This is actually so cool! Scratch the small itch I didn't know I had to see more of the characters from Helltaker. I have played through the first date of Pandemonica, Modeus and a secret(?) characters date, and I really enjoyed it!
And I do appreciate it's not over the top, just the normal everyday date. The small interactions, gestures, expression is also really nicely written.
The art, If you didn't say it's fan game, I might just thought this is the originals sequel.
Can't wait to see more dates added, and I do wonder how far you will go with this lol