As in most non-trivial choices, context matters. I just emailed a woman that I know professionally that she is beautiful. More precisely, I replied to a photo o

As in most non-trivial choices, context matters. I just emailed a woman that I know professionally that she is beautiful. More precisely, I replied to a photo of her lying in a hospital bed with her newborn daughter "Mother and daughter are both beautiful". I had little fear she would think I was hitting on her. :) But it took a situation that extreme for me to say that. Her job requires her to be nice to me, so I surely don't want her to regret that necessity. Back in the 1980s, when ever the most impressive of women -- e.g. Ann Winblad, Sandy Kurtzig or Esther Dyson -- felt they needed a flirtatious demeanor as part of their toolkit, I usually didn't respond ... unless, of course, we were dancing at a party. ;) But I recently saw Sandy again, made it clear she's looking awesome, and hugged her a couple of times; she's over 60 now, and at this point of her life I figured she probably wouldn't mind the attention. ;)