Dating PennyWise would include

Him putting a shit load of balloons in your room. So every time you open your door balloons come flooding out.

Privacy is not an option. He appears out of nowhere and knocking on doors is just a concept to him.

Missing children posters strewn about the town. (Obviously)

Him cooking weird things. "Um Penny, is that an eye ball?" You asked. "Oh, no, it's an olive!"

Him being a bad liar.

Him always trying to make you float.

Him doing his crazy clown dance when you're sad. (Obviously)

"Penny, put that kid down! Now!" You commanded. "But-" "No, this is your 3rd kid today!"

You and Penny making morbid jokes together.

Him worried not being real enough for you.

Him throwing surprise parties for you.

POP, POP, POP, POP!

Him randomly jingling his bells from his costume.

Him doing weird ass shit with his eyes all the time just to freak you out or make ya laugh whichever one.

His rabbit teeth.

Him taking longer to put on his makeup than you.

Him smelling like death and decay after feasting.

Him randomly crawling through movie projectors if the movie is boring or he just doesn't like it.

You cleaning the blood off of his lips after he has eaten.

His favorite movie is Silence of the Lambs. (Pretty obvious)

Him loving to play dress up. (I mean he is a shapeshifter. He makes really good impressions of dead celebrities)

When it comes to grocery shopping there is always a pack of balloons in the cart.

Him not liking people calling his house a, "Crack House."

You asking PennyWise if he has a soul or not.

When you visit Penny in the sewers you always say, "This place is a dump." Not realizing that you insulted him.

Always new kids floating in the sewers when you visit him.

Him having a shrine of John Wayne Gacy.

"Penny, do you want an arm or a leg?" You asked. "Both!" He said as his eyes going walleyed.

He's great with kids.

Birthday parties are his favorite.

You not knowing what his eye color is because it's always changing.

He loves it when you wear clothing with ruffles.

Him going on YouTube to look up makeup tutorials. (His favorite brand is Urban Decay.)

He loves going inside refrigerators and coming out of them.

Contorting his body in strange looking positions.

Him drooling excessively.

His drool getting on your clothing. "You really need to control that Penny." You said.

"Did you eat?" You asked. He looked over at you with his yellow, orangey eyes saying nothing.