This has been reported by so many players that I think is a bug.
I would like to help you more asking you to share a save at the point you are locked, but unfortunately v0.98 and v0.98.5 don't work anymore on my machine after latest bunch of Windows updates, and fucking KB5028166 can't be uninstalled, damned Microsoft!
I can suggest you to take a look at the second part of
this post of mine, where I discuss the same bug with another player.
At that time I haven't yet guessed it was a bug and I said to the player that he might being confusing two gameplays... but since then a lot of players reported the same problem, so it must be a bug...
Anyways, the workaround I suggested in that post might work for you as well.
The only drawback is that after manually changing that variable you have to redo the "I have two bottles of wine" threesome scene, but it should give you the possibility to ask Ruby for a date if you go to the sport center the first day she works there immediately after the threesome.
IMPORTANT: during the threesome you have to hold Valery to let Ruby finger her, or the dialogue for asking Ruby for a date won't be available at the sport center.
Let me known if it helped or not.