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My two favourite people

Summary:

Homestar accidentally ends up dating two of the Strong brothers at the same time without them knowing about the other and has to juggling going to two dates at the same time. Antics ensue.

Notes:

Yeah this is based on the classic "two dates to the prom" sitcom scenario, except theres no prom lol. Yeah i MIGHT have stolen the title from an adventure time episode (thats plot is NOTHING like this fanfic) just because i thought the wording was fitting.

Also parts of this might get rewritten/edited more later on.

Chapter Text

The Homestar Runner was well known for being stupid. He was also well known for loving literally anything and anyone. He fell fast and fell hard quite often.

It was by pure chance that he'd ended up with two boyfriends. His inability to say no and his overwhelming love had caused it. He didn't mean to secretly date two of the Strong brothers at the same time.

Homestar couldn't just pick one. He had too much love in his heart for just one boyfriend! He loved both Strong Bad and Strong Sad but in different ways.

He admired Strong Bad’s confidence and the way he’d do whatever he wanted, whenever he wanted. Also the way he’d walk around half naked, not caring about what the world thought.

At the same time he loved how Strong Sad expressed his feelings, how he'd actually show his love for Homestar by writing him poems and letters, even if Homestar could barely read them due to Strong Sad’s cursive handwriting and the long words he’d used.

Homestar couldn't imagine not being with both of them. They both gave him something different, he needed them both. Even though he had to keep it a secret from both of them.

If Strong Bad found out that Homestar was also dating Strong Sad he’d freak and probably kill his brother in a fit of rage. Meanwhile if Strong Sad found out that Homestar was also dating Strong Bad, he’d probably spiral deeper into his depression, the fact that he alone couldn't satisfy his boyfriend to the point where Homestar would go to his brother would break him.

It was going to happen eventually, whether Homestar wanted it to or not. For now he’d have to keep this stunt going for as long as possible.


As for today, Homestar was looking forward to his planned date with Strong Sad at Marshmallow's Last Stand.

Homestar picked up his hat, placing it on his head. He was excited for today, he was going to his favourite restaurant with one of his favourite people.

Just as he was about to leave, Homestars phone suddenly started ringing. He picked it up, looking at the number, smiling widely when he realised who it was.

“Hi!!” Homestar said, putting it up against his head.

“Hey stupid, wanna go out?” Strong Bad asked nonchalantly.

“Sure!” Homestar replied without thinking.

“Alright. See you at the stick in like an hour. Bye.” Strong Bad stated, because in his mind, Homestar had nothing better to do than ‘hang out’ with him.

“Bye! Love you!” Homestar said back, not noticing that Strong Bad had already hung up.

It was then that Homestar realised what he had done. He already had a date with Strong Sad planned and he definitely didn't want to miss that, but he had also just promised to, ahem, hang out with Strong Bad.

Homestar decided that he’d just have to balance them, go to both dates at the same time.

He couldn't exactly multiply like a bacteria so he'd have to run back and forth. Not that that was a problem, he loved running! After all, he was the Homestar Runner !

He exited his house and began his run to the restaurant and before he knew it, he was already there.

Homestar entered the establishment, looking around at the tables for Strong Sad. Soon he saw him sitting alone at a booth, frantically writing something in a small notepad.

“Hi Strong Sad!” Homestar excitedly said as he approached the table.

“Hey Homestar.” Strong Sad replied, slight enthusiasm in his tone, looking up at the runner as he cracked a small smile. He put the notepad away.

Homestar sat down at the opposite side of the booth.

“Thanks for coming, I wasn't sure you'd show up.” Strong Sad said, relieved for whatever reason.

“Why wouldn't I?” Homestar asked, tapping his feet gently on the floor.

“Well it's just that you're late and the waiter wanted to kick me out for loitering.” Strong Sad leaned his head on his hand.

“Oh I’m sorry” Homestar apologised in what for him was a genuine tone.

Homestar picked up the menu, flicking through the pages, wondering what he wanted. He knew the whole thing, every item on it, back to front, front to back, but he still felt compelled to see his options.

Strong Sad did the same, though he spent more time looking at the items, reading their names and ingredients, instead of just looking at the pictures like Homestar was doing. It wasn't Strong Sad’s first choice of eating establishment, but he didn’t really go out much and his boyfriend seemed to like this place well enough to bring him there so it was probably not bad.

Homestar looked at the clock on the wall. Somehow it was already time for him to see Strong Bad!

“I gotta pee.” Homestar announced, getting up.

“But we haven't even ordered.” Strong Sad retorted.

“Ooooo I want fries.” Homestar said. “I’ll be right back.” He continued on his way, leaving out the front door instead of going to the bathroom door.


Homestar, knowing he was already late, ran as fast as he could across the green landscape of Free Country.

Finally he arrived at the stick, his feet scraping the grass up as he came to a halt. Strong Bad was already waiting for him there.

“Hey where’ve you been? I've been waiting here for like 10 minutes.” Strong Bad was quite annoyed. For the first time ever he was actually peeved that he had to spend less time with Homestar.

“Sorry babe.” Homestar apologised.

“Ew. Never call me that again.” Strong Bad said, slight disgust in his voice. He didn't care about being called pet names, but some of them were just too cheesy, even for him and Homestar.

“So what are we gonna do today?” Homestar asked moving closing to Strong Bad “Are we gonna make out under the bridge?” He quieter said, doing that weird butt shake he did when he was trying to emphasise something.

“I umm… No… We're not.” Strong Bad responded, looking around nervously, despite no one being around.

Strong Bad started walking in a direction and Homestar followed like a lost puppy. Homestar’s curiosity overwhelmed him as he wondered what his boyfriend had planned for the day. It could be practically anything!

Soon they reached the brothers’ Strong house, a place Homestar knew very well. After all, he’d spend most of his time there, it was more of a home to him than his actual house.

“So why’d you make me go to the stick if you wanted to take me here?” Homestar asked as Strong Bad opened the front door.

“I didn’t want Count Dumpula to see us and start writing his weird, homoerotic fanfictions again. Those things give me the jibblies.” Strong Bad shivered slightly, something about the way his brother had portrayed him in those stories disturbed him.

 Strong Bad continued “He said that he’s going on some kind of date. Poor girl… or guy… yeah no, guy. He’s definitely with some guy.” Homestar nervously laughed at the comment.

Entering the house, it was as normal and boring as it ever was. Strong Bad led the way, taking homestar down into the basement, before taking his place on the couch. Homestar followed, sitting on the opposite end.

“Sooooo…” Homestar shifted closer to where Strong Bad was sitting.

“What?”

“What do you wanna do?” Homestar said, leaning closer to Strong Bad. Their faces almost touched, being just a few inches apart.

Suddenly, right at that moment, Homestar remembered that Strong Sad was probably still waiting for me.

Homestar stood up. “I uhh.. I left my oven on. I gotta go turn it off. I’ll be back soon! Love you!” He exclaimed, running out of the room.

“Homestar, wait!” Strong Bad yelled out to no avail.


Homestar panted as he sat down in the booth. To his surprise their food had already come.

“Sorry about that. Y’know, long lines and all.” Homestar apologised.

“It’s fine.” Strong Sad replied, dipping a fry into whatever mystery sauce he had ordered.

“So what’s up with you?” Homestar asked, as genuine as ever.

“Oh I’ve actually been writing a lot lately, mostly just poems and short horror stories.”

“Oooooo… cool!”

“I uh… wrote one for you.” Strong Sad said nervously, shifting through some papers. “Here.” He slid a piece of paper over to Homestar.

Homestar picked it up, slowly looking over it a few times. Even though it was written in cursive and Strong Sad had used quite a few complicated words, Homestar did his best to read it and actually get what Strong Sad was trying to say.

“I love it! Homestar looked up and smiled at Strong Sad. He really did appreciate the effort his boyfriend had put into it, even if he didn’t fully understand the meaning.

“Really?!” Strong Sad asked, a smile creeping on his face. After a few seconds he continued “I really do love you, Homestar.” He blushed, trying to keep eye contact with Homestar.

After a few seconds Homestar replied “I love you too babe”, smiley softly as he did so.

Homestars phone started ringing. He looked at it, just long enough to see that it was ringing before declining the call. Unfortunately, he saw the time on the device. He then suddenly remembered his other boyfriend who he had oh so unceremoniously walked out on.

“I’ll be right back…” Homestar said, once again leaving Strong Sad alone.


Homestar walked back into the basement. Strong Bad was exactly where he had left him, the only difference was that he was now watching tv.

“So how was your oven?” Strong Bad asked, his gaze not moving as he seemingly had sensed Homestar entering, rather than seen him.

“Huh?”

“The oven you forgot to turn off?” Strong Bad continued.

“What?” Homestar had genuinely forgotten about his lie.

“Nevermind.” Strong Bad dropped the subject. Even if Homestar had lied about why he had suddenly ran out it’s not like it was that important.

Homestar took his place on the couch, snuggling up next to his boyfriend.

They sat in silence for a while, watching whatever crappy romcom was on, though Homestar wasn't exactly watching it and neither was Strong Bad.

“Homestar? I uhh… do you wanna live here with me? Y’know like move in or something.” Strong Bad piped up.

Homestars mind blanked. He wanted to say yes but if he did then Strong Sad and Strong Bad would instantly find out.

“I- umm… I-” Homestar stumbled over his words. He then suddenly stood up before running out of the room.

“Homestar?” Strong Bad said, incredibly confused as to why Homestar had just ran out on him instead of instantly agreeing. The Homestar he knew would've said yes. Something fishy was going on.


Homestar ran and he ran fast. He ran all the way back to his other date, Strong Sad, at the Marshmallow's Last Stand. 

“Sorry.” Homestar sat back down at the table.

Strong Sad took a few seconds before answering “Hey Homestar, I’ve actually been meaning to ask you something.” Strong Sad fidgeted with his hands, nervously, trying to look at Homestars eyes but failing miserably.

“Yeah?” Homestar was intrigued, whatever it was he was sure it would be something really gre-

“Do you wanna come live with me? I know my brothers can be chaotic but I just wanna be closer to you, y’know.” Strong Sad said, looking up at the runner, trying to stay calm.

Homestar was stunned. This was not good. not. good.

“I umm… I gotta go.” Homestar darted out of the restaurant.

“Homestar, wait!” Strong Sad yelled out, getting up from his seat. “I'm sorry!” He apologised for whatever he'd done, however, the runner was already far gone.