I was in the same situation. When I was in a long term relationship, I did a lot for my ex. I paid for everything as well as got him gifts and lent him money too. But, when we broke up, I was at peace with the situation and I was able to live with this fact.

What it ultimately boils down to is that if you’re okay with those ‘favours’ and if you’ll be able to live with it. But, if you feel that you won’t be able to do so, then by all means have a conversation with him. Try to strike a balance between doing what you want as well as respecting his wants. Good luck!

Yes, I think you should pay him back. i feel that’s when u can end things completely. you shldn’t be in debt to anyone or live on someone’s mercy be it ex or best friend. What yours is yours and what theirs is theirs. i mean come on, why should we live our life on someone else’s earnings or rather why shld u be in debt to someone who’s currently nothing to u. i personally feel if u give return the money then you’ll be
a)guilt-free
b)u don’t owe him anything and u’ll call off the relationship completely

yes i think you can do that.
that will bring you self confidence and pride.
its very rare to see such quality but make sure while doing so it doesn’t results in any type of further more conflicts