first off I just wanna say how cool you set up your request blog, I made mine a while ago and I'm still trying to figure out how I want it to look. Definitely jealous lol!
Anyway, could you do some Jack O' relationship headcannons please?
General HCS of Jack-O in a relationship!
No doubt about it is that she would often play pranks and often tease you about stuff. She loves seeing you smile or just getting a rise out of you for fun. She loves to just have a nice time with you whenever she is in a more upbeat and happy mood.
However, when she is in a more serious and level-headed attitude, she often just likes to do something relaxing like watch a movie with you on the couch as a way to spend quality time with you. She would also have meaningful conversations with you and be honest with you as you both talk about your emotions.
She absolutely loves physical affection. Anything you give her, she would love. Hugs and hand holding are a personal favorite of hers and she'll randomly just hold your hand because she felt like it. She adores hugs and will gladly take them and give you a bone crushing hug in return.
You better hope you like Halloween because for the entire month of October, she will ask if you guys can go on Halloween themed dates with the most puppy eyes imagineable. She thinks it's really romantic to go on trick-or-treating with her on day or Halloween and considers it a date rather than just celebrating the holiday as a whole.