Same here. I have given her the first massage after the last training event, but the next day it isn't possible. Once you start the training you can't even leave the area until you give her the massage, which isn't possible.
As far as I can tell, I am currently softlocked.
I have:
-Progressed with Jirou to the point she talks with Tsu in the park
-Progressed with Tsu until finishing the cave with the thighjob scene
-Had the 2 dates with Midnight
-Gave Mei the high tech thing and guitar string
-Beaten the robots from kiri
-Trained with ochako until (assumed) softlock