A/N- My first attempt at a Charmed fanfic. And it's not going to be a very happy one. Or a very long one. One shot.

This hellhole of his life began six years ago, after Prue had quit her job at Buckland's. Jack still dressed semi-appropriately for work. He came into the office every day. He chatted with old rich people about their fancy statues and paintings and whatever else they wanted appraised. But it wasn't the same.

After a while he couldn't take working there anymore. He missed Prue. He moved out of his apartment in San Francisco and moved into one in New York. He got a job in a boring office. There they made him dress a little more appropriately and use proper office etiquette. He really hated that job, but there was no way he was going back to San Francisco.

Five years after he moved out east, he couldn't take it anymore. He missed San Francisco. He even missed Buckland's. But most of all he missed Prue.

He decided he should move back to San Francisco. He moved back to the same building his old apartment was in. He got his job back at Buckland's and he got his old office back. But still, it wasn't the same without Prue.

A year later, he got up the guts to ask Prue out. Was she now married? Did she have kids? Did she still remember him? Did she even live in San Francisco anymore?

He went to the Halliwell manor. He rang the doorbell. His heart was pounding. What if she didn't live there anymore? What if she had a husband and four kids? What if she didn't remember him? What if she didn't want to remember him?

Her sister answered. She looked a little puzzled. She probably didn't remember him. He knew that he didn't remember her name.

"Your Prue's sister, right?"

"Um, yes I am. Phoebe."

"Oh yeah, I remember you."

"You look familiar? Who are you?"

"I used to work with Prue. I'm Jack."

"Oh yeah. You're that guy who was always hitting on her."

"Yep that's me. Anyway is Prue here?"

"Oh, I'm sorry, but Prue actually passed away six years ago."

And with that, Jack walked back to his car. He could tell that this hellhole of his life was not about to improve.