Emma was most certainly not having fun. The first two days she had been on her own were great. She bought an ipod hookup so she could listen to her music for once (something that hadn't happened since Sam and Dean had dragged her back into the hunting world), went to bars, and did a lot of shopping. She got to just be normal, and best of all, do girlie things. She loved her brothers, but between all of their testosterone and the Winchester's family business, she wasn't always able to just be a girl. She had even gotten her nails done!

Yes, her break had started great. And then, he came along.

Emma was sitting at the bar with an old friend. Since the boys had to go to Little Rock, Emma had decided to visit the nearby city of Jacksonville. She had last been there when she was 15, and her father and Dean were on a hunt. Sam had been sick, so they had decided to leave the two younger Winchesters behind. John had dropped her and Sam off at a motel, told her they would be back in a few weeks, and had then taken off again. On the first day at their new school, Emma had met another new student named Becky. The two had become fast friends despite how reserved Emma usually was. What was funny was how obsessed Becky was with the supernatural. Emma had to always hide a grin whenever Becky mentioned how much she would love to see a ghost.

Although Becky was a bit more…exuberant… than Emma remembered, it was fun to catch up with someone who didn't want to talk about stabbing techniques, or about the pros and cons of a colt 1911 versus a Browning 9x19mm Hi-power.

"It's sooo good to see you again Emma! It's been like, what, a hundred years since we last saw each other?" Becky exclaimed.

Emma smiled. "Close. About ten." She looked at her watch. "Crap! It's almost 12! We've been talking for more than three hours." She grinned at her old friend. "I'm glad I caught you before you moved to Delaware. Guess you better go home and finish packing, huh?"

"Ohmygod, yeah! I can't believe I'm finally getting out of this town! Look, I even got a new book for the flight tomorrow!" She pulled out a paperback novel that had two long haired, bare-chested men on the cover. Across the cover in bold letters was the word 'Supernatural'. Emma had to resist rolling her eyes. It was the exact kind of book Becky had always tried to get Emma to read when they had last seen each other. Emma had never been interested. When you have to live in the supernatural world, it sort of sucks the fun out of reading about it. Books were supposed to be about escapism, anyway, and if Emma wanted to escape into 'another world' it would be into a normal one. But she tried to appear interested for her friends sake.

"So what's it about?"

"I don't know yet exactly, but it's basically about two brothers who-"

Someone interrupted Becky from behind Emma. Someone with an all too familiar, charming voice. "Excuse me, is this spot taken?"

Emma closed her eyes slowly. She took a few deep breathes to steady herself. When she opened her eyes again, she saw Becky's eyes dart from her face to the guy behind her. She had a very sly look on her face as she answered for Emma. "Actually, I was just leaving. You can have my seat." She and Emma both got up to hug each other. "Have fun!" she whispered into the shorter girl's ear. Emma just rolled her eyes.

As she watched Becky exit the building, she waited for the man behind her to sit down. She didn't have to wait long.

"Miss me?" asked the Trickster, raising an eyebrow.

"Nope. Not at all. Why are you here?"

"Awww, I missed you. I actually do enjoy out time together." The Trickster turned to the Bartender. "She'll have a Morning Glory."

"No, she will have Corona."

"Come on, you know you only have beer and shots when you're with your brothers or other hunters. I know for a fact that you love Morning Glories."

Emma glared at him. "You know, it's really creepy that you know that. Have you been spying on me or something?"

The Trickster pretended to think about it. "Hmmm… Yes, as a matter of fact I have been spying on you and your brothers. But the reason I know what drinks you like is because you told me. On our date."

"We did NOT-" Emma began loudly, then cleared her throat when people started to look at them. She blushed a little and then started again in a whisper. "We did not have a date. What we had was a trick to distract me so you could keep on pulling deadly pranks on people. That is not a date. It didn't count." Emma groaned inwardly. She knew she sounded like she was denying it way too much.

Apparently the Trickster thought she was too. "If you say so, sweet cheeks." he said with a smirk.

"If you aren't going to tell me why you're here, I'm going to just leave." She stood up to prove her point.

"Why? Do you want to continue this somewhere more…private?" The Trickster snapped his fingers.

Suddenly Emma found herself and the Trickster in a private room, sitting across from each other at a table. Their table was lit by a pair of candles, with a bottle of wine in an ice bucket in the middle. Emma's jeans and t-shirt had been replaced by a red dress, and her hair was suddenly neatly curled and styled. The Trickster was in a black sports jacket and matching pants.

Emma was outraged. "Are you insane? All those people just saw us disappear into thin air!"

The Trickster laughed. "Don't worry, I'm very good at being invisible when I want to be. Nobody saw anything."

Emma relaxed slightly. "Maybe so, but why are we here, exactly?"

The Trickster pretended to surprised. "You said, we had never been on a date, so this is a date of course."

"Dates usually are prepared in advance. And usually between two people who both want to be on it."

"Yeah, well, most people don't hunt monsters for a living." Emma just rolled her eyes.

"Anyways… I couldn't help but notice you haven't talked to your brothers about what we discussed. You really need to get on that. But," he continued. "That's not why I brought you here. I thought you could stand to have a little bit of fun while the knuckleheads are off playing don't drop the soap."

"I was having fun."

"Pssshhhh. What you were doing wasn't fun."

"It was to me. I suppose you're definition of fun involves a bit more blood."

He smiled. "Among other things, yeah. But in addition to knowing your favorite drink, I also know that you have always wanted to go to Rome." Emma raised an eyebrow.

"Yeah? So?"

"You haven't even asked where we are."

Emma looked at him suspiciously. Suddenly she noticed a pair of heavy drapes. She walked over and lifted them up a little. In the distance she could see the Colosseum. She quickly dropped the drapes again.

"Come on. Am I amazing or what?"


All right, so maybe Emma was having a little tiny bit of fun. Ok, she was having the time of her life. But she felt guilty for every moment. Well, she knew she should feel guilty for enjoying it. After a few glasses of wine, the Trickster had taken Emma on a walk through Rome. He somehow seemed to know Rome like the back of his hand, taking her down hidden side streets and narrow alleyways that all seemed to lead to every sight she had wanted to see her entire life. Emma suspected that he was most likely using some sort of time-space manipulation power to get them there so quickly, (another hint was the fact that no matter how many times she looked at her watch, the time never changed) but she didn't care. She didn't even care that they were breaking and entering into some of the sights, such as the Colosseum.

"How many people get to have their own private tour of the Colosseum?" The Trickster asked as they walked in the hypogeum. Emma just smiled. As she walked in the maze-like arena, she felt a bit of sadness.

"I kind of feel bad for wanting to see this place. Considering how many people died here for other's entertainment and all."

"It wasn't just for gladiators. They also held plays here, and brought animals in, like in a zoo."

"Yeah. But they also killed a lot of those animals in 'hunts'. They even set up scenery to make it look more realistic."

The Trickster just smiled. "They did. But a lot of them got what was coming to them."

Emma was shocked. "No. No way. You were not around back in 80 A.D."

He just kept smiling.

"How old are you?" The Trickster shrugged.

Emma was in awe. The Colloseum, something she had been longing to see since before she could remember, was forgotten. One of the main reasons she had wanted to come to Rome was to see the place where so much history had taken place, and to see a place that was older than she could imagine. But if this man- 'creature' she reminded herself- was even older than this place… It was mind boggling.

"Come on." He said, in a gentle tone she had never heard coming from him, "We got one more place we gotta see."

Author's note- Wow. That was kind of exhausting, I'm not gonna lie. It didn't come out exactly the way I wanted, but I think it's actually pretty good! And yes, that was the one and only Becky at the beginning! I'm really sorry if anybody here doesn't like the character, but I just couldn't resist adding her in for a cameo. And before anyone says anything, when Emma last saw her, Becky never met Sam, as he was in middle school and the girls were in high school, and Emma never told Becky about Dean because he was never there so there was never any reason to, and Emma doesn't like to reveal too much of herself and her family. Which is also why the girls never talked outside of school. I can decide things like that cuz I'm the writer. I don't want to hear any complaining from anyone. (please?)