What if you didn't have a "division of labor" with respect to finances. Perhaps then the difference in your approaches wouldn't be so wide. We have always done even the most detail and trivial financial tasks together - even after 25 years. She keeps the books on Quicken, I write the checks or do the online transactions as needed and once a month or so she gives me a backup of the Quicken file so I can load in on my computer and see how we're doing. Even now, when she plans to spend $$ on something completely unrelated to me (like clothes) we have at least talked about it briefly first (the downside is that I'm often reluctant to say - "honey, I'm going to buy some clothes" (partly because she'll take the opportunity to dress me ), so I don't buy new clothes very often). Anyway, I vote for telling him exactly what's coming and discuss exactly what you'll do with it. If he wants walking around money, hold your ground. A lot of years of not coming to a compromise about that stuff could lead to a much larger blowout later, IMO. Good Luck!
Even now, when she plans to spend $$ on something completely unrelated to me (like clothes) we have at least talked about it briefly first (the downside is that I'm often reluctant to say - "honey, I'm going to buy some clothes" (partly because she'll take the opportunity to dress me ), so I don't buy new clothes very often).
This is too funny. Last weekend we were passing thru Kohls. I said to DH, "you need new shorts for our vacation". He said "I have a drawer full". I said "many are getting old and need to be replaced". He then said "so which ones do I like?" And I proceeded to show him. He was very happy they were on sale. See how well we compliment each other!!