apparently its easy
1st meeting
- interact with him
2nd meeting (library at 6:00 pm)
- "ask"
- click the first option above the "thats just how life is"
3rd meeting
- "it was an utter mess"
- click the other option, dont click the "it was very entertaining and informative" one.
4th meeting (library, 6:00 pm again)
- "you can save money either way"
5th meeting (saturday on cafe)
- it should say that the ending failed, meaning you got the bad ending.