The whole Jill blackmail thing would make way more sense if she acknowledged she was giving Tybalt his 3 dates not because she thought there was any real legal threat, just that it was the path of least resistance. It’s a relatively minor thing to go on what has been, so far, one trip to the mall and a tennis match.
She could acknowledge the MC has made some bad decisions lately whilst also knowing that whilst Tybalt doesn’t have a leg to stand on legally, he’s clearly serious about fabricating some sort of inconvenient bullshittery for the MC. From there she could take the position that it’s just easier to do this relatively minor thing (3 dates) to keep Tybalt off MC’s back.
As it’s currently setup there’s fuck all to stop Tybalt just extorting more dates or going to the police anyways when hes rejected and she dates the MC publicly. Plus it makes Jill seem... stupid and kinda weak that she’s giving into this silly blackmail.
At least if she was just playing along to keep the peace and cover for the MC’s shitty decisions in hell week she would have calling Tybalts bluff to fall back on.
It flows better if Jill’s motivation is giving Tybalt what he wants to save the hassle of disproving his blatantly ropey blackmail. All the blackmail fun, none of the characterisation damaging implications.
and if you really look like Lana (I doubt it 
