Maybe the game is giving you a warning you're ignoring ...
I mean, really mate ... when a professional confidante, a personally trusted psychological counsellor, can double-cross not only a client, but a supposed friend, and deliver her into the evil hands of the MC (aka M*d Seri*l R*pist) ... you really think craftily sidling up to a she-devil so devious, so damn vicious is a good idea?
Try hunting down that one, and you'll be lucky to avoid getting grabbed, drugged, trussed upside-down like a plucked turkey & your gonads illuminated to high heaven - electrocuted with industrial-standard generators - by the Headmaster's revenge-seeking gang.
Or possibly by Linda. Or even Judy's gigolo, Bob (who - don't say you haven't noticed? - wears a cunning disguise of wig, beard and corset (and decent clothes) whenever he's playing the Headmaster-Godfather of all the vice in the game. You didn't see the join??).
I'd stick to Sarah, if I were you.
(Mind you - you do know Sarah & Macy are Judy's agents too, don't you?)