Comments for the first letter:

Anne, you’re absolutely correct. It is perfectly acceptable (though not necessarily wise) for a man to introduce himself to an attractive woman (or any permutation where strangers encounter each other with a romantic interest). The question is whether or not the two people can demonstrate good manners long enough to actually get to know each other and see if they’re a good fit. For example, if a man who is recently divorced is interested in finding companionship, what should he do? Should he sift through all of the acquaintances of his married friends, some of whom won’t be allowed to speak to him because those friends of his are also married to his ex-wife’s friends? Perhaps he can start waves at work by engaging in a personal relationship at the office.

Jay’s letter is a little different, and I’ll be a little more brief about it. In this case, his date should have said something about this being a work-related event. Maybe she didn’t because on the third date, she was a little nervous about “throwing him to the wolves,” and didn’t want to give him a chance to say no. All he needs to do is explain that he’d be willing to do it again (if he is), but maybe she should tell him about it first, so he can get some pointers, be on his “A” game, etc. It demonstrates support for the event and discreetly requests the kind of respect anyone deserves.

Most of the time here in NY (Manhattan) it is a “sale”…!