Erica (Second Playthrough - Backstabber, Not Alone)
The trophies in this run give a little bit more leeway, but our decisions are still pretty heavily influenced by collectibles. Backstabber is pretty much the opposite of Failure to Comply as you want to gain Blake's trust.
Backstabber:
9:05 (Give him the book)
13:00 (Go Straight Outside)
27:00 (Accept Therapy)
46:43 (It may be better to stay put, but you can follow him and warn him about the intruder which will help with the voyeur collectibles)
56:30 (Give helpful information and accept Blake's orders)
1:03:43 (Worry, Berate and I'm Going Crazy are the alleged keywords to trigger the opportunity to kiss Blake. Then lie to him about knowing where to find Mia)
1:15:50 (You must accept to go with Mia)
1:23:10 (You must kill the guard or you will not have the knife)
1:25:00 (Attack Blake)
Subliminal: 1:10:25
You have to lie to Blake about knowing where to find Mia to access this.
Fall Out Girl:
22:07 (Walk on Carpet)
34:32 (Defy Toby)
3/3 Trophy should unlock after credits
Voyeur:
46:55 (Follow Blake and look in the hole behind the picture twice)
54:10 (This comes along with spending the day with Kirstie)
1:06:30 (This comes with kissing Blake for the Backstabber trophy)
8/11 locations total
Paperwork:
1:00:00 (This will also get you the Proud Father trophy and comes naturally with hanging out with Kirstie)
7/10 Documents total
Botanist:
28:55 (Accept therapy, oleander flowers will be one of the slides)
40:15 (Dump the perfume in the trashcan. You can also get this in another path by hanging out with Tobi)
Total 6/7 Oleander locations
Backstage Pass:
53:17 (Hang out with Kirstie and she will show you one of the locations)
4/5 Epsilon Locks