There are definitely a growing number of moments when rollin' with Lily that you see emotions developing from her end and slipping through.
Even at the outdoor BBQ, you see a few small cracks starting to form. It becomes very apparent when she says "I can only do the things I do because I don't have feelings for someone" (paraphrased). Over the story she does have, you see her opening up more and supporting MC more. She tells the big story of her background that no one else knows. The pandora's box has already been opened.
Even if you do it the "rough" way, afterwards she comments that the MC almost didn't listen to her and once admitted to, she leaves quickly. So even there, she's realized it's become something else than what she envisioned rolling to be.
Yeah thats the crux for the lily/tremolo relationship.
Tremolo wants more (as he always does) and lily is falling for his charms (against her wishes).
This kinda leaves lily on a crossroads as she has to consider how serious she is about tremolo. And than she has to decide if she breaks up with tremolo or quits her job and takes a student loan.
She wants a great relationship, love and everything but it doesnt fit her plans yet, she wants that when shes done with studying and working in healthcare. Now she has to ponder what to do as she found the possible man of her future sooner than intended lol
And even if tremolo would be able to handle her being a stripper (and lets be honest, our dramaqueen wont be able to handle it when they get serious) she wont be able to handle it herself, its not what she envisioned.