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Simon remembers his first-ever interactions with you. It was just a usual GTA game with his friends, but this time you were added as well. He did not think much of you at first and just enjoyed your comebacks when the other guys were tryna give you shit for being bad at the game.
The friendship between the two of you has always been mostly chill. When you both started living in the same house it took him a bit to get used to you, but that was inevitable and would be easily conquered with time.Β
One of Simonβs favorite things to do with you is to jokingly go after someone else with you. It is known that he is a bit evil. But when it comes to you most people remember your kindness rather than the same mischief you possess as well.
When the both of you start tearing at someone with those goddamn smart remarks there is no escape or a way of defense for the victim. There is always a shock in the person's eyes when you join Simon cause even though you have done it so many times they still find it surprising. And Si finds it extremely amusing.Β
The most often victim of the two of you would be JJ. There is a compilation on Youtube titled βY/N and Simon gangbanging JJ for 16 minutesβ that got too many views for that title alone.Β
The playful beef between the two of you is nice too. The both of you know each other well enough to be aware of what topics are off-limits and know that the other will not bring them up. It is just pure fun, such a comforting simple joy to have in your life with your dear friend.Β
It has also become a habit to gently annoy each other physically. So whilst Simon pinches your sides or tickles you, you flick the back of his head or rough up his hair a bit.
Little poking battles will occur even when you tell him that he should stop this kind of behavior since he is soooo old now. But Simon knows well you do not mean it and pokes you twice for calling him old.Β Β
Simon was glad that you got along with Talia until you and her started teasing him together just like you and he did to others. He was betrayed and needed some time to recover /hj.Β
He is very supportive of you. Encouraging your ideas and goals. Congratulating you on your milestones and accomplishments.
The two of you would sometimes go on late-night drives. They had no strong purpose, just to rest your minds from making content and editing. Every so often you would capture him in his driving glasses on camera knowing that it will drive the fangirls crazy.
You also helped him with being a good boyfriend sometimes. He was not doing badly on his own, but you would sometimes give small pieces of advice in aspects where he was a bit clueless. He just needed some assurance as well lol.Β
So many cameos in each otherβs vlogs.Β Mostly just fooling around or randomly jumping in the frame.
'Subscribe to Miniminter on youtube.'
'Don't, go leave a dislike instead'
'HEY!'
When you were younger you used him for his age. He got you energy drinks (no alcohol promotion on this blog) and one time he accompanied you to get a piercing which you were oh-so thankful for.
It was a condition that a parent had to be present, but you convinced the person that would do the piercing that any adult would do since youβre parents were far away. Josh and Tobi both said you were too young, but the third time was a charm and Simon agreed.
When they were getting it done Simon held your hand, but also laughed at you on the same time.
Dying his hair some kind of crazy color for a video, only for the color to not exactly fit him. (Atleast the color is even because you applied the dye instead of him-)
You have so many nice memories with the guy. Like the other brother/the brother you never had.Β
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Hope you liked these headcanons and that you have a sunny day or night π€!!