I had the same issue by collaring Cassidy then taking it off before the fight. The fight must not trigger if Cassidy is labeled as "friend", and collaring her again doesn't fix it. Reloading to a save before taking off her collar did the trick.
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I got you homie. Yout need to beat Cassidy office allegations when she tries to get you fired. This is how to do it. Ask Lavish, Aletta, and Audry to investigate the case. DO NOT ASK SHIORI. You can ask about the investigation by talking to them. Look for the 🔍 icon. Hire a lawyer by using your phone in your office. ( you can only do this at 8:00 AM since Aletta won't be in.) Hack Aletta's computer. You can only do this at 20:00 PM and keep going to her office to hack it every night until it's done. At some point Aletta, Audry, and Lavish will call you about the investigation. Answer the phone. At some point Cassidy will call you and ask to meet up late at night ACCEPT IT. Before the meet up buy a spy cam from the store and set it up in your office. During the meet up you can ask her questions. Ask the following.
1. Why not use daddy's money?
2. Where is the money?
3. Who's in on it?
After that go early to the office at 8:00 AM threaten the guy who's in on it by telling him to retire. Lastly show Cassidy the evidence when the boss calls you. You will be able to do this before the meeting starts. (Blackmail her) she will offer herself to you to save her ass accept it. You can coller her once she starts working for you. (Don't sleep with her she has a harem route with Sasha you can get if you dont.) Read the WIKI) Complete Aletta and Cassidy's story (martial arts and max Strength is needed ) look at the WIKI for Cassidy story. (YOU WILL NEED IT!!)You need to kill Dwayne. Lastly when Cassidy asks what you want to do with her tell her you prefer her as your slave. She will ask about her mom and Aletta. Tell her that they need you. Your done. sorry for the long post. It's long but accurate 👍😁👍