Chat a man up!

To start, I should probably explain the reasoning behind why these two could be considered a canonic couple.

One of Dan Wilson's general gossip quotes is "Apparently Derby and Bif are gay for each other." Now this could be considered nothing more than idle chatter, many of Dan's lines could be interpreted this way, however it is an interesting premise that many have taken to fanon to explore.

At first, I really didn't like the idea of them being together. There are already plenty of canonically bisexual/gay characters, and adding many more would feel too removed from real life.

But the more I thought about it, the more their dynamic evolved in my head. And so I'm now here to explain said dynamic if they were able to be further developed.

𝕋𝕙𝕖 𝔹𝕖𝕘𝕚𝕟𝕟𝕚𝕟𝕘

Derby and Bif met in Bullworth, and it was no where near the 'love at first sight' that some people may assume. The two were fairly indifferent to each other, but as the years at Bullworth pushed on, so too did their relationship.

As Derby ascended to leader, he took Bif in as his second in command - he was loyal, strong, and genuinely liked by the other members of the clique. It was unfortunate that money didn't mean much to him, and he talked in such a middle class accent, but Derby knew he was a powerful asset. And it helped that Bif was able to put up with him more than the other's seemed to.

Bif on the other hand, had started to notice Derby more than usual. He happily followed Derby's every word. The two were aware of this dynamic - Bif would follow Derby, in exchange for his praise.

𝕋𝕙𝕖 𝔹𝕠𝕩𝕖𝕣

Bif grew up with a slightly more tame family, no inbreeding or fancy accents. But from a young age, he did struggle with his grades. He was never reprimanded harshly, however it was still wished that he would do well, so after finding his footing in boxing, he decided that becoming a professional boxer would be a good middle ground between pleasing his family, and doing something he genuinely loved.

Praise is something Bif constantly seeks, but he never wants it for free. He has to earn it - whether that be through boxing, helping out friends, or following Derby's orders.

𝕋𝕙𝕖 𝕃𝕖𝕒𝕕𝕖𝕣

Derby's childhood was a little different. He wasn't just born to money; he was born to power, and he was expected to do everything that was needed for him to succeed that. Every aspect of his life was controlled, and he was never able to learn who he really was. And thanks to this loss of autonomy, he craves control for himself.

So him and Bif got along well, both being able to give one what the other wanted.

𝕋𝕙𝕖 𝔾𝕚𝕣𝕝

Pinky and Derby grew up together. Their personalities sparked off each other well, and as kids, they gave each other comfort and normality within their controlled environments.

After the Harringtons were caught marrying off siblings, they decided to take a bold approach to the scandal. They admitted to the accusations, doubling down and publicly betrothing Pinky and Derby.

Pinky took one extreme, of rejecting her status and wealth in an act of defiance. And Derby took the other, complying with everything that was asked of him, desperately trying to become who he was supposed to, fearful of his sense of self unravelling if he didn't.

It destroyed their friendship.

I wanted to make sure Pinky didn't end up with the role of the 'evil jealous girlfriend' that many pieces of queer, male media tend to reduce women to - she is just as harmed as Derby within the arranged marriage and is not accidentally or purposefully trying to hinder their relationship.

𝕋𝕠𝕩𝕚𝕔𝕚𝕥𝕪

Now this isn't supposed to simply be a tale of doomed male lovers. Their interactions can and do result in other's suffering just as much as their own.

Derby often orders Bif to do horrible things, Gord being a main target of his intimidation, humiliation, and even physical violence. Derby's even gone as far as to order Bif to break his nose.

His lust for control goes beyond Bif, he wants anything and anyone he can get under his thumb.

And Bif's no saint either. He is not under any pressure to do this - nor can Derby do much if he refuses. But he chooses to follow him regardless, falling for him.

The two are so caught up in their own desires, that they knowingly harm others in the process of obtaining them.

𝕋𝕙𝕖 𝕄𝕚𝕕𝕕𝕝𝕖

When Jimmy first begins to hang around the Preppies, it's thanks to Gord. He desperately gets Jimmy to stay, hoping that his presence will solve his own problems.

Bif is clearly much stronger than Derby, but he would never use it against him - and this is something Derby loves. The idea of having full control over a man that could theoretically do anything he wanted to him (but doesn't) fuelled Derby's power complex

Derby becomes aware of Bif's feelings, stringing him along as a way of gaining more power over him. And Bif gladly accepts.

Nothing is ever hidden, yet nothing is ever spoken.

𝔹𝕠𝕩𝕚𝕟𝕘 𝔻𝕒𝕪

Once Bif is beaten by Jimmy in the ring, and Derby's status at their leader falters, something strange happens. Bif drags himself to the bar, expecting a berating. But Derby instead, patches his bleeding face. (albeit poorly)

Bif rejects this, he doesn't deserve it after loosing the fight, but Derby ignores him, chucking him an ice pack before walking away.

This marks a shift in their relationship. Derby's silent aid was a new form of punishment, and he would continue this for the days to come.

ℂ𝕒𝕣𝕖 𝕒𝕟𝕕 ℙ𝕦𝕟𝕚𝕤𝕙𝕞𝕖𝕟𝕥

Derby's new way of getting under Bif's skin was working. After his loss, Derby would show him more and more affection. Affection that he felt he didn't deserve.

It made Bif squirm, and Derby was more than happy to abuse his new found power. But it soon became too much for Bif, and after everyone has left the club, he snaps.

The things left unspoken were finally said out loud. Bif laments of Derby's new method of torture, and Derby decides to allow Bif a chance to change it. He tells Bif to do anything to him, and Bif almost does, but he can't. Derby, despite giving the order, is uncomfortable, and Bif can't allow himself to give himself what he wants, even if it was an order.

Bif leaves, and they both know he'll be back, but the air around their relationship changes.

𝔸𝕗𝕥𝕖𝕣𝕞𝕒𝕥𝕙

Bif changed. He is still crumbled at Derby's scraps of kindness, and still followed his every word, but his friendly demeanour towards Derby is gone. His love is still their, but his friendship is gone.

This begins to drive Derby insane. Their transaction hasn't changed, so why was he getting so uptight over their shift in freindship?

His relationship with most of the Preppies had soured after the fight, most had stopped hanging around in Harrington House all together. Finally, thing started to get to him, and it started to unravel him.

𝕋𝕙𝕖 𝔹𝕠𝕪

Amongst all the animosity that Derby received from his clique-mates, there was still one that would give him the time of day, Justin Vandervelde.

Justin was starting to come to terms with his own feelings - a lack of attraction to girls, his fascination with the Jocks, and his unrequited admiration to Derby left him in a difficult spot.

Justin knew of Bif's affections; they were the same as his, so why did Derby never give him the time of day? And even after everyone else rejected him, did he not show him the same affection he once showed Bif?

Sure, he had to leave Harrington House with the others - his friendship and status among them was still important. Did he have to throw them away too for Derby to finally look his way?

𝔸𝕟 𝔼𝕞𝕡𝕥𝕪 ℍ𝕠𝕦𝕤𝕖

Harrington House was since abandoned by the clique, leaving behind Derby and Bif. Bif had stayed, he had to. Despite everything, his heart wouldn't allow him to leave Derby behind.

Derby takes advantage of this, giving him orders to help him with mundane tasks, evolving into him something asking Bif to simply help him tighten his tie, or keep him company.

And over time, they were able to build their relationship back. But despite them beginning to talk, laugh, and joke even more so than ever before, Bif would only be there because Derby ordered him to.

Meanwhile, the other Preppies were starting to get into hot water. Without a leader, they struggled, and it ended with Gord pissing off Johnny Vincent and the Greasers, reigniting their turf war.

Bif, who was still friends with them, would often leave to aid in their problems. And Derby wanted to order him to stay, but he started to feel a twisting in his stomach, a pain in his heart, and an awful itch in his brain.

Derby felt guilty.

So no matter how painful it was, he stopped giving Bif orders. And Justin noticed, offering to spend time with Derby in his absence and Derby accepted through lack of any other person that would tolerate him.

Bif eventually became jealous. He begged for Derby to tell him to stay, order him to spend more time even if he felt he didn't deserve any of it. He would do anything to stop Derby from being bored of him.

But Derby wasn't bored, the opposite in fact. And he finally made that clear. But their moment was cut short by a phone call - Gord had been ambushed by Greasers and needed help.

Bif had to leave, but a promise was made that they would hang out again. And not just on Derby's orders either.

𝕋𝕙𝕖 𝔼𝕟𝕕

Derby and Bif's relationship slowly began to mend. And soon, so did Derby's with the Preppies. After all, Derby was a good leader, even if he was a crummy friend.

He helped them properly instigate a counter on the Greasers, even allowing Gord a proper shot at being in charge.

As for him and Bif? Well it started out rough, they still had Derby's engagement and their family's linage to worry about, but things were able to click into place. And Derby was able to explore his own self with encouragement and help from Bif, and even some of the other Preppies too.