Just responded for 2nd bad ending, but for #1 out of the first 2 bad endings, just be mean, hyper-aware/inquisitive, and CLOCK HIS TEA ALOT! T_T Focus mainly on “Confirming his car troubles”, Observing him, and playing with the radio. Don’t ask about his family or pry too much about his college life. Just create an overall negative tone/atmosphere with him and you will get that specific ending.