To get this achievement:

- You must confirm all of Emily's beliefs, tell her that you do not drink, you're a virgin, and that you do not want a family after college.

- You must tell all of these things to Evelyn as well, so basically oppose all of Evelyn's beliefs, make sure not to lie. If you lie at all, you won't be able to get the achievement.

- In the argument during Chapter 3, choose Emily. Ultimately, you don't have to talk to Evelyn at all and you can just ignore her. She will get angry and sign off, but after that Emily will talk to you without a time limit so things will be much less stressful. Make sure to tell Emily to tell Jeff that life goes on after a break up, and that she needs to tell Jeff that they are broken up.

-In Chapter 5, Click On matatat's profile and click the the link.

Mission accomplished.