I'm VERY interested in this topic
at first I was not going to reply since I thought I had nothing to add
, but then I thought, "wait, aren't you doing some sort of dialogue system for your site mascot?" and while this is still something I'm working behind the scenes, I'll be glad to share my two cents with you.
You asked for the easiest possible route. I see your multiple pages approach and I raise you: spoiler tags (aka the <summary> tag)
(excuse the rainbow checkers, I wanted to replace it for something more readable)
You can tell from my site that I'm a BIG fan of <summary> tags. Basically, I put the question/dialogue option on the summary, and the answer on details.
I also made these little animated pixel sprites since I am using two characters, as to distinguish which is the one talking. There's also several versions with different expressions, although I would also encourage you to distinguish multiple characters' "voices" via the
font &/or
colour of their text
My vision for my site was to be able to "encounter" the option to "talk" with several characters as you browsed, placed in pages related to them, and for them to talk a bit about the page's purpose and themselves. This would take the form of its own (customized according to the character) page, so perhaps it doesn't quite match your idea to allow the user to explore the site on their own as they interact with the character.
But hey, you asked for the easiest approach, and that's something my code clumsiness CAN do!!