Splitting expenses: 2nd marriage, later in life

Honestly this is beyond the scope of a wedding forum, but I would advise that before getting married to see a lawyer to talk about financial expectations and a possible pre-nup. Good luck getting it sorted and congrats!

One of the main things that makes or breaks a marriage is that people are not on the same page where money is concerned. You need to figure out between you how to do that. Sometimes that means bringing in a professional.

Are you both working? I would start by putting an amount that is proportional to each of your incomes into a shared household expense account. If one of you earns less, it's not fair to split everything 50:50 IMO. You can get into the weeds and account for the difference in the food bills before and after, but that seems a bit petty to me and where I live that food budget doesn't sound all that unreasonable, certainly not if you are trying to eat healthy, or organic. There may be other expenses where you are getting greater use or advantage of whatever it is.

If you are committed to keeping things separate I'd look into a post-up that will protect the home and what you each brought into the marriage. As for the money he's saving by not having to pay rent, you are on even footing there, plus you have the value of the home. Personally, I'd look forward, not back on that issue.

I would have a conversation about the expenses. Rather than “you take this bill, I’ll take that bill”, I would split the cost of things down the middle that you utilize equally (things like utilities, water, trash/sewage, internet, etc.), but come up with a different solution for items that are not being utilized equally (in your case, the grocery bill). I would let him know that you are only comfortable spending $X amount each month on groceries, and the two of you could figure out how to get the grocery bill down to that amount. If he insists on continuing to go way over that budget, you could either split the bill by consumption, or you could each just be responsible for purchasing your own groceries.

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I agree with this. The two of you should determine an actual budget to follow to split 50/50 and anything beyond that he wants to spend he can take on his own. He's living for free because you've spent years paying off your mortgage, it isn't just free housing.

Consider a post-nup and have meetings with a professional regarding future living expenses, estate planning, and inheritance. One topic to discuss is vacation. Is your spouse willing to cover all vacation costs if utilities and groceries are split equally? I expect he likes five-star accomodations. I'll be matter-of-fact, there are certainly examples of people marrying for housing in middle and elder age. I hope you two can work on financial transparency and a plan.