A man would never ask us this!
STEPH SAYS:
What strikes me here is that this letter would never have been written by a man. It’s considered normal for the man to pay for everything, but when those roles are reversed it’s suddenly shocking.
So, the first thing I think you should do is consider if you
really mind or if you just think you should mind. Because if it’s the latter, and if he’s making you happy, then it’s your choice if you want to keep paying for his taxis. It’s your money after all!
What does concern me, however, is that, at 60 years old, he is basically still sleeping on people’s sofas — albeit in a slightly more grand fashion.
you say he is friends with people of means and this doesn’t surprise me. I bet he is ruthlessly charming with knockout charisma, and, as you describe him as a ‘silver fox’, he’s clearly not short of sex appeal.
Some well- connected chaps spend their entire lives in a kind of suspended animation — they never move on from school. they have the same circle of friends and, as they’re the Good time Charlie of the group, they’re always invited everywhere. and let’s face it, if you’re always invited you’re basically not paying.
the problem here is not that that’s how he chooses to live his life, it’s that you are feeling short-changed by it. Maybe you thought he was as wealthy as his friends (who I daresay know he hasn’t a bean and couldn’t care less) and are now feeling duped? Or maybe you’re just disappointed he’s broke.
Of course, it could be more serious. there are shades of oldschool gigolo here and if he asks you for a penny more than the supper bill, you should run a mile. you don’t say how you met and it is possible he has singled you out as being comfortably off and is, indeed, intending to take advantage of you.
But, if it’s limited to tickets to exhibitions and a coffee or two, or a few cocktails while you have a ball together, then there isn’t any harm in it. If that’s the case, then he is probably treating you in the same way he does all his friends. and there are benefits that come with spending time with a charmer — a massive amount of fun for starters.
My advice is that you tell him you’re feeling the pinch financially, that you can’t keep funding everything. then it’s up to you how much you spend on your nights out — treat him as an occasional treat.
Consider paying for him as part of the cost of your night out — and if you think he’s worth it, then why not? Just make sure you don’t blow the lot.