to have spent so much money
No deberías haber gastado tanto dinero en eso.
You shouldn't have spent so much money on that.
Tom deseó no haber gastado tanto dinero.
Tom wished he hadn't spent so much money.
No debiste haber gastado tanto dinero en tu pasatiempo.
You shouldn't have spent so much money on your hobby.
No debí haber gastado tanto dinero.
I shouldn't have spent so much money.
No debieron haber gastado tanto dinero en su pasatiempo.
They shouldn't have spent so much money on their hobby.