Either Jack Skelington with no face, of a Slenderman.

the 12 diary hold in business attire attends is over dressed for his dinner date

Huh. Looks a bit like Conan O Brian cept with brown hair

two people sitting on couches chilling looking at the moon reflect on the lake in front of them like its no big deal.

A guy with a red shirt and another guy with a black t-shirt, they are both sitting on benches in the park at night.

Person 1 asks person 2 with red top, called brah what might be up

"brah" has got bad debt, but doesn't seem ashamed about it, or even worried

Guido buying drugs or tanning session

A guide responds to a man, "Drugs? Nah, bro. Gym. Tan. Laundry." each period in the sentence looks like an "o".

some chick looking up at thought bubble of people talking, she has no idea what is going on