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Hello, this was a recurring bug we had... I tought it was already fixed... that's why we added a function that allows the player to skip applying the oil, does the option appearts to you before starting the minigame?

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The only two options prior to the minigame are 'Just Chatting' and 'Want me to put some oil on?'

Mmm weird... where are you playing? Mobile? PC? Mac?

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PC; its also entirely possible the save is causing the issue as it was a save I have carried forward for a few updates.

I was noticing the message minigame was broken before I had the "Convince" Latisha quest. 

Try downloading this save file and put it in your game, it should place the game right before asking Jessie for the tickets.
https://thehighschooldays.com/downloads/1-1-LT1.save

To locate the safe files, check this page: https://savelocation.net/renpy

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Okay that seems to have worked using the save provided.

There does still seem to be an issue with MC stamina not resetting when save scumming, I have to rollback the frame multiple times to refil MC stamina bar. Still no skip option. 

Then I was having an issue with Latisha's pleasure bar not increasing barely at all resulting in it never reaching the first third of the bar. I redid the mini game on Sophie and her pleasure bar was working correctly, went back to Latisha and then it seems to have fixed her pleasure bar as it was acting like Sophie's so I could progress. 

I appreciate the assistance!

For Latisha, you need to be wearing the bermuda swimsuit, the speedo wont work with her. Also, you could use the "Apply oil" option, that will give you a boost for 5 clics but you can use it as many times as you want.