They were at the same schools, but MC doesn't remember her. Maybe just middle school? The guy working at the theatre has had a crush on her since those days, and Todd is aware of it.
And if we're looking at the beginning of the story, the whole scene with the nurse is sus. Like, she doesn't page a doctor, mask up the whole time (not inherently sus, but is a bit in the context), knows Jenn's name.
And why exactly were those three women going to the law offices? Is it relevant? Seems probable, but there could be a simple explanation.
One thing that's tricky is, it is really hard to tell if the dev is taking the mystery elements seriously, or if they are just mystery boxing the setup to handwave the planned sexy times. I could believe arguments for both sides, at this point.
ie. is reality going to rear its head at some point and there will be a reckoning? Or is it all just spice and an excuse for everyone to be horny?