Here is, word for word, an email I sent to KJ asking her advice this morning after an incident on the way to work. Any thoughts are appreciated.

(I should note that, on re-reading, I think I failed to communicate the amount of moxie the young woman showed in her responses to him. She had a do-not-give-me-shit shield that she put up from the first moments of their interaction.)

So, this morning I was standing at the bus stop with a very pretty
young blonde woman when a much older guy wearing nice but strikingly
mismatched clothes dashed through traffic to join us. As he ran up he
said to her, “How much is the bus,” indicating that he’s new around
here. He then looked abruptly at me like I had said something, then
turned back to her for her answer. She told him that all the buses
are free and he immediately started “joking” about “Hey, why don’t we
run away together, then, let’s just get on the next bus and see where
it takes us,” etc. She laughed it off with obvious nervousness and
then he got on the bus with us – I got between them when we got on, but
the bus was empty (spring break) and so he had plenty of ways to sit
near her – and started pointing out cop cars in sight. “Are they
looking for *you*?” she asked him, which got a chuckle out of me. He
said no, the only reason they would be looking for him is if he
*didn’t* talk to her because that would be a crime, hardy har.

There were a lot of things about him that sent up red flags: a
generally manic air, the fact that he was wearing two watches and
carrying a third, that he was carrying a pair of glasses he never
seemed to need (a classic of social engineering, as someone carrying
glasses is strongly associated in most minds with professionalism,
doctors, lawyers, scientists, people assumed to have their shit
together). She pointedly asked about the watches and he said “Well,
you know, the recession.” He then launched into a sob story about his
sister and how she died of brain cancer and lung cancer and he had to
decide to pull the plug, and way, WAY before she needed to, she pulled
the cord to ask the driver to stop at the next bus stop so that she
could get off the bus.

Her body language told me – and him – that she wanted to get OUT OF
THERE, to the point that he said, “So, if I got off at the next stop,
with you, and walked with you, would that bother you?” She didn’t
hesitate to say that yes, that would bother her, and she’d appreciate
it if he did not do that. He tried another limp round of boohooing to
try to sway her but she ignored it and when the bus (finally!) stopped
she got off in a hurry with a backwards, “Thanks for an interesting
morning.” He said something inexplicable (“Thanks for an interesting
life,” I think) and then looked at me and I looked back at him the
rest of the way to *my* stop. He got twitchy in a big way and kept
producing this dry sniffle that I’ve always associated with major coke
heads and that would explain a lot of his mania and talkativeness and
generally sketchy vibe. My goal throughout – as I was paying obvious
attention to him throughout his monologues to her – was to make it
clear to him that there was someone else around who was noticing him.
I wanted him to be sure that he couldn’t do anything without someone
having a good look at him first.

My quandary is, should I have asked her if she wanted/needed help
getting rid of the guy? I consciously chose, when she from the get-go
seemed to be onto his antics, to take the stance we’re trained to use
at elections: when someone wants help, they will ask for it. Should
I have intervened, though? More than once I opened my mouth to say to
the guy, look, lay the fuck off, OK? I didn’t want to step in where I
might not be wanted, though, and I didn’t want to suggest that she was
somehow incapable of ditching him and, happily, it turned out that she
was (capable). I honestly don’t know, though, if I drew the correct line on
when to intervene in what seemed like it had the potential to get
weird in a bad way.