I think this encounter can be an important lesson to stay cautious.
JGeropoulas said:
I can’t see any incentive for him to weave such a tale for me, a complete stranger. I did think his behavior exhibited poor boundaries and was rather inappropriate in that he was so disclosing to someone he’d just met. But once I heard what he had to say, I could see how he might open up so much once he realized I “had ears to hear” about such things.
In that instance, you could've nodded and then when the conversation was over, say you have an important appointment and then leave, if possible. Your story reminds me a bit of an experience I had last year. An old man (who seemed genuine and kind) started talking to me about his abduction experiences (after having met him for 5 mins), and how he was working on very important alien technology 'with help from above' and which he hopes to finish soon. He gave me all kinds of details on how the secret agencies were going after him. And he claimed, the 'people from above' will be here to help us. I just nodded and said that's interesting. All he did was talk and didn't leave space for much of a response, which was good, because I think in such cases, it's probably wise and externally considerate to let them talk, while you look for a way or an excuse to excuse yourself (rather than engaging in it and encouraging their beliefs), especially when you get suspicious!
JGeropoulas said:
Then I reciprocated his hospitality by offering to drop him off (6 blocks away) on my way out of town. If that's naive and careless, then I'll have to rethink some things, I guess.
Perhaps a simple thank you would've been enough for his hospitality, or maybe offering to pay for his drink? I wouldn't give strangers a ride (unless you're absolutely certain they're ok), especially considering his stories.
My 2 cents. :)