My Creepypasta/Slenderverse Headcanons [redone]

Failed relationships

Jeffery Woods and Nina Hopkins
Theme song: 'Daddy Issues' - The Neighborhood
Tropes:
- young love
- friends to lovers
- bubbly x slightly annoyed by it
- right person, wrong time
- common interests
Healthy or toxic: healthy
Who fell first: both
Who fell harder: Nina
Pet names:
- Jeff called Nina babe, baby, princess, and sunshine
- Nina called Jeff baby, my prince, lovey, and darling
Confession:
Nina wrote Jeff a love letter.
Fun facts:
- They were together for over a year before Jeff ran away from home.
- They met when they were both 8, when Nina first moved to town. They were friends for years before they started dating at age 12. Nina was one of the only people at school who didn't see Jeff as a freak.
- When they started dating, Liu disapproved because of how protective he was over Jeff. But with some convincing, he "allowed" Jeff and Nina to continue dating.
- While Jeff was an introvert, Nina was an extrovert. Pri often tried convincing her friends to like Jeff, but they kept bullying him. Nina still kept dating him nonetheless and didn't care what their friends thought.
- Jeff often got embarrassed when Nina was extra affectionate with him, but at the end of the day, he just wasn't used to it (of course, Liu was affectionate with him, but Nina was on a whole new level).
- Nina gave Jeff a diary for his 12th birthday. He used it up until he ran away.
- Like pri now does with Painter, Nina liked poking Jeff's cheek and giving him love bites.
- They sometimes gave each other hickies just for fun. Liu was furious when he first found out, but Jeff was quick to assure him that they weren't having sex.
- Ben was basically their third wheel.
- Jeff sometimes tried to pick Nina up, but he usually failed.
- Whenever Jeff got another bruise, Nina would always kiss it.
- Nina sometimes practiced their makeup skills on Jeff. Jeff dreaded it, but he was never forceful about not taking part in it.
- They liked doing karaoke together.
- Jeff secretly loved it when Nina sat in his lap.
- Because they were dating, Jeff always got free drinks at Nina's mom's coffee shop.

Randy and Brittany Winchester
Theme song: 'Washing Machine Heart' - Mitski
Tropes:
- wrong person
- one-sided love
- afraid to commit
- affectionate x hesitant
Healthy or toxic: rocky
Who fell first: Brittany
Who fell harder: Brittany
Pet names:
- Randy called Brittany babe
- Brittany called Randy babe, baby, and handsome
Confession:
Brittany: "I think you're really cute. Wanna go out?"
Randy: ". . . Y'know what? Why not?"
Fun facts:
- They dated for five months when Randy was in his junior year and Brittany was in its freshman year.
- Randy never really loved Brittany - he wanted to, but in the end, he was only using their relationship to try and suppress his feelings for Keith. Truth be told, he found her a little annoying, but he never said it to its face.
- As it often happens with first love, Brittany was convinced that Randy was the one she was going to marry one day. She was also pretty clingy, because it wanted attention after a life of being used and neglected. She even tried pushing Randy away from his friends, none of whom approved of it. She also bullied Keith behind Randy's back because it knew he had a crush on him.
- When Randy and Brittany first started dating, Randy's mother was concerned that Randy was only using Brittany for its money, which Randy swore he wasn't. Likewise, Brittany's mother forbade the relationship because Randy and his family were poor, so Brittany had to keep seeing Randy without its mom's knowledge.
- It didn't take long for Randy to realize that Brittany was very insecure and didn't eat a lot. He tried to help her as best he could, even splitting his school lunches with her sometimes, but it was never really enough.
- Brittany turned 15 while they were dating. To celebrate, Randy took her out and gave her a bunch of candy, but Brittany hardly ate any of it.
- One time, when Brittany had snuck Randy into her mother's house, she asked him to come into its bathroom to talk to her. When Randy entered, he found Brittany completely bare-chested, and he freaked out. He thought she was trying to get sexual with him, but instead, Brittany asked him if he thought its breasts were too small. Randy's response was, "Boobs are boobs no matter the size."
- Brittany often gave Randy expensive gifts. When they broke up, Randy gave back one of them, a watch.
- The night Brittany finally realized that Randy didn't love it, Randy had called her drunk in the early morning and asked her to pick him up. Brittany had her butler Sean Luke drive it to the location, and Randy stumbled out of a club he had snuck into with a fake ID. He kissed her, and for a moment, Brittany was charmed until Randy said, "Thanks for the ride, Keith." Brittany didn't say a word for the rest of the incident and cried itself to sleep when she got home.