Joseph: “As far as the issue, if you were driving solo from Ashdod to Haifa and the nice neighborhood seforim store owner guy your family knew for years needed to get there too, would you offer him a ride? (Or feel comfortable if he asked you for a ride.)”
I didn’t realize that was what you meant. I have thought about that. That is why I make sure to check guys out well especially when I’ve gone out in the US. I was really upset once when a shadchan tried pressurring me to go out with someone without checking him out first and she didn’t “chap” why I thought it was dangerous (amongst other reasons).
On the other hand, the counter-argument might be: aren’t people supposed to be checking the guy out well enough to know that he is someone they would trust enough to marry or let their daughter marry?