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If you’re not living together then I think the 50/50 seems fair to me. Likely the things you’re paying for are discretionary and offer you similar levels of “happiness/value” to both. Obviously not including any dates / spending that is intended as a gift.
Pro
Agree. Echoing BCG1 here - it depends on the context. If you really want to try a $300/pp tasting menu, then you should volunteer to pay. If he is pushing to try it, you shouldn’t be subsidizing him. Otherwise I would expect to remain around 50/50, and maybe sometimes 60/40 with you paying slightly more often but any more than that, I would feel annoyed by. Once again, if you guys are serious and are about to move in together, that’s another situation!
Chief
I’d keep it simple at 50-50, but also be cognizant of his budget when picking restaurants, activities, trips, etc.
In general keeping it 50 50 makes sense but if you want to do something that's generally more expensive than he would chose to do on his own (restaurants, plays, trips, etc.) then you should probably pay more than half to keep it in line with his budget.
we split rent on a % basis, and then kept a spreadsheet of other costs (groceries, drinks, tickets, etc.) and sent each other cash so that it was 50/50 at the end of the month. This worked for us, but if one of you is a details person and one is laissez-faire I would not recommend the spreadsheet.
We don't live together, so we don't share any of those costs. I'm thinking from a going out to restaurants/shows/etc perspective
I think 50/50 is fair if you stay within his budget (or pay for anything more expensive that you want to do).
I'm in the same boat too, I make $93k, he makes between $35-40k, he's planning to leave that for something better soon. For us, if date night was his idea, he usually pays for the whole thing and if it was my idea, I offer to pay for the whole thing, we do 50-50 too, so it depends. we are pretty frugal people so we try to do affordable and still fun stuff. we are very close so I mostly times know where he's at financially so at times like that I offer the pay for stuff, For special occasions like my birthday, he plans something nice and he's 100%, and I do the same for him too. I have planned for us a one week vacation in Orlando, Florida in August, where we plan to go to Disney, Universal, boat cruise and other fun stuff, I know it's definitely going to be expensive and its my idea because I've never been to Disney, neither has he but still I'm into that kind of stuff than him. So I plan that we split it 60-40, or even 70-30.. But also I've brought it up since January so he can have time to save up for the trip.