I wanted to feel more productive so I wrote some headcanons for my fav bois; Gary, Johnny and Derby. If you happen to like this and want to see more of any of these three, just lemme know ^-^
How they asked their SO to be their girlfriend:
• I imagine that Gary is sort of friends with everyone at school because he can either tell them what they want to hear or constantly insert himself into their lives. You would fall into that latter catergory because Gary just loves picking on you and getting you riled up.
• He knew you didn't really hate him since you hung out with him, Jimmy and Pete on most days in the boys dorm. You guys would usually watch TV or try to beat each other's scores in Future Street Race 2165. Sometimes though, Gary would want the group to get up to some harmless mischief involving various items from Jimmy's chem set.
• Gary would start understanding his feelings when you're hanging out with other people more than usual. He doesn't care if it's with girls or boys, he realizes that he wants you for himself. Who else is he supposed to mess with? Petey? He never fights back.
• Gary might decide to ambush you while you're studying on a bench somewhere. He'd snatch your work before you were able to notice his presence and immediately begin reading over it, nitpicking every little part. When you jump up to get it back, he just uses one arm to hold you back and continues what he's doing with the other.
• He wouldn't have had any intent on confessing at that moment, not until one of the prefects call him out for bullying you. Gary's arm would move around your shoulders to pull you closer instead. ''She's my girlfriend, we're just playing around.'' He'd smile until the prefect went away.
• He laughs when you get all flustered and tell him not to lie about things like that. That's when he'd casually bring up ''Let's just do it for real then'' or something along those lines. He'd try to act like this was no big deal, but would secretly be really pissed off if he got rejected.
• A total mess when it comes to expressing honest feelings. He's used to having that 'tough-guy' image around his friends so letting that go for someone comes with difficulty.
• He doesn't have great self-esteem after his relationship with Lola and probably procrastinated ending things for a long time. Although, she would have to do something pretty extreme for him to lose faith that she could ever be loyal to him.
• He'd start with spending a lot of time around you between classes, maybe helping you out with projects for shop class. But once you become a part of the clique, he'd ask you to hang out with them more casually. Johnny wouldn't let you come along for anything dangerous- like if they were gonna vandalize shit in Old Bullworth Vale.
• As for actually asking you out, he'd make up an excuse to be alone with you. Maybe he'd ask you to help him test out some bikes they've been working on and you two would ride along the dirt paths in New Coventry. He'd definitely show off and jump a couple ramps.
• When you guys took a break and got off the bikes, that's when he'd try to segue into it. Johnny starts off with making sure you know his situation with Lola and that he's completely over that. He wouldn't want you thinking that he was still committed to her and pulling you into the drama.
• He'd be stumbling his way through the confession, awkwardly tugging on the inside of his jacket and trying to put on a calm facade. Johnny's eyes would lock with your's once he actually came out and asked you if you'd 'be his girl'.
• Even without knowing your response, he felt better to have that off of his chest. It was a turning point for him as he could finally tell himself that he was over Lola and could leave that part of his life behind. He at least felt like he was being honest with you but could only hope you'd say yes.
• For Derby to even talk to you, you would have to already be in his social circle. Since you're not related to him, you would either come from money or get brought into the clique by one of the existing members.
• Derby obviously holds himself on a level above his fellow preps and he wouldn't treat you any differently at first. Something about you or your family would need to impress him before he could start paying any attention, he won't spend his time on just anybody.
• But once he considered you a friend, he found spending time with you to be exciting. Since he was expected to only marry cousins and keep their blood 'pure', getting closer to you sparked a more rebellious side to him. In his mind it was thrilling to imagine what a relationship with you could be like, and to completely disregard his father's expectations.
• He wouldn't even consider whether it would be a secret arrangement or not. Perhaps he could get away with it if he found the right way to present it to his father? Either way, he was going to make his own decision for a change.
• Going with his sophisticated nature, he would handwrite you a letter, telling you where to meet him at some extremely cheesy location. It would have to be somewhere that you two could be alone though, maybe in the middle of a romantic rose garden that Derby just so happens to own.
• When you find him and ask why he wanted to see you, he'd ignore your questiones and recite a short poem. That would be the lead up but as he asks the question, he would take your hands in his. Derby's very confident in his efforts to court you and has no concerns that you'll refuse.
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