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 (Ted) endings in one play-through you have to choose these choices:
(The way you talk is cute)
(He should have worked it out first)
(Country)
(I like the color of it)
(Ask Jeff about your idea)
(Agree with him)
(Ask about his father)
(Why don't we fundraise)
(Coffee)
(I only want to dance with you)
(I don't blame 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
Hope this helps!