for you to ponder there.

Do you know what the debt is from? Sometimes people end up with debt due to circumstance - series of unlucky events they had to pay for and debt was the most accessible way. But sometimes it's due to issues like addiction or just general overspending/financial illiteracy/living above their means. Either might point to potential future difficulties in a relationship, especially if his financial habits end up crossing from debtors to your money.

I think you're right to be cautious about potentially merging finances, if that is what being more serious would mean. I wouldn't say you need to go chasing after someone who has loads of money. But if you're financially secure, then getting together with somebody who is not is a risk. I'd want to know why first.

Yes definitely if we were to live together things would be much easier and we could have more treats/days out. It really gets him down and he feels he isn't good enough that he isn't in a better place financially (in 40s). However I know this is just circumstances and many of us at that age struggle especially after divorce/splits etc

He helped his ex girlfriend pay off the arrears on her house and got a loan to help her so paying that off now they split, he's been too soft in past relationships and walked away with nothing.

As long as it wasn’t the result or gambling/impulsive spending, and he was financially sensible with what he did have, I don’t think it’s a big deal at all.

When did he split with his ex girlfriend? Why is he left paying off her debts? Sounds really fishy to me.

Do you own your home? I'd worry he was hoping to move in to your house and live rent free.

My advice is be careful. Protect yourself and your money. Don't let anyone with a sad story take advantage of you.

So even if the debt is from being a big softy to ex, what's the reason for no pension etc? He can't blame his soft heart and his ex for that! How many of these exs is he blaming for 'taking advantage' of him? All of them? If he walked away with nothing each time, I'd presume he started the relationships with nothing too!

Presumably he was living in her house when he took out loans. Where did he live before that? Or has he always moved in with women?

If he's have issues and paying off debts, surely getting a second pt job would be better than being 'sad'?

Why are you thinking about how life would be easier if you lived together after dating for a couple of months? I presume it means him moving in with you? Have there be hints from him? Even subtle ones?