A/N: I don't own Timeless or its characters. I just decided to finally borrow them for a little bit and have some fun. This is my first Timeless fic so hopefully it's okay. I've promised myself that I'd write at least one before Season 2 and I had this fun little idea that would combine 2 prompts from the "Septober" Contest from Tumblr: "Story must open with the line: 'Wyatt, you look like hell.' & 'Halloween.' Hope you guys like it. Let me know what you think.

*ducks down behind a wall and slowly peers over*

Halloween

"Wyatt, you look like hell."

"Ha. Ha. Thanks," Wyatt returned deadpan, "I haven't heard that like twenty times on my way over here."

Wyatt was dressed as a devil. In one hand he held a pitchfork and in the other he hauled his devil tail through the door. Red horns rested on his head.

Lucy, Wyatt, Rufus, and Jiya decided that they should have a Halloween party amongst the four of them as an attempt at normalcy after all their time hopping chasing after Emma in the Lifeboat. As Rufus had the most room at his mom's house, they decided it best to have the party there. Rufus' mom and brother were at their own respective Halloween parties for the night so they had the place to themselves. Wyatt was the last to arrive.

"Sorry, but you do look like hell," Lucy tried and failed to hold back her snicker. She fixed her red and gold scarf around her neck, careful not to bend her wand. She was dressed as Hermione Granger. Her eyes raked over Wyatt's form while he was distracted talking to Rufus. She had to admit, though not out loud, that he did look an odd mix of adorable and hot in the costume.

"That's gotta be hell to wash off," Rufus couldn't help but add as he shuffled past a seated Lucy with both hands full. In one hand was a bowl of candy and in the other he set down a six pack of beer he just retrieved from the fridge. Rufus elected to dress as a zombie. He set the candy and refreshments down and slipped a fake axe on his head. It was a headband made to look like an axe was embedded in his head.

"You two have enough of the hell puns yet?" Wyatt asked.

"Hell no," Rufus smirked. After a beat he looked to Lucy and then back at Wyatt, "Okay, I'm good now."

"I would've thought you'd dress as an army man or GI Joe or something," Jiya entered the room. She went a simpler route and dressed as a cat. Black felt ears sat on her head and whiskers and face paint adorned her face. She wore a black dress and a cat tail, completing the look.

"That wouldn't really be a costume for me," Wyatt shrugged. He made his way further into the room and took a seat next to Lucy.

"Don't get any paint on the couch. My mom will kill me," Rufus called back over his shoulder.

"I'm not," Wyatt called back as he shifted in his seat so he wouldn't.

Lucy subtly raked her eyes over Wyatt once again. Who could blame her? He was shirtless. His torso was covered in red body paint as was his face and neck. His blue eyes popped in contrast to the devil red. He wore black butterfly jeans and black boots. His spiked devil tail sat next to Lucy practically touching her Hogwarts robes.

"So how come you decided to dress as a devil, Wyatt?" Jiya sat on the arm of the couch next to Lucy as she popped a miniature 3 Musketeers bar in her mouth.

"It's Halloween," Wyatt shrugged, "I thought it would be fun. I had a bunch of red face paint from one year when a couple buddies of mine dressed as Native Americans, but after our time in 1754, I think I had my fill."

"What exactly did happen to you guys in 1754?" Jiya asked.

"Don't ask," the Time Team all replied at once. Jiya put up her hands in mock surrender and left it alone.

"Plus, I wasn't about to take a suit from the wardrobe at work and dress as Greg Brady or something. With all our time traveling, it's like we dress up every day."

"I can understand that," Lucy agreed, "I felt like a Stepford wife when we traveled to 1954 in that blue dress."

"You looked nice though," Wyatt said.

"Thanks," Lucy gave a shy smile. Thankfully her mane of curls to complete her costume hid her blush. They hadn't really had the luxury to continue their conversation about possibilities the day she found out the truth about her mother and Rittenhouse. Emma kept getting in the way – not to mention her insecurities. Wyatt was still in love with Jessica, right? Then there were times like these when he'd compliment her and she couldn't help but wonder how he actually felt. They were a mess.

"Let's put some life into this party," Rufus was over by his stereo. Michael Jackson's Thriller burst through the speakers.

"Excellent choice!" Jiya got up and wound her arms around Rufus' waist, "Let's do the dance."

"No," Rufus shook his head.

"Oh come on," Jiya laughed, "You told me once that you knew how to do it… now's the time to show off."

"Yeah, come on, man," Wyatt encouraged him.

"We'd love to see it," Lucy agreed.

"Only if you guys do it with me," Rufus replied.

"I would but I don't know it," Wyatt shook his head. Rufus looked to Lucy who just shrugged a sorry.

"I'll do it with you," Jiya was already moving the furniture so they'd have more room. Wyatt got up and turned the volume up on the stereo just as the music got to the main zombie dance portion of the song.

Rufus and Jiya were in perfect sync as they performed the choreography. Lucy and Wyatt exchanged looks. They had definitely been practicing. Rufus looked perfect with his zombie make-up. The more Lucy looked at his outfit, the more she realized that he wasn't just dressed as any zombie, but as Michael Jackson's zombie from the music video – red leather jacket included.

The song ended and Wyatt lowered the volume so it was more background noise as the Monster Mash started to play.

"You two practiced that, didn't you?" Lucy asked.

"Guilty," Jiya grinned, "Did you guys like it?"

"Yeah," Wyatt nodded and Lucy continued, "You guys were awesome. I had no idea you could dance."

"It's the only other real dance that I know besides the Robot and the Running Man," Rufus plopped down in a chair next to Lucy, "Thriller is really only appropriate to do on Halloween."

"Well you guys looked great," Lucy patted his knee.

"Who wants to play a little Halloween game?" Jiya reached over behind the couch to retrieve a Jack-o-Lantern-faced bowl full of folded pieces of paper.

"What kind of game?" Wyatt now sat on a chair, leaning forward slightly as to not get any paint on anything. He hadn't had the pleasure of meeting Rufus' mother yet but he did not want to risk her wrath if he actually did end up ruining any of her pristine furniture.

"Halloween Truth or Dare," Jiya held up the bowl, "We go around and pick out pieces of paper that either have a truth or dare on them."

"What makes it Halloween Truth or Dare?" Lucy asked.

"They're themed," Jiya said.

"I'm game," Wyatt agreed.

"Sounds like fun," Rufus took the bowl from his girlfriend and took a seat on the floor, sitting Indian style, "And I'm not just saying that because we spent a few hours coming up with Halloween-themed truths and dares."

"Come on, guys," Jiya gestured for them all to take a seat in a circle on the floor. She sat next to Rufus. Wyatt sat next to Jiya and Lucy took the remaining spot.

"I'll go first," Jiya pulled a paper out, "I got… dare."

"Oh, we started out fun," Lucy clapped.

"What does it say?" Rufus asked.

Jiya read from the card, "Dare: choose to either talk like Count Dracula for the rest of the evening or howl like a wolf every time somebody says "Halloween" tonight."

"I know which one I'd choose," Lucy remarked.

"What's it going to be, Jiya?" Wyatt quirked an eyebrow.

Jiya remained tight-lipped and just slid the bowl over to Rufus.

"I guess we'll find out as the night goes on," Rufus took his paper, "I got a dare too… Dance to Michael Jackson's Thriller."

"Done."

"Uh-uh, you did that already. No fair. Take another one," Lucy picked another one out for him.

"Fine," Rufus took it from her, "I got a truth: What is your favorite candy?"

"That's supposed to be a truth?" Wyatt scoffed as he took a sip from his beer. Lucy jumped slightly from hearing his voice from above her. She hadn't even noticed him getting up to get a drink. He nudged a bottle against her shoulder, silently offering her one. She nodded a thank you and took her own sip as he took a seat next to her, his arm resting on the seat of the chair behind her.

"Dude, seriously, if you get any red paint on my mom's furniture, you'll wish you were back in that shootout with Bonnie and Clyde," Rufus jabbed a warning finger in his direction.

Wyatt theatrically raised his arm off the chair and slowly rested it on his raised knee instead.

"Well, Rufus," Lucy looked expectantly at Rufus, ignoring the fact that Wyatt was leaning more in her direction due to the tail on his costume. He had long ago set his pitchfork down next to the couch. God, she was worse than a schoolgirl with a crush. His close proximity and that costume was playing hell with her emotions.

Guess she wasn't done with the hell puns.

"What is your favorite Halloween candy?" Rufus read the full truth on his card.

Jiya broke out into a howl. And Rufus broke out into laughter. That answered that question. He purposely didn't read the word Halloween at first just to test out his theory of which dare Jiya chose.

"Oh, I'm gonna have so much fun with that on this Halloween night," Rufus grinned. Jiya howled again while simultaneously smacking the Lifeboat pilot.

"My favorite Hal-" Rufus started again but stopped when Jiya raised her fist again threatening to punch him, "My favorite candy would probably have to be a Kit Kat."

"Me too," Jiya said, "That and maybe 3 Musketeers."

"Your turn, Lucy," Rufus slid the bowl over.

Lucy closed her eyes and plunged her hand into the bowl, making a show of mixing the papers up before pulling one out.

"Truth," Lucy read.

"Damn, would've loved to see you howl," Wyatt laughed.

"So what's the truth?" Jiya prompted Lucy. She could tell the effect Wyatt's inadvertent double meaning had on her. Wyatt and Rufus, of course, were oblivious.

"Two part question: What's your favorite Halloween memory? What year was it?" Lucy read. Jiya let out a small wolf howl.

"I don't know," Lucy said, "I haven't really been to too many… masquerade parties."

Lucy caught Jiya's eye and made sure not to say Halloween too many times. Jiya gave her an appreciative smile. She might have been better off talking like Count Dracula instead.

"Come on, you mean you haven't gone to Hallo-" Wyatt looked to Jiya and took pity too, "To masquerade parties before?"

"Being the history geek, I wasn't invited to that many," Lucy shrugged.

"You mean you didn't go to any when you were younger?" Jiya asked.

"Maybe a few, but they mostly consisted of my classmates getting drunk and vomiting up candied apples the whole evening," Lucy said.

"There had to be a good one," Rufus said.

Lucy looked up, thinking, "Well, there might have been one."

"Knew it," Wyatt smiled, "When?"

"It was 1999," Lucy began, "I wasn't quite sixteen years old. I met this guy…"

1999

Lucy Preston looked around at her classmates and friends as she slowly entered the "haunted house." She didn't even want to come to the party, but her mother told her she'd regret it in the future to not experience "being a teenager." Plus, her little sister Amy at only 9 years old had been to more Halloween parties than she had.

She straightened out her flight jacket and her make-shift hat made to look like a helmet. She didn't care that her friends probably wouldn't get she was dressed as Amelia Earhart, but she thought it was fun. Plus it was educational and historical. She loved history. Looking around, she saw a couple Darth Mauls from the new Star Wars movie and quite a few people dressed as Neo from The Matrix. Making her way over to the punch bowl, she figured she'd stay long enough for people to recognize that she actually showed up and they wouldn't give her a hard time about it at school.

Scanning the crowd, her eyes landed on an unfamiliar boy drinking punch by himself in the corner. He looked just as uncomfortable being there as she did. He was dressed as Zorro. The little black mask did nothing to cover up his baby blues. He was cute.

"Lucy!"

Lucy jumped and turned to her friend. She popped out of nowhere, "Oh, hey, Bex."

"I knew if I bugged you enough, you'd come to the party," Bex smiled, "It's about time."

"Yeah, well I finished all my homework," Lucy replied.

"Who were you looking at?" Bex asked.

"Nobody," Lucy blushed and brushed a stray hair behind her ear.

"Was it that hot guy dressed as Zorro?" Bex knew. Lucy darted her eyes back and forth but kept quiet.

"Go over and talk to him," Bex encouraged her, "I hear he's only visiting California anyway. I think he's from Texas or something. Go get him."

"I don't know, he looks busy," Lucy shook her head.

"Oh yeah, he looks super busy," Bex drawled sarcastically. She gave her a push, "Go."

Lucy looked back to her friend. Deep down, she knew she could never say no to her. Plus, she had a point. She did want to go talk to him.

"Hi there," Lucy spoke up so she could be heard over the music.

"Hi," the guy nodded. They stood in awkward silence for a moment, music playing in the background.

"You having fun?" Lucy tried to start a conversation.

"It's all right," the boy replied. Bex was right. He had a slight Texas drawl. And damn it if that didn't make him cuter.

"Are you new to school?" Lucy asked.

"Just visiting some family. I'm from West Texas," he replied, "My cousin is somewhere around here. He made me come tonight. He says I should get out more."

"I'm from here," Lucy replied, "Well, not from here here. I mean, this isn't my house or anything. I meant I'm from California."

Lucy took a nervous drink from her punch. And bless this guy. All he did was smile. The left corner of his lip went up in a half smirk.

"You want to dance?" he asked.

"S-Sure," Lucy put her drink down. He took her hand and gallantly led her to the dance floor. They sure had manners down in Texas. All Star by Smash Mouth started to play. They both began to move to the music, slowly starting to let loose.

"I like your costume!" he shouted over the music.

"Thanks!" Lucy held her hat/helmet on her head, "I like yours too."

"Amelia Earhart's pretty cool," he danced a little closer thanks to some guy behind him in a bulky costume.

"You know Amelia Earhart?" Lucy's voice went up in surprise.

"Yeah," he said, "Female pilot – first one to fly solo over the Atlantic Ocean. That's pretty cool."

"She was pretty cool," Lucy smiled.

They danced for a couple more songs all the while talking about movies and occasionally some historical facts. They bonded over mutual knowledge and love of James Bond. Before they knew it, the party began thinning out as people were leaving. There were only a few people dancing besides them. The songs started to slow down. I Don't Want To Miss A Thing by Aerosmith played over the speakers.

Lucy looked up in his baby blues. He moved his hands to rest at the small of her back as she wrapped her hands around his neck, locking her left wrist in her right hand as they swayed to the music. As the closing notes filled the air, Lucy closed her eyes, leaning forward as his head dipped down. Their lips were a hair's breadth apart when the music came to a dead stop and the lights flashed on overhead.

"Sorry, guys," one of the girls dressed as Britney Spears from the …Baby One More Time music video apologized, "Party's over. My parents told me I could only keep the party going until eleven. It's eleven. See you guys at school."

Grumbles echoed all around as people started heading out. Lucy just numbly looked up at Zorro, as she started to call him in her head, "I, uh… it was nice talking with you."

"Yeah," he breathed, "Hey, would you like to…"

"There you are man," another guy came up behind Zorro, "We better head home. Gramps will kill me if I keep you out too late."

"Just give me a second," Wyatt Logan was ready to kill his cousin – just when he met a cool girl who wasn't into herself more than him. He turned back around to apologize and ask for her number, but she was already gone.

"And I never saw him again. Never found out his name," Lucy finished her story with a shrug, "Anyway, I guess that was my favorite Halloween memory. It was 1999."

"That was so sweet," Jiya gushed.

"You didn't howl," Rufus pointed out, "She said Halloween."

"Shut up, Rufus," Jiya smacked him, "Wasn't that sweet, Wyatt?"

Wyatt swallowed. All these years and his mystery Amelia Earhart was Lucy. He had only been in town for a couple weeks visiting his cousin when he dragged him to a Halloween party. He was having a terrible time until a girl dressed as Amelia Earhart came up and started talking to him. He was an inch away from having his first kiss when his cousin pulled him away. How could he forget about that? And it was Lucy? Looks like fate might actually be real.

"Yeah. Yeah, that was sweet," Wyatt replied quietly, "Hey, Rufus, could I talk to you for a second?"

"About what?" Rufus popped a few popcorn kernels in his mouth.

Wyatt didn't bother answering. He just pulled Rufus up and dragged him off to the side with an "Excuse us for a second, ladies."

"Dude, what's up with you?" Rufus shrugged Wyatt's hand off his leather jacket. Wyatt peered over Rufus' shoulder to look over at the girls. They were engaged in conversation, not paying them any attention.

"I'm Zorro," Wyatt said.

"I'm pretty sure Zorro wasn't red with horns and a tail," Rufus returned.

"Rufus," Wyatt gave him a look, "From Lucy's story. I was Zorro."

"What?!"

"You guys okay over there?" Lucy called out to them.

"Yeah!" Wyatt called back.

"You're the Zorro from her story?" Rufus asked at a normal volume, "You knew Lucy when you guys were teens?"

"I didn't know it was her," Wyatt said, "I never knew her name. I hadn't really thought about it since then. I met her before I even met Jessica. Hell, Lucy was almost my first kiss."

"It's a small world," Rufus shook his head in disbelief.

"Would you mind if I used your shower?" Wyatt scratched.

"Whyyy?" Rufus eyed him up and down. That was a random question.

"I want to wash off this body paint," Wyatt said.

"Oh," Rufus said, "Yeah, sure, man. Go ahead."

"Plus that'll give me an excuse as to what I wanted to talk to you about," Wyatt said, "Don't tell her I was Zorro yet, okay, Rufus?"

"I won't say a word, I promise," Rufus said, "I've been rooting for you two for awhile now. Plus, if you get together tonight, I'll be the closest in the pool."

"What pool?" Wyatt stopped short from turning to head to the bathroom.

"Nothing," Rufus looked innocent, "Nothing… just go wash that stuff off and then go get her, you devil."

Wyatt gave him a look.

"Couldn't help it," Rufus shrugged. There were just too many puns he could make with Wyatt dressed as a devil. Rufus headed back to Jiya and Lucy.

"Wyatt okay?" Lucy asked when only Rufus came back into the living room.

"Yeah, he just needed to wash off the body paint," Rufus gestured back to the bathroom, "It was starting to get a little itchy."

"Oh," Lucy accepted the excuse. The trio fell into comfortable conversation.

Meanwhile, Wyatt managed to wash off all the red body paint. He looked at himself in the mirror once he was dressed again. His skin was a little pink from both scrubbing off the paint and from the heat of the shower. His mind was racing. Lucy happened to be the girl he hadn't thought about in over a decade. She also happened to be the woman he couldn't stop thinking about now. After he allowed himself to accept Jessica's loss and open himself up to possibilities, Lucy invaded all his thoughts.

What was he going to do about this revelation? He wanted to address their conversation about being open to possibilities for awhile now but something always got in the way. Between hopping back in time, chasing after Emma to simply choking on his own fear, they just hadn't gotten around to talking about it. Lucy was even his next door neighbor now after she moved out of her mother's house after she revealed herself to be Rittenhouse. They spent time over at one another's apartments, watching movies, hanging out. Occasionally they would spend the night on each other's couches, and yet whenever he gathered up the courage to bring up the possibility of them pursuing a relationship, she'd be asleep or they'd get a call to come into work. Put simply, he always chickened out.

He let out a sigh. No more stalling. It all started on Halloween back in 1999 without either of them realizing. It would be fitting for it all to begin again on Halloween and amongst their friends. Grabbing a spare shirt of Rufus' that he hoped he wouldn't mind he was borrowing, he made his way back out to the party.

"You look better," Lucy commented when she saw him return.

"You had to pick a red shirt?" Rufus noticed.

"Hope you don't mind," Wyatt said, "I was getting a little chilly."

"You're fine, man," Rufus assured him. He gestured to Lucy with his eyes in silent support. Wyatt took a seat next to Lucy on the couch after giving Rufus a slight nod. She was still chatting away with Jiya.

"Hey, Wyatt, you never took your turn," Jiya shuffled the bowl in front of him, "Might as well finish the game."

"Yeah, no skipping out," Lucy agreed.

"Okay," Wyatt smiled and reached into the bowl in Lucy's outstretched palms.

"What'd you get?" Lucy asked.

"It's a truth and a dare," Wyatt said.

"But we didn't-" Jiya started, but Rufus hushed her subtly.

"Okay. What's it say?" Lucy didn't hear Jiya.

"It says: What's your biggest Halloween regret?" Wyatt wasn't even looking at the card.

"What about the dare?" Lucy asked.

Wyatt's eyes darted down to Lucy's lips. Just as he had in 1934, he reached out and grabbed Lucy, their lips crashing together. Rufus and Jiya looked on with smiles. In reality, the kiss lasted a couple of seconds, but to Lucy and Wyatt it felt like a blissful eternity.

They slowly pulled apart. Lucy licked her lips, "S-So, what was your biggest Halloween regret?"

"That," Wyatt whispered.

Lucy furrowed her brows.

"I was Zorro, Lucy," Wyatt said.

"What?"

"That was me," Wyatt repeated, "In 1999, at that party. My cousin dragged me to that party. I was having a terrible time and was about ready to find my cousin and tell him I was going to just meet him back home. Then this girl comes up to me dressed as Amelia Earhart. I figured I'd let her say her piece and I'd politely dismiss myself and go home. But she ended up being amazing. I wanted to ask her out, get her number for whenever I might happen to be in town again… but before I could, she disappeared."

"My biggest regret I've ever had on Halloween was not kissing that girl for all it was worth."

"Well, now you have," Lucy smiled.

"So… Baby Doll," Wyatt grinned at their inside joke, "Would you go out with me?"

"Absolutely," Lucy cupped Wyatt's cheek, "Shweetheart."

They chuckled before once again sharing a kiss.

"Any clue what those pet names were about?" Jiya asked her boyfriend.

"Not a clue," Rufus shook his head, "But I guess this means that I win the pool."

"Money I'll happily give if it means they're finally together," Jiya leaned in on Rufus' shoulder.

Wyatt and Lucy were blissfully unaware of Rufus and Jiya's conversation – lost in each other. They could talk all they wanted later. As for now, they had a little over a decade to catch up on. Lucy might not be that far off about fate.

Rufus took Wyatt's discarded card to see what was written on it. All it said was "How old were you when you first went Trick-or-Treating?" Rufus reverently shook his head at his best friends and leaned over to give Jiya a peck on her cheek. Overall, he had to admit – this was a successful Halloween party. They should do it again next year.

The End

A/N: Okay, well, that's all I wrote. I hope you guys liked it. I thought it would be fun if Wyatt and Lucy met before without either of them realizing it and found a way to weave it into the story. Let me know what you thought! I can't wait for Season 2 next year. Hopefully if you guys are interested and I have enough free time and inspiration, I might get a chance to write more Timeless stories. :)