ARE HIS MANNERS TOO OLD-FASHIONED?

QI am in my mid-50s and have been divorced for five years. We were never able to have children, which I have come to terms with although it drove a wedge between us. I threw myself into my career instead and have done extremely well. I have now started dating again and a couple of months ago, I met a very nice man. However, because he is of a certain generation, so far he insists on paying for everything when we go out. I have explained that money is not a problem for me and that I would like to go halves but he looks hurt. He seems to almost take it as an affront to his masculinity. To be honest, I find it a bit sexist and I am wondering if he is too old-fashioned. In every other way, though, he is lovely.

AYes, his attitude to money could indicate that he is a little stuffy or old-fashioned, and if this was reflected in the rest of his personality, it would be a warning sign. But as he is so nice in other ways, I wonder what more is behind this. Maybe he has not been as successful as he wanted in his own career, or spent a childhood or a previous marriage living up to impossible expectations and believing he is somehow not quite good enough. So he could feel as though he needs to impress you and that if he doesn’t appear successful, then you might get bored of him. You won’t know unless you really talk to him about this. If I were you, I would be direct and straightforward. Tell him calmly and politely that it makes you feel uncomfortable when he refuses to let you pay and that in order for your relationship to flourish, this issue really needs to be resolved.