For the first time playing Skyrim, I decided to play along the timeline once in Riverwood. When Gerda asks me to deliver word to Whiterun, I left for Whiterun that very evening. I did not do anything else in Riverwood first, except sell all the Helgen junk.

When I got the quest from Farengar to get the Dragonstone, I went back to Riverwood to do things there. I wanted to spend the night in The Sleeping Giant in Riverwood and talked with Ognar. A conversation selection was available that I had never noticed before, "Where is the Innkeeper?" He simply replies that she is gone. So I could not rent a room.

After clearing out Bleakfalls Barrow and returning the Golden Claw, I head back to Whiterun to deliver the stone and when I get to Farengar, who do I discover is there in a meeting with him? Delphine! It is such a cool explanation about a few things and I have never witnessed this before!

I have well over 700 hours playing Skyrim with many, many characters and this is a first for me

Sorry if I got a bit excited there, but it is so cool to come across new things in a game one has put so many hours into

I've read this somewhere.....

Yeah it's amazing how excited people get over the little things.

Yeah, Delphine hired whats his nuts, the annoying condescending mage in Whiterun, via proxy due to her being in hiding technically.

I always find a new thing in Skyrim that I never noticed before.

Never thought of doing that. That's interesting actually.

Hiding. Sure. That's what she tells herself whenever a Nord smacks her on the bum whenever she serves drinks.
"...I'm in hiding, don't blow your cover..."
In reality, she's just a barmaid now of fallen glory.