Mary Killen Mary Killen

Dear Mary | 17 March 2016

Plus: the charming way to avoid sending thank-you letters, and the discreet way to reveal how expensive your gift was

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.

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