Q. I have a deep crush on an army officer I’ve met through work. He is decisive, practical and doesn’t waste a word. I am charmed. How can I hint that I’m interested and would like to be asked out? We are due to meet in about a month’s time. I am almost 40 and haven’t dated properly for years post a brief marriage. He, I suspect, is mid-to-late forties. My 21-year-old students suggest asking him for a drink. Surely not? Any advice? He is shorter than me by the way.
— Name and address withheld
A. Virtually all nice men are shy of making passes and will do so only if certain that there is no risk of rebuff. Look for a (short) play or concert local to your meeting, ideally in a small pop-up venue. Email him to say you have promised to bring along someone presentable to a friend’s performance to lend some distinction to the audience. After your meeting could he bear to join you as you have two free tickets? Word it so that if he’s busy he can suggest accompanying you on another night.
First, he will know that you think him presentable. Second, the play or concert will give you a shared reference for discussion at the restaurant dinner to which he will insist on treating you afterwards.
The important thing is to signal your interest. So many attractive men blunder about singly for years because they assume no one wants them. They are there for the taking once emboldened by the self-confidence your stated approval will bestow. Obviously, don’t overdo it.
Q. I am a single man of 28 and my social life is so hectic that although I really enjoy all the dinners and weekends, I seem unable to make time to write and thank people. The guilt is hanging over me like a pall but I can’t get organised on this matter.
— F.B., London W11
A. Carry a wad of postcards in your sponge bag. Write one before leaving the premises and leave it propped somewhere to pleasantly surprise your host the next day. Even if it is only a few words for a dinner, though obviously longer for a stay, the charm of finding the unexpected missive will compensate for the non-receipt of the snail-mailed expression which is so increasingly hard to achieve.
Q. I have bought a rather small but very expensive box of chocolates as a gift for a family member. I know they will enjoy them but be rather oblivious to their full cost. Is it ever appropriate to have ‘forgotten’ to remove the price tag? Or is there a better way to convey the value?
— G.W., London, SW11
A. Look portentous as you hand over the chocolates. Say: ‘These are just for you so hide them away. They are so good they’re not so much chocolate as medicine. Google them and you will see how special they are.’