Not RNG, just a set of requirements that - in retrospect - feel a bit arbitrary and sometimes might leave you in the dark.
Arc can’t exactly afford to keep going back and polishing stuff, new content takes priority and all that jazz…
Concerning Jessica. I’ll assume you are on Act 1. You need to have gone to the college once so the event with Jessica triggers.
If you don’t have the college, you have to check Emma’s room - I think at night - so it advances.
Like I said, not RNG, just convoluted requirements.