There's no really sexually charged questions. The most sexually charged test is toward the end where you're given several ink blots and sort them into sexual and non-sexual symbols. Of course, with tests like these, Kaufmann screws with you no matter how you sort them.
Kaufmann does say "you're clearly not getting enough" during the game (though I think he says that no matter what), and you can answer the questions and use the tests to suggest a very shy, introverted character with little sexual experience. Unfortunately, that seems to net "The Wicked and the Weak" ending (unless you follow it up by being a perv in the game, which would probably tilt the scales back towards the Charlie Sheen ending... ahem, I mean the "Sleaze and Sirens" ending).
Actually, if you just stop and explore everything, you'll pretty much definitely get the Love Lost ending. I'm pretty sure the therapy sessions don't affect the ending at all, only what you'll be seeing in the next area.
Actually, I explored everything and got Wicked and the Weak the first time. I ran through a second time focused only on the essential tasks while also answering the therapy questions as an extrovert, and that lead to Love Lost. The walkthroughs and other wikis back that up: introverted answers in the therapy sessions have the same effect as being rude to the characters, to the point that even being nice to the characters doesn't override it. According to most sources, exploring is bad for the ending because the game interprets that as being unfocused and "easily distracted by trivial things.
I answered the psych questions about being generally introverted and inexperienced and was generally decent and kind where possible in the playable sections, and while the early game definitely seemed to be aiming for Wicked and Weak at first, it started to changed at by the halfway mark it had shifted to Love Lost instead. I looked at pretty much everything there was to look at, so although that does have some effect, how you treat people seems to have more.
For what it's worth, I answered the survey inexperienced and introverted too, but I was headed for the Love Lost ending from the beginning. I don't know what else it takes into account, but it's definitely possible; I tried to do different things and answer the questions differently for three more runs through the game, but I ended up having to look up a walkthrough to figure out how to get any of the other endings.
Meta-reason? Because the game's set up to make it seem like you're playing Harry, and apparently in this universe Harry does indeed make up half of Cheryl's genetic code. Bit hard to get away with that sort of manipulation when you allow something like *that*....
Pretty fly for a dead guy
If Harry is really Dead All Along, then how can he still speak to/frighten the people who live at his old house? Hell, how can he speak to Cybil, Michelle, and Dahlia? If this is all just Cheryl's delusions, how can other characters interact with Harry? Dr. Kaufmann seems to be the only character in the game who CAN'T see Harry. There's got to be some point to that...
Maybe Cheryl is (still) psychic, and he was a physical construct somehow willed into being by her, along with the monsters? By the way, you don't see that Kaufmann doesn't see him at the end - after the camera pans to Cheryl and Harry, we never see him again. He might well be shitting his pants while the whole scene is unfolding.
It's pretty heavily implied, if not obvious in some cases, that all the people Harry talks with are also constructs. "Dahlia" isn't equivalent to Dahlia Mason, Michelle and Lisa are from a sex tape that was created 18 years ago and haven't aged, everyone seems to know things they shouldn't and act inconsistently, basically acting however the psych profile and Cheryl's wishes require, and they are a part of the Otherworld, freezing with it when it shifts to the Nightmare. Kaufmann and Cheryl are the only real people.
You're assuming that the sexy times ending is the real one.
There are basically two ways to interpret what's going on. One is that the events of the game, save for the Kaufmann sessions, are all inside Cheryl's head. Harry isn't really interacting with anyone, because the whole thing's her fantasy world; they're all equally imaginary, in a story scripted by Cheryl's mind. The other way is that Harry exists and he really is exploring the town, but he only exists because Cheryl believes so strongly in him (sort of like Maria in the second game). He seemed real to most of the characters in the game, but by the time he gets to Kaufmann's office, he's already fading away because Cheryl's either facing reality or retreating entirely into her mind.
The second interpretation ties in nicely with the fact that if Cheryl rejects treatment and continues to believe her father was a hero in the end, Harry doesn't freeze and shatter; he still exists, because Cheryl persists in her delusions regarding him.
Word of God says that whatever interpretation sits best with the individual player is the "true" explanation. Regardless, each character does seem to be either a construct representing something out of her psyche or actual people from other memories cobbled together in a Frankensteinian fashion into Harry's "story." Or both — if you believe the phone messages are about Cheryl, then it's possible Cybil, who's forty in the game, was the arresting officer when she murdered that mall cop as a teen; depending upon how you play, this Cybil was either sympathetic or a hardass. Lisa might be a nurse from her past, or the other party in the car accident that killed Harry. Michelle is obviously from her class, and Dahlia is mummy dearest.
Cheryl's hot for teacher?
In the highschool photos, Cheryl and her teacher were really making out?
Since we don't get any information about them outside of the gossips, who are obviously deliberately trying to smear her name (see: trying to make sneaking a photo of her in the gym shower out to be something tawdry on her end), it's up to you how you read the photos. The one thing that's definitely true is that he was holding her in the first one, you can just see his hand on her back if you look close enough, but there are thousands of other fictional teachers out there who've hugged their students without it being anything other than a sign that they're a good teacher who cares about their students. Personally, I always think her pose looks most like she was just caught in the middle of crying on him.
And if you think about the car photo, if we assume they moved to Simmons Street while or before Cheryl was in high school, she might need a ride to and from school. Based on her characterization, she seems to have few if any friends, doesn't seem to date a terrible amount, and based on how Dahlia acted when you meet her in game, she seems to have possibly taken up drinking since Harry died (maybe on that one, not really sure). So it would seem that teacher was some kind of family friend or something.
Seems to me there's a good chance that that teacher is the guy who tells her how much he likes her pigtails and drivers her to school.
No, that guy's talking to his real daughter (at least, he refers to himself as her dad in some versions of the dialogue). The implication is that he was going to a prostitute and making her dress up in pigtails so he could play out his fantasies about his daughter. Yeah.
That doesn't mean he's not her teacher... it just means the teacher is a much, much bigger pervert than we realize.
What? He's dropping his daughter off at school. There's no indication that he's even a teacher, much less that teacher. If the only evidence to support it is that "we don't specifically know that he's not the teacher," then any male character referenced in the game could fit that bill.
Lisa and Michelle? Never heard of them!
How did Lisa and Michelle appear in any game with an ending other than Sleazy and Sirens if Cheryl had no way to know them?
I sorta just assumed the Lisa and Michelle constructs are just random people she met that sorta just evolved for specific purposes in her twisted little psyche. Michelle was from her high school, and Lisa was a nurse from the hospital where she was being treated from cutting herself. Either that, or all the videotape endings were canon to some degree.
But you also have to remember that Harry didn't remember too much. He didn't remember Dahlia, who is his ex-wife and his daughter's mother. The Harry you're playing as was constructed in Cheryl's mind to be the "perfect dad." Why would her "perfect dad" remember the women he cheated on her mom with?
Michelle claims she attended Midwich High the same time as Cheryl (I think that's consistent no matter what you do), and shows Harry her picture. Lisa is iffier, but she might be the nurse that tended to Cheryl after she hurt herself (see the messages before and after the hospital puzzle).
Spitballing, admitted bordering on WMG, Michelle could have been a babysitter for Heather. She wouldn't be the first high school student to do some babysitting for a few bucks, particularly for a Prom Dress or something. That would place her in a point where she would know both Cheryl and Harry in a form she'd be seen in Silent Hill AND in the video in Sleaze and Sirens. Lisa could possibly be the nurse that helped patch Cheryl up after she cut herself in the Cabin, unless I have the timeline wrong...or could even just as simply be a friend of Harry and Dahlia's.
Heather? Who's Heather?
The main page makes a few references to "Cheryl/Heather", but unless I'm missing something, the game always calls her Cheryl. Is this some kind of reference to the first game? The only other one I've played is number 2.
When Harry "hacks" the principal's computer, you can see the Heather part of her name.
It's a reference to Silent Hill 3. Cheryl (although not the same Cheryl as in SM, technically, due to the Alternate Universe thing) is the main character, but goes by the name Heather for the whole game except the very last part.
No Mention of the Monsters?
How come Harry doesn't ever bring up the Raw Shocks in conversation with the various NPCs he meets? He just outran some from the High School, and once he runs into Michelle, he only mentions he needs to get to the apartment. Hell, if I were in his shoes, I'd be like "Dude, what the frick were those pink things chasing me?".
And would you then add "Oh yeah, and why did the whole world suddenly freeze and get covered with ice"? Harry didn't mention it because he thought people would call him crazy. Heck, he probably thought he was going a little crazy himself. I mean, if you were walking along a (reasonably) normal street and suddenly everything froze in time and got covered with ice and then monsters came out of nowhere and started chasing you, wouldn't you question your sanity?
When the school turns into the nightmare after meeting Michelle, Harry shouts "no!" and then says "what's happening to me?", so it does sound like he thinks he might be going crazy. Before that, depending on how the game's played, he'll start to bring it up with Cybil on the phone. When she asks where he went after the forest, he might reply with "I was, well... I don't know where I was." She doesn't follow up on it, but it does suggest that he doubts himself enough that he assumes nobody else would believe him. Plus, he was created as Cheryl's idealized, The Determinator image of her father; he can't help but be single-mindedly focused on finding her, because that's how she sees him.
Public Phone Number?
How did Lisa and Michelle get Harry's cell phone number? It was explained that Cybil got his number because she had his wallet, but Harry never told Lisa and Michelle his number and I doubt Cybil somehow got a hold of them and told them.
If the whole game's happening within Cheryl's mind, or Lisa and Michelle are projections, then the answer is just that that's how she imagined it and their giving Harry phone calls when they shouldn't know his number is a hint that none of it's real. If you take it as really happening but Lisa and Michelle are Harry's lovers as "Sleaze and Sirens" suggested, then... well, that gets into Voodoo Shark territory. If you take what's happening as more or less real, Harry probably gave Michelle his number during the period when he thought she'd been replaced by Dahlia (their phone conversation in the mall suggests that Michelle saw a different version of events, but the call disconnected before Harry could learn more). Lisa's a little weirder: maybe her panicked phone call for help wasn't a normal call at all, but a psychic effect like the ghost/memory messages since she was so close to death. That'd explain why her phone call sounded so surreal and static-filled compared to one of the normal calls.
Lisa also asks about Harry's daughter without him ever mentioning to her that he has one. It's supposed to be strange, this is Silent Hill after all.
I noticed that too, and after a few playthroughs found something that might explain it on a meta level. There's two conversational tracks Harry can follow while walking with Lisa. In one of them he mentions his daughter very early on, and Lisa's comment follows up on that. In the other, he doesn't bring her up, but that exact same follow-up comment from Lisa happens anyway. It could just be a glitch that's keeping her from saying whatever she'd say otherwise, or the developers overlooked her comment during the writing process. On the Watsonian level, though, yeah, it can just be taken as part of the overall weirdness of things.
How much do you take for murder?
Cheryl seems still pretty young in the last scene even though she murdered a security guy in the mall. How did she get out of prison that fast?
Most likely, the courts determined that she was mentally unstable at the time.
What's With All the Pictures?
What's with all those photos you can take that trigger events that have nothing to do with Cheryl? The abused boy hunting with his father or the boys in the water treatment/sewer place? The later messages all seem to center around a teenage girl who gets into bad situations (the girl who gets date-raped in the car, the shoplifter, the girl who's prostituting herself and dressing in pigtails and getting driven to school by her john, etc) but that doesn't really explain the boys.
It's another one of those things you can take two ways. Some of the stuff might have happened to Cheryl herself, like the date rape and the shoplifter, and maybe the party in the woods (though depending on how you play it, the party in the woods can lead to the girl drowning, so maybe not). If it's all happening in Cheryl's mind, then even the unrelated stories are imaginary allegories about Cheryl, reflecting her own feelings (the brother who died in the plant reflects her survivor's guilt, the John reflects her distrust of men and so on). That's probably the simplest explanation. Personally, I like to think that Harry's a mental projection who actually came to life one fateful night, like something out of The Twilight Zone. Under that theory, since Harry's a sort of spirit himself, he can sense and interact with other psychic hot spots and restless spirits that are haunting the town. Some of the stuff might be Cheryl's memories, but others could be unrelated crimes and tragedies that have left their own mark on the town.
The Joel Jr. ones are the ones that confuse me the most; there's the kid who accidentally hanged himself, the girl who drowned at the party, the kid who took pills in the woods, the boy who was killed in the treatment plant, but what happened to Joel, besides that his father forced him to kill an animal? All of the other instances are things that Cheryl could have at least heard about in high school after Harry was killed, but the Joel Jr. ones are about a kid and his jerkass father— even if it was just a concoction of Cheryl's mind, why would her mind even create such a horrible monster of a dad? If it wasn't, how would she even know about that incident?
Well, depending on how you play the game, Harry himself could have been a perhaps physically abusive alcoholic, or a completely uncaring womanizer. That might have something to do with it.
Cheryl has obviously visited this forest multiple times, both as a child and as a teenager. She probably witnessed the Joel Jr. stuff. Maybe she was friends with them as a child.
I'd think correlated symbolism. Like how Joel Jr's first kill was the deer, Cheryl's was that guy in the mall she killed. Given that the world is a reflection of Cheryl's mind, that's the best answer I can come up with.