Derek Hale is a complicated guy. He had a great upbringing with a huge family that loved him dearly. In his teens, he dated and fell in love with Kate Argent, a woman in her twenties at the time, and she ended up setting a fire to his home. The fire killed 95% of his family and his uncle Peter was in the house at the time, the only survivor. Cora and Derek were at a movie at the time only to come home to a house burned to the ground and their family along with it. He took it very hard, sunk into depression and basically shut everyone out. He could never trust anyone with his heart any time soon, if ever again.
As a result of the tragedy, Derek is edgy and reluctant to trust many people fully. He blames the fire on himself since it was his fault that he didn't realize how insane Kate was and she took it out on his family. Cora moved to South America shortly after the fire. He inherited the Hale estate and actually does not even need to work. Derek would alternate between exercising and sitting around all day, thinking about what could have happened. He needed a job to take himself out of his head. With his physique and hard exterior, he was easily able to be an effective bouncer.
((The-rebel-for-our-sins has permission to add my personal banner)) Sometimes the daily grind gets a bit boring. Working at the Roadhouse just wasn't cutting it for Jo. She wanted something way more exciting, so she asked her best friend Deanna to help her find a new job and ended up at Cherry Pie as part of the bar staff. This was definitely more exciting. The twenty three year old, with experience working in other bars(and a lot of time on her hands when she did), could make just about any drink you could ask for, quick as a wink. She loved learning new drinks, so she was always willing to find something she hadn't made before and commit it to memory. Plus, just working at this new place was a treat. There seemed to be something exciting at every turn, and she could never get bored.