Dear Mary: how can I matchmake two dinner guests?

Q. What is the best seating plan when you have a supper party where you are hoping to matchmake two of the single guests? If you put them next to each other, everyone will stare to see how they are getting on. Or is it better, when you move everyone next door, to have coffee and then say ‘Who hasn’t talked to who?’, and put them together then?

-— A.E., Pewsey

A. It is risky to wait till after supper. Smug marrieds may want to head to bed all too soon and if the crowd thins too much, the singletons may not have enough time to bond before they feel pressured to leave as well. However, just as in speed-dating, physical proximity, rather than conversation, will be the key determinant of whether or not they fancy each other. Therefore put them side-by-side at the table despite the surveillance. In the days after the party, don’t wait for the singletons to contact you to thank you. Find a pretext to ring them and casually probe for feedback. Share anything positive to embolden a follow-up exposure.

Q. I have recently been diagnosed with a serious illness. Family and friends have been very supportive and have sent a range of delightful gifts. However, one of the gifts was delivered without information on the sender who, despite discreet enquiries, remains a mystery. I do not want to write to everyone in my circle as it could embarrass those who have not felt the need to send a gift — which is fine by me. Mary, can you suggest any strategies that I could use to find out the identity of the sender?

— J.L., Edinburgh

A. Send a bcc email to everyone in your circle saying: ‘Your recent great kindness has been much appreciated.’ Leave it up to each individual to interpret whether you are simply referring to their emotional support, or to the present that they have sent.

Q. Someone I was close to at Oxford had a relationship with a woman we all felt rather alarmed by. In fact, we referred to her as ‘the stalker’. My friend moved on and eventually married someone else, but his marriage broke down under Covid. Right on cue, the stalker has come out of the woodwork asking for the email address of her old boyfriend. Awkwardly, the request came via a senior colleague of mine who is apparently a close friend of the stalker. I am loath to put her back in touch with someone whose morale is so low that he may be tempted to reheat what could be a rather dangerous old soufflé. — Name and address withheld

A. It’s not up to you to block the stalker’s access by playing God. There is no need to reveal the email address of her vulnerable former boyfriend. Just forward the request and tell your colleague you have done so. If he fails to follow up, you cannot be blamed.