Dear Prudence,
I have been dating this woman for nine months, and it has gotten very serious (at least in my mind, and I think hers too). We are both in our late 50s and she is retired and I am still working for myself. We haven’t talked about money, but I know she owns two homes and has a very expensive car and takes expensive trips. So, she seems well-off, which is great. I am truly happy for her. I am still working and do not have quite enough saved to retire but hope to get there in the next couple years.
The issue is that for the length of the relationship, I have paid for everything. Every dinner, lunch, breakfast, and hotels, etc. I am fine doing that. I think I am a generous person and I understand while we are dating, I am courting her and I am not the kind of guy that would ever ask her to split. But I am wondering if this is the way it will always be. And moreover, do I need to think of working longer to have enough money to pay for everything forever? I am truly crazy about this woman and would do anything for her. I am just wondering if I should bring this up, and when, and how.
—Not Sure