Will you go out with me?

Do you have any suggestions?

I know a good place for lunch! 

At the Diner: 

You're really pretty. 

(Any choice of food works here) 

It just sounded good, okay? 

(Don't talk about anything, jump straight to Finish Date for speedy rejection)

Nevermind, I'm going home, bye.

This coffee shop, right here.

Boobs.

Try to scare Mona.

At the Haunted House or Shopping District:

Succeed the first date, but fumble getting invited to the party. 

At the Haunted House: 

Any choice works here. 

Just act normal. 

At the Spooky Shopping District: 

Just Finish Shopping without doing anything. Easy!

Will you go out with me?

I know a good place for lunch!

At the Diner:
You seem like an interesting person.

I just thought I'd try something new, y'know.

Talk about hobbies + employment + cats.

Haunted House or Spooky Shopping District (order does not matter)

At the Haunted House:
(Any choice works here, personally I think screaming is funniest)

Just act normal.

At the Spooky Shopping District, Gaming Store:
What dice set are you going to get? OR Observe the plush creatures nearby instead.

At the Spooky Shopping District, Costume Store:
(Buy any costume. If you want to follow the "canon", Phoenix Saulman)

At the Party:
Continue to be in awe of Mona's majesty OR QUICKSAVE QUICKSAVE QUICKSAVE Q-

(optional, but fun) Wait, hold on, I'm not ready!!.

Mona, would you be my girlfriend!?

At the Cafe:
Will you go out with me?

I know a good place for lunch!

At the Diner:
You seem like an interesting person.

I just thought I'd try something new, y'know.

Talk about hobbies + employment + cats.

Haunted House or Spooky Shopping District (order does not matter)

At the Haunted House:
(Any choice works here, personally I think screaming is funniest)

Latch onto Mona's arm.

At the Spooky Shopping District, Gaming Store:
Do you play D&D, Mona?

At the Spooky Shopping District, Costume Store:
(Buy any costume. I like the strange king's costume most, for extra flavor text.)

At the Party:
It's so pretty, I love it! OR You must have spent a long time on it, the costume is so well-made!
Mona, would you be my girlfriend!?

At the Shopping District:

Follow the Demon GF guide until you're at the shopping district. Finish Date without buying a costume.