Could have just ended the whole exchange with a quick, "yeah, I've considered that but decided against it for reason X," rather than practically inviting him to continue with a drawn out, "okay".

Also, I can see how that would land as incredibly awkward if it was a stranger. But why wouldn't you be interested in the life stories of someone you've been dating for 3 months and clearly trust enough to be travelling with? That seems a bit peculiar to me; like maybe there's a resentment there you're not addressing and this is a mask or diversion.

Maybe. I don't know you and obviously can't psychoanalyze you or anything like that and I don't know him either.

It just seems, based on what you've written here, there's something missing in all this.