This Midnight Sin walkthrough covers the game’s progression in chronological order, ensuring you never miss a required event, character interaction, collectible book, b*ackmail objective, or stat check. Follow each day exactly as outlined to unlock story scenes, character routes, Fight Club rewards, hidden locations, and progression events while collecting all seven Sin Books and advancing every major storyline.
100% Walkthrough & All Routes
Here’s all the information and details you need to unlock every key story event, character interaction, and scenes in Midnight Sin in this walkthrough guide.
Olivia Introduction
No action is required during the first Olivia scene.
Olivia Choice
When prompted, select:
- Hug her back
Monday
Explore the Mansion
After gaining control of the character, begin exploring the mansion.
Go to the Study and interact with the bookcase. While exploring, examine six paintings throughout the mansion. The final painting becomes available later in the game.
Find the First Sin Book
Visit the MC’s bedroom and click the books on the bookshelf five times.
After discovering the Book of Greed, take it to the Study and place it inside the bookcase.
Kate Conversation
Time: 08:00
Location: Entrance Hall
Speak with Kate and discuss:
- MC
- Victoria
- Kate herself
Olivia Conversation
Time: 10:00
Location: Olivia’s Room
Talk to Olivia about:
- MC
- Olivia
- Madeline
Olivia Pool Conversation
Time: 12:00
Location: Pool
Speak with Olivia and discuss John.
Victoria Pool Event
Time: 14:00
Victoria can be found sunbathing near the pool.
Choose:
- Tell her to get it herself
Collect Partial Payment
Advance time until 16:00 to receive your partial payment.
Pay Off Ruslan
Open the city map and travel to Ruslan’s Office.
Pay off your debt to continue progressing the story.
Victoria Boxing Lesson
Time: 19:00
Go to Victoria’s room and click on her to take her to boxing lessons.
Rebecca Scene
After taking Victoria to boxing lessons, a Rebecca scene will automatically trigger.
Tuesday
Visit the Kitchen
Use the city map and travel to the kitchen.
B*ackmail Event #1
Return to your room and relax.
You will receive the first text message from the b*ackmailer.
Madeline Board Meeting
Time: 14:00
Madeline attends board meetings every Tuesday and Thursday.
Go to her office and click on her.
B*ackmail Objective – Olivia
The b*ackmailer wants you to e*pose yourself to Olivia.
Go to the upstairs bathroom at 19:00.
Olivia Bath Event
Olivia takes her bath at 20:00.
Enter the bathroom one hour before she arrives to trigger the event.
Refill Madeline’s Wine
Time: 21:00
Visit the pool and refill Madeline’s wine glass.
Book of Pride
Time: 23:00
Go to Victoria’s room and click the book on her bed.
Take the Book of Pride to the Study and place it in the bookcase.
Fight Club – Alex
Time: 22:00–00:00
Travel to the Fight Club located in the Mega Mall parking lot.
Defeat Alex to earn:
- $100
- 10 Bonus Points
Wednesday
Rebecca Basement Clue
Time: 07:00
Visit the basement stairs.
Olivia Swimming Practice
Time: 10:00
Go to Olivia’s room and take her to swimming practice.
Madeline Room Access
Time: 15:00
While Rebecca is cleaning, enter Madeline’s room.
Olivia Phone Event
Time: 19:00
Walk past Olivia’s bedroom door.
Madeline Book Clue
Time: 21:00
Enter Madeline’s room.
Before touching the book, examine the painting.
Afterward, click the book located on the ottoman.
Note: You cannot take the book yet.
TV Event #1
Time: 21:00
Go to the living room and watch television with Olivia.
B*ackmail Event #2
Return to your room.
A second message from the b*ackmailer will arrive.
Fight Club – Duncan
Time: 22:00–00:00
Defeat Duncan and receive:
- $250
- 20 Bonus Points
Thursday
B*ackmail Objective – Annabelle
The b*ackmailer now wants you to e*pose yourself to Annabelle.
Go to the upstairs bathroom at 09:00.
Annabelle Shower Event
Annabelle showers at 10:00.
Make sure you are already inside the bathroom one hour beforehand.
Madeline Board Meeting
Time: 14:00
Attend another board meeting.
Fight Club – Sergei
Time: 22:00–00:00
Defeat Sergei and earn:
- $1,000
- 30 Bonus Points
Friday
Shopping Trip
Visit the Mega Mall between 08:00 and 22:00.
Purchase the following items from Sweat in Style:
- Boxing Gloves
- Mouth Guard
- Protein Plus
- Jump Rope
- Men’s Workout Apparel
Then visit Beach Please and purchase:
- Swimming Goggles
- Swimming Trunks
You should have approximately $400 remaining afterward.
Train Skill
Use the heavy bag in the basement at least five times.
Reward:
- +10 Skill
Book of L*st
Time: 16:00
Enter Madeline’s room while Rebecca is cleaning.
Search the following locations:
- Stack of books
- Four nightstand drawers
- Two large pillows
After finding the Book of L*st, place it in the Study bookcase.
Annabelle Art Class
Time: 19:00
Click Annabelle’s bedroom door.
You cannot enter the room yet.
Fight Club – Sergei
Defeat Sergei again.
B*ackmail Event #3
Go to sleep.
A new text message from the b*ackmailer will arrive during the night.
Saturday
Skill Training
Time: 08:00
Use the heavy bag.
B*ackmail Event #4
The b*ackmailer wants you to grab Madeline’s a*s.
Go to the basement at 07:00 and help Madeline with her workout.
Important: B*ackmail events cannot be completed on Saturdays.
Fight Club – Sergei
Fight Sergei once more.
Sunday
Madeline Morning Workout
Time: 07:00
Go to the basement and help Madeline with her workout.
Continue Skill Training
Time: 08:00
Use the heavy bag in the basement.
Learn More About Annabelle
Time: 10:00
Visit Olivia in her room.
Select the following conversation options:
- Ask about Annabelle
- Ask about Annabelle again
- Borrow her laptop
Book of Sloth
Time: 13:00
Go to the Study.
When Annabelle appears carrying an old book, click the book beneath her arm.
Take the Book of Sloth and place it in the Study bookcase.
Dinner Invitation
Time: 17:00
Advance time until 17:00.
Rebecca will approach you with an invitation to have dinner with the girls.
Dinner with the Girls
Time: 18:00
Join everyone in the dining room.
Wine with Madeline
Time: 21:00
Go to the pool and share a glass of wine with Madeline.
Discuss:
- MC
- Madeline
- Any other character
Choose:
- Focus
Although three topics are discussed, this conversation awards only two love points.
Madeline Bedroom Event
Time: 23:00
Enter Madeline’s bedroom while she is reading.
Fight Club – Sergei
Time: 22:00–00:00
Defeat Sergei.
Monday
Continue Skill Training
Time: 08:00
Use the heavy bag.
Watch Cat Videos with Olivia
Time: 16:00–18:00
Visit Olivia’s room and watch cat videos with her.
Defend Olivia at Dinner
Time: 18:00
Join dinner and choose to support Olivia.
Victoria Boxing Lesson
Time: 19:00
Go to Victoria’s room and take her to boxing lessons.
Fight Club – Sergei
Defeat Sergei again.
Tuesday
Continue Skill Training
Time: 08:00
Use the heavy bag.
Madeline Board Meeting
Time: 14:00
Go to her office and attend the meeting.
Another Wine Conversation
Time: 21:00
Meet Madeline at the pool.
Talk about any three topics.
Choose:
- Compliment her legs
Fight Club – Sergei
Defeat Sergei.
Wednesday
Madeline Workout
Time: 07:00
Help Madeline exercise again.
Increase Endurance
Swim laps in the pool at least five times.
Reward:
- +10 Endurance
Olivia Swimming Practice
Time: 10:00
Take Olivia to practice.
Talk to Annabelle
Time: 16:00
Visit the basement and speak with Annabelle.
Dinner with the Girls
Time: 18:00
Join dinner.
Continue Laptop Progression
To obtain Annabelle’s laptop route, continue following Olivia’s hints.
TV Event #2
Time: 21:00
Watch television with Olivia again.
Reward:
- Laptop obtained
Collect the Laptop
Return to your room.
Install H*ntai Impact
Click the laptop and install H*ntai Impact.
Character choice does not matter.
Thursday
Increase Endurance
Continue swimming laps.
Madeline Board Meeting
Time: 14:00
Attend the meeting.
Olivia Bedroom Investigation
Time: 20:00
While Olivia is bathing, enter her room.
Click the book on her bed.
Note: The book cannot be taken yet.
Fight Club – Sergei
Defeat Sergei.
Friday
Increase Endurance
Swim laps.
Attempt to Enter Annabelle’s Room
Time: 15:00
Click Annabelle’s bedroom door.
Kate will prevent you from entering.
Create a Bathroom Emergency
Still at 15:00, go downstairs to the bathroom.
Use the toilet paper roll on the toilet.
Annabelle Workout
Time: 16:00
Help Annabelle with her workout.
Annabelle Art Class
Time: 19:00
Take Annabelle to class.
Fight Club – Sergei
Defeat Sergei.
Sleepover #1
During the night Olivia visits your room.
She brings the Book of Envy.
Saturday
Return the Book of Envy
Go to the Study.
Place the Book of Envy inside the bookcase.
Search for the Key’s Purpose
Travel to the left side of the basement near the washing machines.
Use the key on the locked door.
Investigate the Utility Closet
Enter the newly unlocked utility closet.
Utility Closet Puzzle
You must determine the code for the metal door.
The solution is based on:
- All seven paintings
- All seven Sin Books
Each playthrough generates a different final combination.
Use the following color values:
| Color | Value |
|---|---|
| Orange | 1 |
| Yellow | 2 |
| Light Blue | 3 |
| Green | 4 |
| Violet | 5 |
| Red | 6 |
| Dark Blue | 7 |
Increase Endurance
Swim laps.
Fight Club – Sergei
Defeat Sergei.
Sunday
Continue Endurance Training
Swim laps.
H*ntai Impact Meeting #1
Time: 19:00
Open the laptop in your room.
Meet Annabelle online.
Rewards:
- +10 Gold
- +20 Bonus Points
After paying the guard, five gold coins remain.
Return to the Utility Closet
Time: 22:00
Wait until Rebecca has gone home.
Advance time to 22:00 and revisit the utility closet.
Important: This event cannot be completed on Saturday.
Monday
Increase Strength
Time: 08:00
Use the weights in the basement at least five times.
Reward:
- +10 Strength
S*y on Annabelle
Time: 10:00
Visit the hidden corridor and watch Annabelle during her morning bath.
S*y on Kate
Time: 17:00
Use the hidden corridor while Kate cleans your room.
Victoria Boxing Lesson
Time: 19:00
Take Victoria to boxing.
After the lesson, choose to check on her.
Requirement:
- 25 Skill
Rewards:
- Defeat Devon
- +20 Bonus Points
Fight Club – Sergei
Defeat Sergei.
Tuesday
Kate Pool Event
Time: 09:00
Go swimming shortly before Kate cleans the pool.
Madeline Board Meeting
Time: 14:00
Attend the meeting.
S*y on Kate Again
Time: 17:00
Use the hidden corridor.
S*y on Olivia
Time: 20:00
Use the hidden corridor during her bath.
S*y on Madeline
Time: 22:00
Use the hidden corridor again.
Victoria Dialogue Event
Time: 23:00–00:00
Visit Victoria’s room.
Discuss:
- Victoria
- MC
- Madeline
Wednesday
Continue Strength Training
Time: 08:00
Use the weights.
Olivia Swimming Practice
Time: 10:00
Take Olivia to practice.
Victoria Pool Event
Time: 14:00
Speak with Victoria while she sunbathes.
Cat Videos Again
Time: 16:00–18:00
Watch cat videos with Olivia.
Dinner Choice
Time: 18:00
Join dinner.
Select:
- Keep Quiet
H*ntai Impact Meeting #2
Time: 19:00
Use the laptop and meet Annabelle again.
Ask Madeline About Victoria
Time: 21:00
Share wine with Madeline.
Ask about Victoria.
Select any other two topics.
Choose:
- Compliment her legs
Fight Club – Sergei
Defeat Sergei.
By this point you should possess approximately:
- $10,400 Cash
- 400 Bonus Points
This total includes:
- Devon rewards
- H*ntai Impact squirrel hunt rewards
Midnight S*y Event
Time: 00:00
Use the hidden corridor and s*y on Olivia and Madeline.
Thursday
Continue Strength Training
Time: 08:00
Use the weights in the basement.
Kate Bathroom Event
Time: 12:00
Visit the upstairs bathroom while Kate is cleaning.
Annabelle Pool Event
Time: 13:00
Go to the pool and talk to Annabelle.
Madeline Board Meeting
Time: 14:00
Attend the meeting.
Victoria Selfie Event
Time: 19:00
Visit Victoria in her room.
S*y on Victoria
Time: 23:00
Use the hidden corridor and watch Victoria while she is on her phone.
Friday
Continue Strength Training
Time: 08:00
Use the weights.
Annabelle Workout Choice
Time: 16:00
Talk to Annabelle in the basement.
Choose:
- Allow her to slack off
Cover for Annabelle
Time: 18:00
Join dinner with the girls.
Choose:
- Cover for her
Annabelle Art Class
Time: 19:00
Take Annabelle to class.
Saturday
Strength Training
Use the weights at any point during the day.
Buy Women’s Workout Apparel
Visit Sweat in Style at the mall.
Purchase:
- Women’s Workout Apparel
Cost:
- $275
Sunday
Annabelle Workout Choice
Time: 16:00
Help Annabelle again.
Choose:
- Allow her to slack off
Dinner Choice
Time: 18:00
Join dinner.
Choose:
- Tell the truth
H*ntai Impact Meeting #3
Time: 19:00
Use the laptop and meet Annabelle again.
S*y Event
Time: 00:00
Use the hidden corridor and s*y on Annabelle and Madeline.
Monday
Annabelle Modeling Event
Time: 14:00
Go near the arboretum.
Choose:
- Sure, why not?
Requirement:
- 50 Strength
Annabelle Workout
Time: 16:00
Help Annabelle exercise.
Victoria Basement Event
Time: 20:00
Talk to Victoria while she practices boxing.
Tuesday
Victoria Kitchen Conversation
Time: 08:00
Talk to Victoria.
Discuss:
- Victoria
- MC
Annabelle Kitchen Conversation
Time: 11:00
Talk to Annabelle.
Discuss:
- MC
- Annabelle
Madeline Board Meeting
Time: 14:00
Attend the meeting.
Victoria Boxing Training
Time: 20:00
Help Victoria with boxing lessons.
Requirement:
- 50 Skill
Wednesday
Olivia Swimming Practice
Time: 10:00
Take Olivia to practice.
Victoria Chore Event
Visit the upstairs hallway between Olivia’s room and the MC’s room.
Click on Victoria.
Sleepover #2
Time: 22:00–01:00
Go to bed.
Olivia visits during the night.
Thursday
Madeline Board Meeting
Time: 14:00
Attend the meeting.
Victoria Boxing Training
Time: 20:00
Help Victoria train again.
Friday
Victoria Chore Event
Time: 14:00
Go to your room and click on Victoria.
Dinner with the Girls
Time: 18:00
Join dinner.
Annabelle Art Class
Time: 19:00
Take Annabelle to class.
Sunday
Olivia Swimming Contest
Time: 10:00
Pick Olivia up for the swimming contest.
Requirement:
- 50 Endurance
Victoria Pool Event
Time: 14:00
Talk to Victoria while she sunbathes.
Requirement for front pose:
- 45 Love
Annabelle Workout
Time: 16:00
Help Annabelle train.
H*ntai Impact Meeting #4
Time: 19:00
Meet Annabelle online again.
TV Event #3
Time: 21:00
Watch television with Olivia.
Monday
Victoria Photo Shoot
Time: 19:00
Visit Victoria in her room.
Sleepover #3
Time: 22:00–01:00
Go to sleep.
Olivia visits your room during the night.
Tuesday
Buy Maid Uniform
Visit Dark D*sires at the mall.
Purchase:
- Maid Uniform
Cost:
- $1,000
Madeline Board Meeting
Time: 14:00
Attend the meeting.
Victoria Boxing Event
Time: 20:00
Help Victoria train.
Choose:
- Show her who’s boss
Madeline Late-Night Visit
Time: 23:00
Visit Madeline before bed.
B*ackmailer Message
Return to your room.
You will receive another text from the b*ackmailer.
Sneak into Madeline’s Room
Time: 00:00
Enter Madeline’s room after midnight.
Wednesday
Victoria Maid Uniform Event
Time: 14:00
Go to the Study.
Annabelle Modeling Session
Time: 14:00
Visit the arboretum and help with her modeling assignment.
Annabelle Workout
Time: 16:00
Help her train.
H*ntai Impact Meeting #5
Time: 19:00
Meet Annabelle online.
Sleepover #4
Time: 22:00–01:00
Go to bed.
Olivia visits again during the night.
Thursday
Madeline Board Meeting
Time: 14:00
Attend the meeting.
Victoria Sparring Match
Time: 20:00
Help Victoria train.
Choose:
- Let her win
Friday
Victoria Pool Event
Time: 14:00
Meet Victoria at the pool.
S*y on Victoria
Use the hidden corridor and observe her.
Annabelle Art Class
Time: 19:00
Take Annabelle to class.
Saturday
Scrubble Event
Time: 13:00–18:00
Go to the dining room.
Choose:
- F*ck it!
Requirement:
- 80 L*st
Sunday
Olivia Spa Event
Time: 10:00
Pick Olivia up and take her to the spa.
Wine with Madeline
Time: 21:00
Join Madeline at the pool.
Choose:
- Compliment her legs
Monday
Olivia Conversation Route
Time: 10:00
Visit Olivia.
Ask about:
- Herself
Annabelle Painting Route
Time: 14:00
Return to the arboretum.
Help with the painting assignment again.
Friday
Annabelle Art Class
Time: 19:00
Take Annabelle to class.
B*ackmailer Progression
Go to sleep.
Another b*ackmailer message arrives during the night.
Saturday
Movie Night
Time: 19:00
Join the girls in the living room.
Choose:
- Oh we’re not done yet!
Requirement:
- 80 L*st
Sunday
Dinner Event
Time: 18:00
Join the girls for dinner.
Note: This event cannot be completed on Saturday.
S*y on Olivia
Time: 19:00
Use the hidden corridor.
D*scipline Room Introduction
Time: 00:00
Go to the d*scipline room in the basement.
The room is located beside the washing machines.
Click Madeline’s icon and call her into the room.
Monday
Buy Black Leather L*ngerie for Victoria
Visit Silk S*duction at the mall.
Purchase:
- Black Leather L*ngerie
Cost:
- $1,050
Annabelle Conversation
Time: 11:00
Go to the kitchen and talk to Annabelle.
Discuss:
- MC
- Annabelle
Dinner with the Girls
Time: 18:00
Join Olivia and the others for dinner.
Victoria L*ngerie Event
Time: 19:00
Visit Victoria’s room.
Open your inventory, select the Black Leather L*ngerie, and then click on Victoria.
Madeline Bedroom Conversation
Time: 23:00
Visit Madeline before she goes to sleep.
Olivia D*scipline Room Event
Time: 00:00
Go to the D*scipline Room in the basement.
Click Olivia’s icon and call her into the room.
Tuesday
Buy Pink L*ngerie for Olivia
Visit Silk S*duction.
Purchase:
- Pink L*ngerie
Cost:
- $675
Buy Red L*ngerie for Annabelle
Visit Silk S*duction.
Purchase:
- Red L*ngerie
Cost:
- $825
Madeline Board Meeting
Time: 14:00
Attend the meeting.
Dinner with the Girls
Time: 18:00
Join dinner.
Olivia L*ngerie Event
Time: 19:00
Go to Olivia’s door and give her the Pink L*ngerie.
Annabelle L*ngerie Event
Time: 20:00
Go to Annabelle’s door.
Give her the Red L*ngerie.
Choose:
- Of course!
Victoria D*scipline Room Event
Time: 00:00
Go to the D*scipline Room.
Call Victoria inside.
Wednesday
Dinner with the Girls
Time: 18:00
Join the group for dinner.
Madeline Relationship Event
Time: 21:00
Meet Madeline at the pool.
Discuss:
- Olivia
- Annabelle
- Victoria
Annabelle D*scipline Room Event
Time: 00:00
Go to the D*scipline Room.
Call Annabelle inside.
Thursday
Buy Micro B*kini for Annabelle
Visit Beach Please.
Purchase:
- Micro B*kini
Cost:
- $525
Buy Blue L*ngerie for Madeline
Visit Silk S*duction.
Purchase:
- Blue L*ngerie
Cost:
- $1,250
Give Annabelle the B*kini
Time: 13:00
Visit the pool.
Select the Micro B*kini from your inventory and click on Annabelle.
Madeline Board Meeting
Time: 14:00
Attend the meeting.
Give Madeline the L*ngerie
Time: 23:00
Visit Madeline while she is reading.
Give her the Blue L*ngerie.
Check on Madeline
Time: 00:00
Return to Madeline’s room after midnight.
Friday
Buy Sling B*kini for Madeline
Visit Beach Please.
Purchase:
- Sling B*kini
Cost:
- $875
Annabelle Conversation
Time: 11:00
Go to the kitchen.
Discuss:
- H*ntai Impact
Final Annabelle Workout
Time: 16:00
Help Annabelle exercise.
Give Madeline the Sling B*kini
Time: 23:00
Visit Madeline’s room.
Give her the Sling B*kini.
Madeline D*scipline Room Event
Time: 00:00
Go to the D*scipline Room.
Call Madeline inside.
Saturday
Pool Group Event
Time: 08:00–12:00
Visit the pool and interact with the girls.
Choose:
- Sure, why not?
- Let’s find out
Then select:
- Hell yeah!
Requirement:
- 80 L*st
Scrubble Event
Time: 13:00–18:00
Join the girls in the dining room.
Movie Night Event
Time: 19:00–23:00
Join the girls in the living room.
Olivia Night Visit
Go to sleep.
A nighttime Olivia scene will occur.
Sunday
Olivia Night Visit Continuation
Go to sleep again.
Early Morning Olivia Event
Time: 07:00
Visit Olivia’s room.
Saturday (Next Progression)
Pool Event with the Girls
Time: 08:00–12:00
Return to the pool.
Choose:
- Yes. We are only just getting started
Requirement:
- 80 L*st
Madeline Night Visit
Time: 00:00
Visit Madeline’s room.
Sunday
Arboretum Event
Time: 13:00–18:00
Visit Madeline while she tends to her plants in the arboretum.
Saturday (Final Route Progression)
Pool Event
Time: 08:00–12:00
Visit the pool and interact with the girls again.
Buy B*tt Plug
Visit Dark D*sires.
Purchase:
- B*tt Plug
Cost:
- $675
Victoria Midnight Event
Time: 00:00
Go to your room.
Sunday
Buy Annabelle’s Outfit
Visit Dark D*sires between 08:00–18:00.
Purchase the outfit required for Annabelle’s route.
Final H*ntai Impact Event
Time: 19:00
Use the laptop.
Requirements:
- 10 Gold Coins
Select the dialogue options exactly as follows:
- False
- True
- True
Monday
Victoria Sparring Session
Time: 20:00
Visit the basement gym and spar with Victoria.
Give Madeline the B*tt Plug
Time: 23:00
Visit Madeline while she is reading.
Give her the B*tt Plug.
Wednesday
Shower Event
Time: 14:00–15:00
Visit the upstairs bathroom.
Important: This event cannot be completed on Saturdays.
Sunday
Final Arboretum Event
Time: 13:00–18:00
Visit Madeline while she is gardening in the arboretum.
Choose:
- F*ck her a*s