Claudia Wolf - Claudia is the lady Heather meets after exploring SH for a bit. Heather asks the lady if she was the one responsible for all of the monsters, etc. Claudia then proceeds to feed our poor heroine cryptic lines of BS... about 'paradise' and 'blood-stained hands' and such. She later sends a monster to kill Heather's father, Harry Mason. After that Heather wants Claudia dead.

Douglas Cartland - He's a detective who asks Heather for her attention. He has something important to tell her about her birth. [What? Did her mother die of "that damn disease" like James and Harry's wives?! O_O] He's there for her when her father dies and helps her along when she gets to Silent Hill. Douglas says that Heather reminds him of his son, in certain ways.

Vincent - Heather thinks Vincent is off his rocker. She proceeds to listen to his rants and then says he's just like the rest of them. Insane.

Stanley Coleman - After reading all of Stanley's diaries, Heather thinks he is a nasty pervert. :P I feel bad for Stanley... he seemed like he really loved Heather too bad...

Leonard Wolf - ...is in the way. When Leonard first contacts Heather, he thinks she is his daughter, Claudia... but when he finds out she's not he asks for her help. She goes to him, and ends up finding out he has cryptic lines of BS for her too, just like Claudia. They fight. Heather kicks his ass, and takes his seal.

Harry Mason - Heather loved Harry like he was her true father. She sticks up for him many instances in the game and seeks revenge when he is killed. The scene where she drops her head on his blood-stained lap and cries is very emotional, and shows just how much she thought of her father.