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Simon would enjoy your persona a lot. Finally, someone who can appreciate his dark humor and reciprocates them as well!
He can always count on you to get the job done and lighten the mood while you're doing it.
Your jokey attitude and squeaky voice is definitely a breath of fresh air for him.
You're the polar opposite of him, loud, full of emotion, always finding a way to laugh at something, and he loves it. You're the one that makes him loosen up, slowly taking him out of his shell.
He's very glad he doesn't have to watch out for you, he's seen you get out of plenty of difficult situations in the most creative ways. Before that he had worried for you, but you've proven yourself dozens of times, so he's not as concerned as he used to be. (He still likes to cover you from far away with his sniper. c;)
When he first met you off the field, he avoided you like the plague. Your loud personality just made his anxiety go haywire.
On the field however? You make the perfect team.
The two of you work flawlessly together. Ruthless, out of your minds, enjoying the moment.
After the first mission together, you became inseparable. You didn't do many things without the other. Morning workout? Spotting each other. Breakfast? One of you is making it for the other. Missions? You always figure out a way to be sent off with him.
At some point you even make a competition on who can take out the most people, or who can kill someone in the most creative way.
You make his anxiety better somehow. You're so out there and all over the place, that he doesn't really worry about how he comes off to you.
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I also made art for this:
