The other day, a 60-something female, widowed client of mine received a message on Match.com from an accomplished, seemingly nice man. In her first response back to him, she asked – point blank – “Why have you never been married?”

He replied very politely, saying that it was a combination of things, some work-related and some more personal. But do I think he owed her a response to her extremely terse, invasive and premature question? No, I don’t.

I quickly wrote this message to my client:

Since you’re sharing this exchange with me, I want to provide some feedback. I know it’s tempting to ask why someone hasn’t been married before, but first, his prior marital status does not define him as a person, and second, there are often so many variables that can’t be distilled into one message, e

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