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Matchmaker with Holly & Friends

Summary:

Working on a summary

Notes:

I would like to address somethings in this:

1. Holly and Derek are kind of friends in this. Like they got that platonic madwheeler type of relationship.

2. Max is awake in this, but she is half-blind and she also doesn't have her full mobility back yet so she uses a cane.

3. The tags will change depending on where I take this story.

4. IM SPEADING SLEEPERBUILD MIKE PROPAGANDA (that should be a tag btw)

Chapter Text

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Holly loves her family.

Well… mostly.

Her dad is chronically lazy, usually parked in his chair like it’s his natural habitat. Her mom sometimes drinks this strange, sharp-smelling juice she insists is “only for adults,” which Holly personally thinks smells like old fruit and bad decisions.

But still. Holly loves them.

Even so… none of them are like Will.

Holly really loves Will.

He’s one of her favorite friends of Mike’s, maybe even her favorite. Will has been part of her life for as long as she can remember. Technically, he’s been part of Mike’s life that long, but Holly considers that close enough. If someone spends enough time in your living room, eats enough of your snacks, and listens patiently while you talk about your drawings, they basically become family.

And Will is awesome.

He can draw really well. Like, the kind of well that makes Holly stare over his shoulder and think maybe drawing is actually magic. He’s nice—nicer than most people Mike hangs out with—and he actually lets her give him makeovers.

Real ones.

Hair clips. Sparkly eyeshadow. Sometimes even nail polish if she can convince him.

Better yet, he sometimes convinces Mike to join too, which Holly considers one of her greatest accomplishments.

It got even better when the Byers moved closer. Now Will was around even more, and Holly felt like she had her own personal artist-slash-playmate whenever Mike and his friends weren’t busy doing whatever it is that nerdy teenage boys do.

So yes.

Holly loves Will.

And in her mind, there has never been a version of the future where Will wasn’t around.

Which is why the conversation at dinner ruined everything.

It had started normally. Spaghetti. Mike complaining. Her dad barely paying attention.

Then her mom asked a simple question.

“What kind of colleges do you boys think you’ll want to go to?”

Mike had shrugged, Will had laughed nervously, and the conversation moved on.

But Holly had frozen.

Because suddenly, something terrible occurred to her.

Will and Mike might go to different colleges.

And if that happened…

Mike wouldn’t bring Will home anymore.

Two hours later, Holly was still sitting on her bed, knees pulled to her chest, staring miserably at the floor.

Her room was quiet except for the soft hum of the hallway light outside.

A gentle knock sounded on her doorframe.

“Holly?”

Her mother stepped into the doorway, her expression soft with concern.

“Honey, are you okay?” Karen asked gently. “You’ve been quiet since dinner.”

Holly didn’t answer. She just stared harder at the floor.

Karen sighed softly and walked into the room. Sitting beside her on the bed, she pulled Holly gently against her chest.

“I don’t want him to go,” Holly mumbled into her sweater.

Karen blinked.

“Huh?”

She leaned back slightly so she could hear her better.

“What was that, sweetie?”

Holly looked up, tears glazing her eyes.

“I said… I don’t want him to go.”

Karen frowned in confusion.

“You don’t want who to go?”

Holly shot to her feet in frustration, throwing her arms into the air.

“Will!” she cried. “Mom, I don’t want Will to leave!”

Karen looked startled.

“If he goes to college somewhere far away,” Holly rushed on, words tumbling out, “then Mike won’t bring him here anymore! And if he doesn’t come here, then I won’t have anyone to draw with or play with, and then I’ll be sad—and Mike will be sad—and—”

“HOLLY.”

Karen’s firm voice cut through the spiral.

Holly stopped mid-rant.

Her mom crouched down so they were eye level.

“Honey,” Karen said gently, “I know you love spending time with Will. But he and Mike are sixteen. Someday they’re going to grow up and have lives of their own.”

She placed a comforting hand on Holly’s shoulder.

“It’s okay to be scared when things change. Everyone feels that way sometimes. But that doesn’t mean you shouldn’t enjoy the time you have with them right now.”

Holly stared at her.

Her mom clearly didn’t understand the real problem.

Mike and Will going to college wasn’t the issue.

Holly was completely fine with that.

The problem was that she had always assumed they would go to the same college. Together. Obviously.

It had never occurred to her that they might go to different ones.

Which completely ruined her long-term plan to convince Will to wear a princess dress.

A very specific princess dress.

The one her mom had in the back of her closet.

Holly had discovered months ago that Will and her mom were the exact same dress size. She’d been slowly working toward convincing him for nearly six months.

Six months!

This college nonsense would destroy everything.

She opened her mouth to explain this extremely important issue—

But her mom kept talking.

“And besides,” Karen said thoughtfully, “the only way for Will to visit as often as you seem to want would be if he married into the family somehow.”

Holly blinked.

“Wait.”

She stepped back slightly, staring at her mother.

“What did you say?”

Karen looked confused.

“Which part, honey?”

“The part about marriage.”

“Oh!” Karen said, waving her hand casually. “Well yes. If Will wanted to visit that often when he’s older, he’d probably have to be in a relationship with someone in the family. Or married to them.”

She shrugged lightly.

“But that’s not very likely. There are only two girls in this family, and you’re much too young. And Nancy is pretty clearly with Jonathan, so—”

Holly’s eyes widened.

An idea exploded into her brain like fireworks.

Before Karen could finish her sentence, Holly bolted out of the room, sprinting down the hallway with a brand-new plan forming rapidly in her head.

Karen slowly stood up, staring at the open doorway her daughter had just disappeared through.

“…And not even a thank you,” she muttered.