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I really admire RMS, and while I don't exactly understand why he'd put a flirtatious email chain online, I hope he finds (or has found) personal happiness.

FWIW, there's no reference to his dating life in https://stallman.org/rms-lifestyle.html

I really cannot fathom why someone would post this on their website. Stallman is unquestionably a genius, but there's no denying he's an odd duck.
And then there are those whose ex-girlfriends list might require an additional hard drive.
He started out strong with that witty application to the ex-boyfriend list. However, once the Lady said she was with a surgeon, that was probably the clue that it was time to bow out. Really enjoyed this, but felt a bit of sympathy for Richard.