This could be due to dialog changes in the walkthrough mod, but I am not aware of how they have changed things. It could just be our original content, but if you figure out if it is us I'd like to hear what you think is awkward/weird?
I know this is a reply to an older comment...
I kind of feel the same about the game getting "awkward/weird", and it has nothing to do with the writing being awkward or weird (actually, the opposite)... but the thing is... the game kind of encourages you to engage with as many women as possible, yes, you can reject everyone or pick and choose, but the game is long, REALLY long and rejecting too many characters can make for a somewhat lackluster experience. I also had the hardest time to even reject one character, since the game kept throwing her at me again and again and AGAIN, even though I wanted nothing to do with her. So I had to keep refusing her advances but still keep things friendly with her, which can get a bit tedious.
But if you don't pick and choose only a few characters you - the player - may eventually reach a point where all the more or less honest declarations of love to all those women will make you feel very uneasy, because this game is NOT a harem game and you will eventually have to break up with several or almost all of those women whom you told in so many words that you're very serious about them. In short: it makes you feel like a complete asshole. Not because the writing is bad, but because you, via the MC, have become a sleazeball that romances everyone and who plays with the emotions of the love interests who (kind of) believe you are their only one. I mean after the first romantic beach house scene with Katie... (and if you like her of course) it gets increasingly difficult to keep engaging with the other women... but if you don't... things can get very boring, because Katie only has so many scenes and is absent for long stretches (like all the other characters).
I feel games like WTHI would greatly benefit from either... being a true (silly) harem game (but that is usually very unrealistic and I actually appreciate the approach here!) or having far fewer potential love interests that make an (eventual) solo route something that is worth playing. If someone solos Debbie... good luck, you will have to read entire phonebooks worth of dialogue and will have entire episodes with zero scenes. That usually does not make for a satisfying experience. Debbie is an extreme example, but even a solo Katie route will result in long stretches of zero scenes with her.
In other words, depending on what kind of person you are romancing almost everyone in this game will make you feel very awkward and weird, because it is not alright, it's very wrong actually. If you don't project any emotions into the game and characters and treat them as the imaginary pixel toys they are it's certainly different.
I will probably resort to to the schizophrenic tactic of engaging with as many women as possible (the ones that I like - so that the actual game doesn't become too boring for long stretches) and when complete disaster falls upon the MC I will just restart the chapter where things begin to turn south and set the variables so there is a Katie (or maybe Debbie) solo path. But playing like that is actually awkward and weird.
Too many VNs have this issue... too many love interests, solo paths punish players with lack of scenes or lack of content, so you are heavily encouraged to catch 'em all until you have to make a decision... but that can easily make someone feel like a complete douchebag if you'd rather actually be on a solo path, ESPECIALLY when it's not a harem game. And extremely long games like WTHI suffer from this issue a lot more. I want to see the poor person who has the mental fortitude to play a Debbie solo path without ever fooling around with anyone else (unless it's mandated by the story or a requirement to get to Debbie) and won't die of boredom or utter despair.