Courtesy of member 262177:
"Firstly, you must skip at least 3 classes AND sleep at least twice to trigger the initial interaction where she'll warn you.
She will also only catch you on a Wednesday afternoon after class, and in her dorm room in the evening for assignments.
(You can give the assignment to Ms. Hobbs on the couch if Ms. Macky isn't there, or leave it on her dorm room table.)
Might as well add the rest (0-indexed and starting with 1 for clarity, with 1 being your first meeting on the third day.)
Interaction 2: 6+ classes skipped, 3+ slept.
Interaction 3: 9+ classes skipped, 4+ slept.
Interaction 4: Turn in exactly one assignment. Hopefully the switch is checked in her dorm room as well or this one will break your progress and prevent you from progressing any further.
Interaction 5: Turn in a total of exactly two assignments and trigger the first shoe event. See above.
Interaction 6: Turn in a total of exactly three assignments and trigger the second shoe event. See above.
Interaction 7: Turn in a total of exactly four assignments and trigger the third and last shoe event. See above.
Interaction 8: Turn in a total of exactly five assignments, apologize to her and make sure you have 10+ classes skipped by now. If you turn in more assignments before skipping the next class, you're fucked due to how this is handled.
Interaction 9: Turn in a total of exactly seven assignments."
It's really annoying that it's so precise to pull off and while the scenes are incredibly hot, it has put me off continuing to play the game because I have no idea if the rest of the interactions are going to be this precise and easy to break if I do one thing the game does not expect.