For olivia, you have to pick all of the good / romance options for ren and then when you reach the end of your date with ren on day two, instead of going back to his place, choose to go back to yours and you should get it(at least i think that is how I got it)
How to kill Olivia: On Day 2, wait for Ren, then go to your apartment. How to kill Teo: On Day 4, go into the closet with him, then encourage Ren's dark behaviour.