For all the endings achievements make sure to choose play the game in visual novel mode the second option and choose the special ending option the second option once again.
In order to get all (Daren) endings in one play-through you have to choose these choices:
(Try to be polite)
(I want to know him better)
(Definitely not what I was expecting)
(It's definitely historical fiction)
(Mint ice cream looks so good right now)
(Show him with Darren)
(That's pretty silly)
(Be Civil)
(After him)
(Suggest to call an attendant to help search)
(Don't help him)
After you finish picking up all these exact choices both achievements for both endings will unlock.
Hope this helps!
Also check this perfect full achievement guide done by Cheevo Guides
