I think it depends on who you are close with. I got Vynn and Az'Lean. I'm very close with Vynn and somewhat close with Az'Lean and never talk with the others beyond necessary, I assume that's why.
I'm guessing you'd have to choose to hang out with Lester during one of the moments you're given an option to if you want to get enough points with him. As for getting the others, I'm just nice to everyone. Some might say I'm too nice (and in fact Az'Lean did say I'm too nice when setting up the barriers).