We're going to do a time skip to where you two already became a couple.
Slenderman
I feel like he would take you on a dinner date maybe old fashion but I think that's how he wants it.
Jeff the Killer
Obviously you guys don't go to parties. Instead you two something quite and simple.
Ben Drown
Does play video games count? Well if going to a arcade is gaming date.
Eyeless Jack
Of course it wouldn't be anything food related. You 2 hang out at Jack's old college when no one's around.
Ticci Toby
You guys go to ihop for a breakfast date. He'd ordered waffles and you'd get pancakes.
Masky
If he wants cheesecake, then the two of you would go to a cafe.
Hoodie
You guys go to the park and go on the swing.
Laughing Jack
Jack would take you to his carnival and the two of you would do everything together.
Homicidal Liu
Liu sometimes takes you to the movies
Bloody Painter
You go to the art museum to see the wonderful art works
The Puppeteer
You guys would go to the theatre
Jason the ToyMaker
Your date would be very romantic. Dinner, dancing, and watching the stars.
Nathen the Nobody
I feel like you 2 would take a walk down the beach together.
DollMaker
Maybe you guys go to build a bears and make each other bears.
Dr. Smiley
For your guys' date, Dr. Smiley would give you a relaxing massage because he feels like any other dates would make you stress out.
Dark Link
He would take you to his world
Glitchy Red
You 2 play Pokémon GO together
Lost Silver
You 2 just relax at home and watch Netflix
Hobo Heart
You guys go to the forest and have a picnic
Chess Master
Does playing chess counts as a date?
X-Virus
You two go to the science center