How did you guys met?

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Herman:
You were new to Springfield, after getting fired from your old job you decided to move towns to get a new job.
While walking around, you noticed an antiques shop and being the curious person you were you entered the shop.
You looked at one priceless tea set, while examining the tea cup someone yelled "Hey," causing you to drop the tea cup breaking it.
You looked over your shoulder and saw a man taller than you, he had only one arm and his face was in a scowl.
"Be more careful, now you gotta pay for it," he snapped.

"Well sorry, but I don't have any money," you told him.

"Well, why don't we have a deal, work for me until you finally paid up," he proposed.

"Fine," you spat.

Ever since that day you have been working for the man named Herman.

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Snakejail Bird:
You were a wanted criminal in Springfield, the police and town were so desperate to find you.

One day you let your guard down, trusting a fellow prison mate, lead to you being caught.
You were once again thrown back into prison.
While in Prison you made a perfect plan to escape, after getting almost all of the tools, you have come to realization you need a certian tool.
You heard from
your cell mate that another inmate had that tool.
You looked for the specific inmate, you heard that his name was Snake jailbird ot something.
You happened to bump to him and asked him for the tool.
He at first refused, but when you made the deal, he accepted.

"The deal is if you give me that tool, with it, we can leave this place,"

"A deal is deal" he agreed as he gave you the tool.

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Otto:
You were the vice prinpical of Springfield Elemantary.
Because of that you were always picked on by the bullies.

'An adult getting picked on by some teenager boys, how silly of me,'
You will always think to yourself.

One day your car broke down and you had to take the school bus.

'If things couldn't get any worse,'

You thought to yourself.

Once the bus stopped at your block you got on.
You decided to sit in the front seat behind the bus driver.
He seemed very friendly and started to make some small talk with you.

"Hey aren't you Mx. (L/N)?"

"Yeah, that's me,"

"Why are you riding the school bus?" He asked.

"Well my car broke down and I don't wanna walk,"

"Well that sucks, anyway maybe I can see that car of yours and maybe try to fix it,"

"You really wanna help me?"

"Yeah,"

"Oh thank god thank you so much,"

"No problem,"

The two of you continued to talked until you reached your destination.

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Smithers:
You worked at the SNPP for about 3 years now.
You hated your boss Mr.Burns.
You always wondered why his assistant Smithers liked him.
One morning you got to work early and watched another car park next to yours.

"Hey you're (Y\N) (L\N) right?" Asked Smithers.

"Yeah," you responded.

"Well why are you so early?" He asked.

"Just wanted to get some work done,"

"Well work doesn't start until 2 hours wanna get something to eat?" He asked.

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