I'm actually trying to figure that out myself right now. As well as the Aunt "She is ready to take the next steps herself we must only wait" and Nurse Pearl "I guess we need just train with her."
The reference to training with Nurse Ali made sense since you find her in the gym, but Nurse Pearl is only either at work or her house (which I can't find). There's also a reference to training Ash in her earlier notes, but a couple of times visiting and doing something with her eventually turns into a scene. Not so with Nurse Pearl.
*edit* Nevermind, I figured out Nurse Pearl lol. Didn't realize that once you got far enough in Nurse Ali's story that it was connected to Nurse Pearl.
*2nd edit* So I didn't see what the trigger was, but eventually the mom just showed up in my bedroom when I went to go to sleep. Still haven't found a trigger for the Aunt, and I got Nurse Ali to a full 5 affection but can't for the life of me figure out how to finish Nurse Pearl to 5 affection. She's stuck at 4, and the hint is to win the sparring (presumably with Nurse Ali), but I can't find a trigger anywhere to finish Nurse Pearl. Spent days with Nurse Ali looking for that "Seduce Pearl" option that there had been previously, and days with Nurse Pearl in case the trigger was in her dialogue somewhere to no avail. Has anyone finished Pearl or the Aunt?
~Morningfrost