In order to obtain all the achievements, only one playthrough is needed, but you will have to save / reload at specific points (or use mouse wheel up to go back to the choice and pick a different option). These are mentioned in this guide.
No
🏆 Greetings!
Go back to sleep
Can’t sleep
🏆 A: Caffeinated
[Any]
[Any]
East Coat Night Time
💾 SAVE POINT 1 (at the choice: Ask mom / Ask Dad)
Ask mom about stars
🏆 A: Mom’s best!
🔄 RELOAD SAVE POINT 1
Ask Dad
🏆 A: Daddy’s favorite!
East Coast
[Any] (but maybe “Give a moment” is better)
Leisure Park, East Coast
[Any]
💾SAVE POINT 2 (at the choice: Curious / Concerned)
Curious
🏆 The Morning Hours: 7
🔄RELOAD SAVE POINT 2
Concerned
🏆 The Cow: 83
Turlene Highway
Take a look
💾SAVE POINT 3 (at the choice: Play with toy / Change radio)
Play with toy
🏆 Unicorn!
🔄 RELOAD SAVE POINT 3
Change radio
🏆 Vibing
💾SAVE POINT 4 (at the choice: Uncertain / Friendly)
Uncertain
🏆 The Cow: 42
🔄RELOAD SAVE POINT 4
Friendly
🏆 The Sincerity: 4
Icecream cart
[Any]
[Any]
💾SAVE POINT 5 (at the choice: Walk away / Pay)
Walk away
🏆 The Opener: 6
🔄RELOAD SAVE POINT 5
Pay
🏆 Originator: 5
Eating icecream
[Any] (first option is nicer)
Home
[Any]
[Any]
Ignore
🏆 عَنْ عَبْدِ اللهِ بْنِ عَمْرِو عَنِ النَّبِيِّ صلى الله عليه وسلم قَالَ إِنَّ رُوحَ الْمُؤْمِنَيْنِ لَيَلْتَقِيَانِ فِي مَسِيرَةِ يَوْمٍ وَمَا رَأَى أَحَدُهُمَا صَاحِبَهُ 261 الأدب المفرد للبخاري
[Any]
Salina’s hospital
[Any]
💾SAVE POINT 6 (at the choice: Tell her / Keep it a secret)
Tell her
🏆 Ta-Ha: 26
🔄RELOAD SAVE POINT 6
Keep it a secret
🏆 The Relief: 2
Present Day
💾SAVE POINT 7 (at the choice: Accept Fate / Ignore Fate)
Accept Fate
🏆 The Spoils of War: 70
🔄RELOAD SAVE POINT 7
Ignore Fate
🏆 Luqman: 17
Watch the credits until the end (songs list)
Click on the two people (or in the area around them for a bit)
🏆 You are so sweet-!