We keep our finances seperate. I do our joint taxes yearly so what we make is no secret. He took on extra jobs with his friends to help pay back his debt to me (cars, investments, etc). I do this because of his history.

As much as I let it not impact my decision for who he was back then, I'm no dummy when it comes to my finances. So, if we make large purchases (a dog, cars, etc) it's with the understanding that we're doing this, equally. It usually means I pay up front and he pays me back, little by little.

I have an adult son with special needs (from a different relationship) so I'm not splurging my hard earned savings on someone who doesn't have a savings account due to poor choices in his past. Yes, it sounds harsh. It's my comfort level. I don't want to be taken advantage of.