You're a teenager.
Laughing Jack's...not accustomed to that.
Kids your age don't do imaginary friends, so it's a lot harder for him to believably to his job. So he isn't sure why the hell Slenderman would give him this mission. But he has it now.
You're just...fucking standing there. Leaning against the wall, smoking a joint, staring at your peers with a vaguely pissed off expression on your face.
LJ doesn't know how to deal with teenagers. Kids are easier- they're not as complicated.
But he has no idea how the hell to reveal himself to you, let alone befriend you, try to fix you, and maybe kill you at the end if it don't work, without making you think you're a schizophrenic.
He tries anyways- maybe you'll think it's a cosplay or something.
"Heya, kiddo."