Characters write to an advice columnist
Interchange #1:
Dear Miss Manners: As a man of professional responsibilities requiring tact and finesse, I have nevertheless kept myself apart from the fray of entanglements of a personal nature, being disinclined to the experience and expression of human emotions unless as germane to political dealings on a worldwide stage. However, now in middle age, I find myself unexpectedly drawn to a man whom I encounter via a family connection which has led to contact in matters of business. He is intelligent, kind, gregarious, and I have no idea whether his ... tendencies shall we say, would make him at all amenable to an overture of a more social nature. I place great stock in the value of the rules of engagement--what you might call etiquette--in guiding such matters. I trust you can advise me appropriately.
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Gentle Reader: I hope I am nothing if not appropriate. Fortunately, as challenging as it might seem due to your stated lack of experience, your dilemma is not a difficult one. Simply ask the gentleman of your acquaintance to dinner, or, if that seems too big a step, to lunch. Do not muddy the waters by implying that your invitation is related either to the familial connection, nor to any potential business matter.
The "rules of engagement" are, in fact, quite the same as you might have encountered in the more agreeable aspects of your professional life. The goal is to make an offer and either pursue with propriety or retreat--perhaps temporarily--with dignity.
It is to be hoped that his "tendencies" will reveal themselves if he is made to feel appreciated as a charming dinner--or lunch--companion and allowed to "be himself." Best of luck to you.
Interchange #2:
Dear Dan: So, this is a bit awkward, but given my situation, I thought you'd be the best one out there to advise me. I'm a forty-something, lifetime heterosexual man with vague bisexual leanings, which have of late become more un-vague, if you know what I mean. I've recently developed an attraction for a man who, let's face it, is out of my league in terms of class and bearing. But at my time in life and in my line of work I know better than to waste time. So I've decided to take a risk and make my move.
But I have no idea how. I was married for years, played around a bit before that, and hardly at all since, and anyway have no experience with men, either reading their signals, communicating interest, let alone anything else that might follow. Can you help an old copper get going again?
Naive Silver Fox Wondering
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Dear NSFW:
Congratulations and kudos for taking this risk. Now here's the good news: there's nothing different about reading signals, communicating interest, or anything that follows between two men, two women, a woman and a man, or multiples of the above. Well, wait. There is some different with what follows. But the first two? Let's face it. It ain't easy no matter what the combination. In fact I know some people who find it easier with the someone of the same gender, what with chromosomes and socialization and all that.
So, go at it as you might with anyone. Ask him out on a date, for a meal or to a show. You communicate your interest, and trust him to convey his own signals. As to what follows, do a little research (keeping in mind that porn isn't always realistic blah blah). Or, if he is more experienced, let him take the lead.
If he is not--despite the class and bearing, screw that out of your mind, he's not out of your league--then the two of you can go on a great voyage of discovery, together. Bon voyage.