How about that.
Jill is super shy and she has only one friend, who is Bella.
She had some dates and kept Tybalt on safe distance, no problem, but then BAM here comes our boi Tremolo.
Fucks her up mentally, make fall in love with him. Like Cathy, Jill is so brain damaged, she does ONE stupid thing in the game, she agrees to Tybalt's 3 dates JUST to protect her lover. I repeat, she did not do a single stupid thing before that, she is just to into our Alpha Dog.
Regarding her easily making a new friends out of Josy. It is simple, Josy is so easy going, she makes friends even with shy shy Jill. After that Jill is also having fun with nerds, but this only happens after she meets our hero and Josy.
Sorry, no drama and mindfuck