Here is the full list of all 24 We should talk. achievements.
Received all trophies.
Befriend a lonely stranger.
Reach all endings.
Reach ending 8.
Reach ending 6.
Reach ending 5.
Reach ending 3.
Reach 5 endings.
Reach ending 2.
Talk to Sam about your future plans.
Learn about Sam's ex.
Reach ending 4.
Talk to Sam about cleaning the apartment.
Reach ending 7.
Reach ending 1.
Have a steamy conversation with Sam.
Get flirty with Steph.
Reach your first ending.
Reach ending 9.
Talk to Sam about her insecurities.
Learn about Sam's dad.
Lie to Sam about meeting with an ex.
Talk to Sam about going to the gym.
Begin your first playthrough.