Okay, so 100% the people you'd ask depending on who your route was going down had to be scripted to be able to do this. Otherwise you could accidentally soft-lock yourself and cause a game over (or reset). Though, who would you go with if your route was with Virgil seeming how he was already evolved? No, I guess since this is supposed to be a 2nd year event, it could still be Virgil? But he's already evolved...
After rechecking CH 41, I'm even more confused. "And third, you need a very high affinity with a specific love-interest character! So basically, it's a event meant to be cleared together with a specific character once your route with them is locked in."
It has Virgil there in the background blacked out.
So this is something that can only be cleared with Virgil? But even then, since you, the protagonist, can have any element- wouldn't it change? Virgil will always have the wind attribute, Anna can have any attribute. Grace was fire and water, though I'm sure in the original game she probably had Water- Since it couldn't be boosted by Virgil to the same degree fire could be. Or maybe it was simply a different magical geometry setup, and I'm simply overthinking.
All I know is I'd get to this part and start looking up a guide on how best to skip through this tower asap.