The letters were unsolicited but not completely irrelevant. I wasn't on the inside and didn't know the inside story, but I'd had a second interview with them and the lead developer discussed their desperate status and how other candidates had accepted other offers and/or decided on different career paths after this company had made offers to them. They made me an offer, actually, and they were definitely playing lowball, which is one of their primary mistakes, in my opinion. They'd stated that they appreciated my honesty and forthrightness in the interview, and given the lead developer's lament over their inability to attract good help, and in light of the offer twenty grand under my range, I thought that I might interject. It was a risky move, but it also presented a good gauge; if the dude can't take politely-worded, pertinent, and helpful advice from the point-of-view of a potential prospect advanced in the interview process, presented in a clean, non-harassing manner, I don't really want to work there.

If the girl in your analogy spent all of the first date talking about how guys just never seem to call her from her online profile, and then we went our separate ways, had a second date where the same laments were filed, went away again, and she made a change to a profile that was stupid, then it would be risky but sensible to politely inform her of some things that she could do to improve the appearance of her profile to prospects. That's what happened here.