I persuaded a shy male friend to try internet dating. He posted his profile and photo but never actually wrote to anyone. So I got him to let me take over. Now I am courting three women via e-mail, in the guise of a 35-year-old man. I am a woman (but, it turns out, I have a way with the ladies). This now feels a bit less innocent, but if it gets my shy friend together with a nice woman, is it wrong?
Anonymous, New York

Randy Cohen: This isn’t an ethics question; it’s the premise for a romantic comedy. In the hipster art-house version, you discover erotic possibilities you’d never considered before. In the square airplane version, the most alluring of your e-mail correspondents turns out to be — surprise — a man writing as a woman to help a friend, and you two fall truly and deeply. In the modern-violence version, your shy friend feels humiliated by the whole episode and goes on a killing spree, with you as his final victim.

OK, it is an ethics question, and one that illustrates the perils of over-reaching. You did well to help your friend look for love but erred when you engaged in impersonation. Now it is your turn of phrase his intended inamoratas are drawn to, your flirtatiousness and allure. You’ll succeed only in bewitching a woman who expects your friend to be someone else, a dubious basis for romance. That’s why I don’t have the ghost of Shakespeare to make my courting calls for me (that, and the obvious technical problems).

Such misrepresentation — displaying one item when another is actually on offer — is associated more with disreputable electronics dealers than honest wooers. When the truth comes out, the women you deceived will feel hurt and embarrassed, a good guide to the impropriety of your deception.

If this were a chat room where roles are more fluid, your actions wouldn’t be deceptive, just playful. But the expectations, or at least the hope, in online dating is honesty.

As you know, literature offers a cautionary tale about such tactics: Things didn’t work out well for Cyrano or Roxanne or Christian. And so, as a matter of efficacy as well as ethics, you must abandon your imposture. At a minimum, your friend must immediately replace you at the keyboard. Ideally, he’ll ’fess up to everyone and hope, the malfeasance being well intentioned and evanescent, that his dates are more charmed than wounded by this brief and tender treachery.

Philip Howard: Yes. You are playing with fire, deceiving the gullible, and risk landing some poor sap or sappess in the minestrone. Probably your shy male friend.

Internet dating is by its nature a second-rate activity. It bears the same relation to flesh-and-blood dating that the reflections in Plato's cave have to the real world outside. The fact that you are ashamed to sign your name to this e-mail suggests that you are aware that what you are doing is shifty. Or, to avoid euphemism, dishonourable and dishonest.

I am aware that blogging on the internet is a second-hand activity and a sort of game. It is not to be confused with more serious contacts by person, voice or writing. And dating can also start as a kind of game. But relationships are also the most serious activity that humans can engage in. If the activity remains just an exchange on flirtatious keyboards, it is a kind of infotech masturbation. But if it actually leads to a meeting of man and woman, it matters.

You may think that you have a way with the kind of ladies who go in for this kind of childish perversion. But you are doing your shy male friend no favours at all. I should think you run the risk of confirming him in his shyness, if not turning him into a misogynist and a Stylites, or pillar monk, in order to escape from interfering females.

Leave him alone,you silly woman. Get a life. Get a man. Even, if all else fails, get a guinea pig. But match-making in drag is not a joke. I know that such deceit is a running theme in Shakespeare (Malvolio, Beatrice and Benedict). But that is Shakespeare, and a play. I reckon that you are skating on thin and grubby ice.

A prop maker at a theatre, I was told to attach some books to a set piece with screws. Many of the books were old copies of the Illinois civil code and such, but one was an early edition of Sir Walter Scott’s poetry. I could no more drive screws through it than shoot my best friend. So I simply took it.