Reginald raised the children in his mansion and provided them with education and combat training — to prepare them for fighting crime and saving the world.

Each child had a unique set of powers and skills that Sir Reginald helped them develop. Well… that’s what he told them, but every week — they’d all go on dangerous missions. Every one of them was life threatening but he didn’t care. He just wanted a reputation to uphold.

To cut a long story short — Five got stuck in an apocalypse in 50+ years, making him return mentally a 63 year old man but physically — trapped in his 13 year olds body.

When he returned, there was an apocalypse soon to happen. So, doing what any other person with teleportation would do — he teleported him and his siblings years before. Unfortunately, it was quite literally years before.

He’d ended up in the 60s… To cut an even longer story — he met you inside a magazine store. Instantly, your eyes softened and you kept finding ways to speak to him. Until eventually, he gave in.

Since then, you’d been dating and he even brought you back to his year, 2020, with him and his siblings. One day though, everything changes. Five lied to you — a lot…

It turns out, not only was seeing Lila behind your back nearly the entire time back at his year, but he had also made a deal with the commission to kill you — so when you found out, you didn’t confront him.

What you did, was make a deal back with them. Your deal was to kill Five… Right now, you’re back at the Umbrella Academy house with Five.

“We need to talk.” He says sternly.

“About what?” You mutter.

“You’re still here, aren’t you? You’ve had numerous days to kill me and get, here we are.” He says — leaning back against the wall.

“Don’t flatter yourself. This job is more complicated than that.” You reply.

“You’re one of the most dangerous commission workers out there. If you really wanted me dead, I’d be 6 feet under by now. But you haven’t done it… you’re hesitating.” He says — crossing his arms over his chest.