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I'm now convinced there are actually multiple ways to go about that, but if I don't work the energy to actually make a guide, seeing there are none at the moment, here is the route I followed from memory(some spoilers, so advert your eyes if you don't want to be spoiled):
First day:
-Went with the cute brunette with the dress(The Boy). Do everything you can to get the votes while minimising the suspicion. Always wait as much as you can before making a choice, when a choice is starting to grey out and you consider it your best option pick it. Always go for the votes.
If memory serves me well, you should be able to do 2 of his scenes the first day.
-Rest of the day, spend with the Slut and the Photographer. When prompted to make a choice between them, take the Slut.
The reason for that is while the Photographer is popular, the the Slut is even more popular so has access to more votes. In practice it means her scenes just give more voices and do so faster than the Photographer will.
-Spend the first night with the Stalker. That will give you 3 additional votes. The Stalker is the best first night option, as you should have, I think, 2 suspicion max at that point(one being unavoidable).
Second day:
-Do one more scene with the Boy, where he will steal your phone.
-Start working on the Slut again, make everything to get as many votes out of both her and the people she's with. Don't bother too much about suspicion.
-Normally, you should be at 3 suspicion at that point. That night, visit the Beauty. Your suspicion will go away.
Third day:
-Morning should force you into The Boy scene, after he stole your phone. This is actually a boon for you. A lot of people seems to think it's not, but it really is, if you play your cards right. The trick is when confronting the President to pick the "blackmail" option. This will unlock two options further in the conversation, which are blackmail or deceit. Both lead to you getting 4 more votes from the President.
-Finish the Boy, and squeeze him for votes as much as possible. This should lead to something like 6 more votes.
-Keep working on the Slut. Go up to the fourth scene with her(may need one more day). If you need the achievement, save before doing the last one, as it's pointless, then reload. One of her scenes is a whopping 11 votes worth. You want that.
-For the night, I went with the Beauty despite having 1 suspicion only. I think this is important because I know it radically change some dialogues options as well as your look(you get a collar). The whole fact you are with the Beauty is what I think is a flag to allow some things.
Fourth day:
-Finish the Slut, if it's not already done.
-Start to work on the President. Normally, that part of the story is accessible as the Nerd's part if you went with the introduction to her(with the Athlete). But it requires one more scene to do so, which you won't have the time for.
-Normally, at that point you will have low suspicion, which allows you to choose which path you really want to take. If you want to go with the Beauty path, pick her despite not needing it. If you want to go toward the Ladykiller route, go for the Stalker again. At that point you will have 2 nights with both equally.
Fifth day:
-Finish the Slut if not already done.
-Keep going on the President route.
-Sleep with whoever you want.
Last day:
-Normally, your last action of the day will be the Nerd asking you for a favor. Agree to help. You don't need to ask what the favor is, you won't need that information. Tease the Nerd in front of the Photographer to get an extra vote from the Beauty. Ask the Photographer to deal directly with you, and do what she asks in exchange. When the Nerd will ask later to give her the votes you were supposed to get for her, just keep them.
At that point you should have way more than 50 votes anyway, and you will get confirmation that you are winning even before that when the President confronts you to ask for your votes.
To recapitulate:
-All of the Boy's route(blackmailing or deceiving the President)
-4 scenes of the Slut's route after having chosen between her and the Photographer(Get all the votes, all of them).
-3 scenes of the President(trick the Nerd)
-At least one night with the Stalker.
-At least one night with the Beauty to wipe suspicion.
A few tips in order to get the most out of people without raking too much suspicion:
-Always try to wait for the best options possibles to appear, until what you think you really want to answer is getting greyed out(about to disappear). If you have the choice between being terrible and being suspicious, be terrible. This is in character, your brother is a huge jerk, you are expected to act like that. Do not be the kind of person who say yes and try to be nice with everyone... You shouldn't be.
-A sharp wit is what people expect from you. That means the right amount of cutting must be done. Being a bit harsh/mean with your friend is pretty normal in friendly conversations, call that friendly banter if you will. Being too compliant or silent is highly suspect and you will be penalised for it.
-The Stalker and the Athlete are probably the only honest and friendly persons around. All the others have their own agenda and will try to use you for it. Knowing that, don't get any remorse at playing them and taking advantage of it.