Here is a guide to 100% the game. (Working on expanding the descriptions of certain achievements.)
Distinguished Man of Letters

Balls of Steel

Once upon a time

Supermarket Romance

Then on Day 8, when talking to Riley, select the “You are” option towards the end of the conversation.
Didn’t need to see that

Then on Day 10, in the evening watch ALL of the footage of Brody.
Taking out the trash

Then on Day 11, when at the store with Liza, Punch Brody.
Taming the tsundere

On Day 26, when at the nightclub with Bella, tell Megan you are Bella’s boyfriend and Confirm. Choose the Dance with Bella option. Then in the hotel select Me too when Bella is nervous.
The Great Outdoors

Then on Day 12, when in the park, lick Bella’s p*ssy.
The Secretary

Then on Day 8 go to Discreet Inc and complete the questionnaire, once you leave the achievement is unlocked.
Do eat that yellow snow

Ma Belle

Then on Day 7, offer to help Bella with her problem.
Thank you, come again

A Good Friend

On Day 22, when talking to James, agree to Share Ana with him.
Blonde Angel

Then on Day 5, after the dinner date with Liza, Kiss her on the mouth.
Oedipus Complex

The Redhead

Then on Day 6, when at the cinema with Rachel, choose both “It’s arousing” and “Would you like that?” options. After getting home you will receive the achievement.
Objet d’Art

Then on Day 143, visit Rebeca.
The things we do for love

Then on Day 14, visit Dwayne’s house and at the end of the scene you will receive the achienement.
Feels like home

The Cherry

Can’t touch this

Fallen Angel

Then on Day 37, sleep with Liza.
Studied Hard

Glorious!

From dusk till dawn

Holmes and what son?!

On Day 30, Do not accept Adriana’s termination and Ask for one last session.
Then on Day 31, visit Discreet Inc.
One for the team

Assault on Decency

Then on Day 23, compliment her at the Opera to get her number.
Then on Day 25, Accept Iris offer for coffee. Make a move on her and Go after her upstairs.
Preacher of Love

Then on Day 23, compliment Iris at the Opera to get her number.
Then on Day 25, Accept Iris offer for coffee. Make a move on her and Go after her upstairs. Also Acknowledge her at the end
Sisterly Trust

Then on Day 32, Propose union with Rachel and Bella when talking to both Rachel and Bella.
Then on Day 34, Sleep with Rachel.
With your pants down

Show me the money!

Uncle!

Then on Day 6, she will ask for the money in the morning, after this interaction you will get the achievement.
Hot summer night

Then later in the evening, accept Nia and Rachel’s gift offer.
Hell’s Bells

On Day 24, confront Dwayne with Bella.
Master Baker

Do this 50 times in a single playthrough to receive the achievement.
Lord of the Rings

On Day 142, invite Iris and Riley to come with you to Belugio.
Bad Brother

One swallow does not a summer make

Do this 20 times in a single playthrough to receive the achievement.
Like a virgin

Face/On

Do this 30 times in a single playthrough to receive the achievement.
Body Love

Do this 30 times in a single playthrough to receive the achievement.
Two Soccer Teams

You must not be on the submissive route with Bella.
TBC…
All in the family

Come to mommy

Be in a relationship with Liza to get to Iris, then stop the Liza relationship afterwards.
Only have Rebecca come and say goodbye to you when leaving the island.
TBC…
By TheBoxManer
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