Pick all the things he likes and at the start with the coffee cup either put Dean or Dave. Dean gives +1 to dean's affection while Dave is +1 to everyone. I think one of the times when Tyson leaves the room from arguing with roswell you can talk to dean about his family or how to ask someon out, I think... It's been a while since i've done deans route. That gives another +1 to dean too.