If you can, join the discord via the link at the top of the page and post your issue in the bugs channel. They might be able to fix your save
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Do you need to increase each bar to 3 or 4? For 3, do the best you can (you won't max it) then spy on her room. You'll see her friends use lotion on her bottom (if I'm remembering correctly). You can then buy this and use it in punishments. This will be the key to levelling Rachel (and Cassandra) up.
If you've done that, then make sure you've maxed Debbie too. This should give you the options you need to level up further.
Jimmy's quest is to do with the keys. If the girls can play volleyball and you've taken the big towel then that part's complete.
Go to the sports centre on Thursday afternoon (I think) and speak to her when she takes the girls for a run. Then, head to the changing room and take a shower while she's out. She'll return while the headmaster is still in the shower. You should get the scene then :)