Keep trying! The nicer you are, the more likely it’ll happen. EDIT: Another thing to note: options that support Olivia will make Madison like you more. So if you have an option to take Olivia’s side and to patch things up between them, do it!
EDIT 2: Sooo… I played through with all the pro-Madison choices that could have possibly been selected. I ended up a single percentage point below the check needed to kiss her. Funnily enough, MC mentions that they’ve been nice to Madison all night - you literally have to be nice to Madison all night to kiss her! So, with that being said, I’ve lowered the Madison kiss check to 45 instead of 50. This should make it a bit easier to get her to kiss you.
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oh, I didn’t know it was an actual option…replay time 
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Baam
261
Highest I can get though is like 36%. WHAT AM I MISSING @trevers17
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You have to pick every pro-Madison choice, and you can’t send her away at the beginning. You also have to support Olivia and Jordan.
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I made it to 41% with her right before spin the bottle, but wasn’t able to reconcile Jordan and Olivia (since I talked to Madison by the fire to make her go up), then I reloaded and went back with Olivia to help her reconcile and only got to 37%, then when I reloaded the last time my save glitched and saved in the stats screen so I have to start from scratch again 
tldr: I didn’t make it to 45 lol rip
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Okay, tomorrow I’ll drop it down to 40 and then we’ll see if that’s possible.
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I did all of that and reached 37 
, how do I make her kiss me, or reach 40?
I think I’ll just compile a list of every single choice you have to make, just to make it easier.
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Okay, I updated the demo with the new stat check for Madison’s kiss (40). I also decided to add an achievement since people are so interested in seeing this option and it’s so hard to get lol.
If you don’t want the challenge of figuring it out yourself, here’s the choices you should make to get Madison to kiss you during Spin the Bottle.
Madison Kiss Guide
Chapter 1
- No way. I’m just gonna let her ruin her own night. I’ll just talk to the others instead.
- I’ll just keep my distance. I don’t feel like fighting tonight.
OR
I’d like to make up, or at least lay the groundwork for forgiveness.
- I would love to have a tight friendship with both of them again. I miss my childhood friends.
- I suck in breath through my teeth and look down. “Uh, FYI, some people here are on the Pep Squad.”
- Olivia is right, we need to stay together. “It’s not safe to be on your own. Don’t put yourself at risk.” (This is actually a -1, but it keeps her with the group, which gives MC the opportunity to boost their relationship more)
- I’ll… sort of tell the truth. “There was an event that tore us apart.”
OR
Jesus, here we go again. “Just mind your business, please.”
- “I want to. I do miss having her as my friend.”
- I criticize him for acting weird right out the gate.
- I get up in his face and call him out. “You need to be nicer, or you can kiss the free beer goodbye.”
Chapter 2
Sabrina Chat
- I do. Madison deserves some support. “I think that’s a great idea. Go for it.”
Madison Chat
- You know what? I’ll chat with Madison. Why not?
- “Relax. I come in peace.” I don’t think being rude is worth it at this point.
OR
“I know I’m awful, but I want to talk to you.” Self deprecation can surely break down her walls.
- I’ll try some kindness. I can’t fall into her trap. (All options in this choice tree reduce her relationship, but this one only does it by 1.)
Rest of Chapter
- Oh, I’m definitely eavesdropping on her. This is a good opportunity to learn more about her.
OR
I hate to listen to others’ conversations, but I think it’s necessary if I want to patch things up. (Does not affect relationship, but opens the eavesdropping route, which does.)
- I’m not mad about it. I understand why she might want to hash it out with someone. But why Jordan?
- I’m really, really hurt. I hope I can change her perspective and show her what happened was an accident.
- This doesn’t make sense. “If you were worried about her lashing out at me, why did you invite us both?” (Opens another choice tree for next option.)
- Really stressed. I need to show Madison that we don’t need to hate each other.
- Olivia’s right. Jordan clearly didn’t listen to her. “Dude, just get away from there and let’s go.”
Chapter 3
Beginning
- Helping? Uh, no thanks. I’m gonna sit by the fire and start drinking.
- I look at Madison. “He’s being genuine.”
- Madison’s right. “Yeah, this spot is only good when there’s not many people here.”
Carlton Flirt Scene
- I’ll give her what she wants in return. “Help me now and I won’t bother you for the rest of the night.”
- Sabrina. She’ll have the best reaction.
- Let’s make a huge scene. Go big or go home.
Sabrina/Jordan Interference Scene
- I want to help them get together.
- (If Madison confronts you at the end) Be honest. “I was trying to help them.”
- (Madison’s confrontation will be interrupted by Adrian if the player chose to have Adrian protect them from Madison. This means the player neither gains nor loses any relationship points with Madison.)
Olivia/Madison Scene
- “Fine. Let’s just make smores then.”
- Madison doesn’t hate her.
- Say nothing.
- That’s what I want too.
- “Madison’s going through a tough time. She needs your support.”
- I don’t really want Olivia on my side anyway.
- Madison needs to know how Olivia feels. “Olivia is worried about your relationship.” (All choices in this tree reduce relationship points with Madison, but this is the lowest reduction and helps fix their relationship.)
- (Automatic +10 if the player fixes Olivia and Madison’s friendship)
Jordan/Carlton Fight Scene
- (This scene only opens if you talk to Jordan at the beginning of Chapter 3 and choose [I’m curious. “Not saying this to be mean, but I’m actually curious why you came.”], which means you miss a few boosts with Madison. You also have to find out from Carlton in Chapter 2 that he blames Jordan for his bullying.)
- Even though Madison isn’t the nicest friend, she’s got a point about Carlton.
- Agree with Madison. “Confront him.”
Spin the Bottle
- If I give her an out, she’ll want to play.
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Baam
269
It seems the update crashed the save system.
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Vyndral
271
Woot! I needed a helping hand. I tried several times last night and the highest I could get was 26. I know sad.
It is funny I see using the save system and checking how answers affect stats as cheating. Yet I’ll jump right on a guide. Odd imaginary rules I have for cheating in my head.
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Oh my god, I just noticed that MC have an avatar. What a jock.
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Wait until you see the official art! 
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During this part of the Madison kiss guide:
I don’t know if I just didn’t unlock the option, but the part where I assume this dialogue should come up, it doesn’t
Also, again it might be me just screwing up, I talked to Carlton about Jordon, then to Olivia about her mom, then told her about his bullying, but they didn’t reconcile. Do I have to have a good relationship with both of em for this to work?
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The Madison guide issue is my fault. That option only comes up if you bring up Madison’s fighting with her at the beginning of the chapter.
For the Olivia/Jordan issue, did you also attempt to patch things up between Madison and Olivia? You don’t have to succeed at it but you do have to try. You need to do all four things to succeed.
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Wow okay, thanks for bringing my dark side out xD tbh, Carlton’s hand-kissing at the beginning put my quite quite off, because it is indeed weird and ridiculous, so at first, I wasn’t interested in this jock boy. And then my bff told me that he is interested in Carlton? Sure, have him I don’t care. Now, if my best bro had left it at that, all would’ve been fine. But then he turned a real bitch and wow the deep, dark, evil part of my soul reached out and went: I will romance this boy just to hurt you then. XD maybe that’s why I like Madison so much. And Carlton, ignoring the whole hand-kissing, is quite yummy. Thank you for the option to dominate him btw, there is not enough game giving me the option to do that.
And amazing writing, these characters actually make me feel, react, and do things with an intention behind. I can’t wait for more.
Would you consider a tumblr or discord btw?
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That is so delightfully petty! 
I’m glad to provide! I always notice people saying they’re tired of being in the leading or following position when it comes to sexy time stuff in CS games, so I wanted to fix that.
That is so very nice of you! 
Unlikely that I will do a Tumblr as I don’t have fond opinions of that site lol. As for Discord, I thought about it a while back, but there wasn’t a huge enough response to warrant me making it. If my games start getting wildly popular then I might consider a Discord.
Hey everyone! I know some of you might be wondering how progress on Chapter 4 is going since it’s been a little over a week since Chapter 3 dropped, so here’s an update. I’m writing Chapter 4 now – currently at 3.5k words – and I’m also laying out the various branches at the end of the previous chapter. Like Chapter 3, this chapter has a lot of variations based on your previous choices – unlike Chapter 3, it has no open-ended discussion section and the entire chapter is much more linear, with specific events occurring in order based on where your MC stands with each character.
In terms of the ROs, I just finished setting up the branch variations. Each RO requires a specific set of decisions to activate their romance route in Chapter 4. If this is not activated, then you won’t be able to become official with that character and they won’t be interested in you – if that happens, they are either with their other romance partner or they’re just on their own. If they’re with their romance partner, then you have the chance to either break them up or help them to become official, if you want to. For Adrian and Carlton, not getting involved will result in them becoming official; for Sabrina and Jordan, they won’t get together. Your previous actions heavily influence your success rate in breaking them up or getting them together, so keep that in mind when replaying.
Since the romance routes are going to require a lot of specific actions, here’s an exact list of requirements to unlock the romance route for each RO.
Romance Routes Information
Maintaining Friendship (required for romance routes)
Adrian
- Do not kiss Carlton in the woods during his flirt scene.
- Keep your relationship with Adrian at or above 15.
Carlton
- Do not tell Carlton off for trash talking Adrian during the former’s flirting scene.
- Do not tell Carlton you aren’t interested in him anymore during his flirt scene.
- Do not encourage Jordan to confront Carlton.
- Keep your relationship with Carlton at or above 15.
Sabrina
- Do not let Sabrina find out that you’re flirting with Adrian or Carlton. This can be easily avoided by not selecting Adrian or Carlton’s flirting scenes in Chapter 3.
- If you do select those scenes, you have two options to prevent her from finding out.
- Flirt with Sabrina after flirting with Adrian and/or Carlton: Don’t ask for her help with distracting Adrian/Carlton or don’t admit that you’re flirting with them when asking her for help.
- Flirt with Sabrina before flirting with Adrian and/or Carlton: Don’t make out with Carlton in the woods
- Keep your relationship with Sabrina at or above 15.
Unlocking Romance Routes
Adrian
- Meet all conditions for the Adrian friendship route.
- Flirt with Adrian and make him like you more than Carlton.
- Get Adrian to say he wants to talk to you alone.
- Do not embarrass Adrian during the interference scene. (This means not choosing “I want to ruin their relationship” at the start of the scene, or not choosing the scene at all.)
Carlton
- Meet all requirements for the Carlton friendship route.
- Flirt with Carlton and make him say he likes you more than Adrian.
- Get Carlton to say he wants to talk to you alone in his flirting scene.
- Do not tell Adrian that Carlton was trash talking him.
Sabrina
- Meet all the requirements for the Sabrina friendship route.
- Flirt with her and get her to say she’s more into you than Jordan.
- Get her to say she wants to spend time alone with you.
- Talk to her about her home life. (You don’t need to succeed in getting her to tell you about it.)
On the non-romance side, your choices will also influence who you’re friends with at the start of Chapter 4. This will affect whether characters support you or undermine your arguments with Madison (which are key in this chapter, since it’s when Madison finally confronts MC about what happened a year ago!). They will also behave differently towards you depending on how you’ve treated them thus far. The only person who will always treat MC the same is Madison, for obvious reasons.
Because of the complexity of the relationships and the different actions influencing the outcomes of Chapter 3, I’m going to go back and add some identifiers for key decisions. These will be Telltale-style messages that indicate a choice you made will have an impact later. While this won’t be extremely helpful, it should help you make decisions in-line with what you want from each character.
Hopefully that gives you all a bit of understand about where this chapter is headed. I’m really excited that this game is nearing completion – what I have planned for the later chapters when shit goes awry is seriously so exciting to me that I’m going to try and blast through Chapter 4 as quickly as possible. I hope you all love what I put out, because I definitely do!
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