This is an edited log of the playthrough I managed to unlock the achievement on. Some of the classes can be swapped occasionally since there are a few pointless ones (especially towards the end), due to reloading saves to pass ability checks or having nothing else to do. If you are only after the Keep Your Friends Close achievement, you can safely quit after week 28 (since it will unlock then).

The achievements that are included in this guide should be Keep Your Friends Close, A Dangerous Juggler, Illuminate!, Off With Their Heads, Rebellious Province, Long Live The Queen. If I've missed any or one of these doesn't unlock after the playthrough, let me know.

Changing outfits is crucial, since some checks will not be met without the proper outfit.

(Classes in parentheses.)
Weekend actions in bold.
Player choices are underlined.
(Outfit changes underlined in parentheses.)
Unlocked actions/outfits in italics.

Week 1

(Studied Foreign Affairs in the morning.)
(Studied Foreign Affairs in the afternoon.)
Sneak Out

Week 2

(Studied Accounting in the morning.)
(Studied Accounting in the afternoon.)
Player chose: Send her away
Sneak Out

Week 3

(Studied Accounting in the morning.)
(Studied Accounting in the afternoon.)
Attend Service

Week 4

(Studied Ciphering in the morning.)
(Studied Ciphering in the afternoon.)
Attend Court

Week 5

(Studied Trade in the morning.)
(Studied Trade in the afternoon.)
Attend Court

Week 6

(Studied Production in the morning.)
(Studied Production in the afternoon.)
You have unlocked a new outfit!
Player chose: I will do it
Play with toys

Week 7

(Studied Dance in the morning.)
(Studied Dance in the afternoon.)
Player chose: Punish her
Visit Dungeons

Week 8

(Studied Flexibility in the morning.)
(Studied Flexibility in the afternoon.)
Player chose: Invest
Sneak Out

Week 9

(Studied Reflexes in the morning.)
(Studied Reflexes in the afternoon.)
You have unlocked a new outfit! You may now play Sports on the weekends.
Talk to your father

Week 10

(Studied Dance in the morning.)
You may now attend Ballroom Dancing on the weekends.
(Studied Flexibility in the afternoon.)
Player chose: Offer to punish the Duchess of Hellas
Player chose: Execute her
Visit Selene

Week 11

(Studied Reflexes in the morning.)
(Studied Reflexes in the afternoon.)
Sneak Out

Week 12

(Studied Polearms in the morning.)
(Studied Polearms in the afternoon.)
Player chose: Politely decline
Sneak Out

Week 13

(Studied Polearms in the morning.)
(Studied Internal Affairs in the afternoon.)
Player chose: Put her to work
Sneak Out

Week 14

(Studied Foreign Intelligence in the morning.)
(Studied Foreign Intelligence in the afternoon.)
Sneak Out

Week 15

(Studied Ciphering in the morning.)
(Studied Foreign Intelligence in the afternoon.)
Player chose: Religious doctrine
Sneak Out

Week 16

(Studied Internal Affairs in the morning.)
You have unlocked a new outfit!
(Studied Internal Affairs in the afternoon.)
Player chose: I will parade and make a speech
Player chose: Fight him
Attend Service
(Put on the intrigue outfit.)

Week 17

(Studied Ciphering in the morning.)
(Studied Instrument in the afternoon.)
Player chose: Someone scandalous
Player chose: Accuse him of sending assassins
Player chose: Execute him
Sneak Out

Week 18

(Studied Public Speaking in the morning.)
(Studied Public Speaking in the afternoon.)
Player chose: Shame her with silent scorn
Player chose: Noble plots
Visit Selene
Player chose: Let Selene have her way

Week 19

(Studied Voice in the morning.)
(Studied Voice in the afternoon.)
Player chose: Keep them the same
Visit Selene

Week 20

(Studied Instrument in the morning.)
(Studied Archery in the afternoon.)
Player chose: Execute him
Walk in the gardens

Week 21

(Studied Court Manners in the morning.)
(Studied Court Manners in the afternoon.)
Play with toys

Week 22

(Studied Flattery in the morning.)
(Studied Flattery in the afternoon.)
Player chose: Leave him with Arisse
Walk in the gardens

Week 23

(Studied Court Manners in the morning.)
(Studied Flattery in the afternoon.)
Player chose: Test her for secret skills
Talk to Sabine

Week 24

(Studied Public Speaking in the morning.)
You have unlocked a new outfit!
(Studied Public Speaking in the afternoon.)
Player chose: Send the musician to gather more information
Walk in the gardens.
(Put on the conversation outfit.)

Week 25

(Studied Public Speaking in the morning.)
(Studied Public Speaking in the afternoon.)
You have nothing more to learn about Public Speaking.
Player chose: Try to win her support
Sneak out.

Week 26

(Studied Reflexes in the morning.)
You have nothing more to learn about Reflexes.
(Studied Public Speaking in the afternoon.)
You have nothing more to learn about Public Speaking.
Player chose: Send emergency aid
Sneak out.

Week 27

(Studied Wield Magic in the morning.)
(Studied Wield Magic in the afternoon.)
Player chose: Go to Sudbury for Gwenelle's party
Sneak out.

Week 28

(Studied Sense Magic in the morning.)
(Studied Sense Magic in the afternoon.)
Player chose: Agree to marry him (Achievement : Keep Your Friends Close)
Sneak out.

Week 29

(Studied Resist Magic in the morning.)
(Studied Resist Magic in the afternoon.)
You have unlocked a new outfit!
Sneak out.

Week 30

(Studied Sense Magic in the morning.)
(Studied Resist Magic in the afternoon.)
Sneak out

Week 31

(Studied Wield Magic in the morning.)
(Studied Wield Magic in the afternoon.)
Sneak out
(Put on the economics outfit.)

Week 32

(Studied Sense Magic in the morning.)
(Studied Resist Magic in the afternoon.)
Player chose: Employment
Player chose: Save it for later
Sneak out
(Put on the lumen outfit.)

Week 33

(Studied Sense Magic in the morning.)
You have nothing more to learn about Sense Magic.
(Studied Resist Magic in the afternoon.)
You have nothing more to learn about Resist Magic.
Player chose: None
Attend Service

Week 34

(Studied Instrument in the morning.)
(Studied Resist Magic in the afternoon.)
You have nothing more to learn about Resist Magic.
Player chose: Recruit soldiers
Player chose: Stay in the capital
Attend Service

Week 35

(Studied Swords in the morning.)
(Studied Swords in the afternoon.)
Attend Service

Week 36

(Studied Foreign Intelligence in the morning.)
(Studied Foreign Intelligence in the afternoon.)
You have nothing more to learn about Foreign Intelligence.
Player chose: Accept his terms
Player chose: Magic sword
Attend Service

Week 37

(Studied Dance in the morning.)
(Studied Flexibility in the afternoon.)
Player chose: Ask about Charlotte's powers
Player chose: Execute the entire family
Attend Service

Week 38

(Studied Dance in the morning.)
(Studied Flexibility in the afternoon.)
Player chose: An extravagant feast
Sneak out

Week 39

(Studied Internal Affairs in the morning.)
(Studied Ciphering in the afternoon.)
You have nothing more to learn about Ciphering.
Sneak out

Week 40

(Studied Internal Affairs in the morning.)
You have nothing more to learn about Internal Affairs.
(Studied Ciphering in the afternoon.)
You have nothing more to learn about Ciphering.

Thank you for reading this guide!

I appreciate the feedback so feel free to comment, especially if you find any errors (I might have missed something while editing the log)!

Also, if you'd like the complete log, let me know.