Dear Mary: How do I avoid getting short-changed when my coupled-up friends split the bill?

Q. A very good friend, who has been incredibly generous in the past, is feeling the financial squeeze, particularly with the inflation we are all suffering. I would like somehow to contribute regularly to his monthly expenses but can’t think of a way to do this without offending him or getting a refusal from him. His passion is hunting and I was wondering if I could set up an association for impoverished sportsmen. Do you have any ideas, Mary?

 – Name and address withheld

A. It would be simpler to inform your friend, in a businesslike manner, that your will is in preparation and it includes legacies for a handful of friends, like himself, who have been exceptionally generous to you.  You have been told it would be much more tax efficient to pay the recipients while you are still alive, so would he kindly supply his own bank sort code and account number?

Q. I am 28 and often go out with friends to restaurants. Since most of my friends are fairly old-school, the bill is always divided between the men. The problem is that my girlfriend has dumped me. Now if, for example, we are seven at the table, the other three men with their girlfriends, I will still pay a quarter, rather than a seventh, of the bill. What could I do to avoid this situation without looking like a cheapskate?

– Name and address withheld

A. If you are moving in these old-school circles it would be better to rise above the inequity. But you could turn the situation to your advantage and accrue goodwill by inviting a platonic guest to the table. You will pay a quarter of that bill on top but will enjoy the sense of ‘fairness’ as the other men subsidise the rest.