I noticed similar issues with other characters. It could be that intimacy and/or lewdness are too low to kick off the progression event.
I had to suffer through the same boring (no offense intended) bar brawl story of hers 10 times or so until her intimacy was maxed out to kick off the next event.
Similarly, I had to "farm" other characters' events to get either lewdness and intimacy stats up and it is hella unclear what works for how long, which can be frustrating.
The Manga Research Club quest DEFINITELY hinges on Lyriels' Lewdness, I got the last couple of points by lightly smacking her ass on morning visits and commenting it with "couldn't help myself"