The Challenge

An: I do not own Arrow.

An: I do not own Arrow. Thank you Laura for your review.

October

Oliver knew Felicity was at a cross road in her life. Her purpose for staying in Las Vegas had been removed and she needed to decide what she wanted to do with the rest of her life. He knew she had contracts with the casinos for tech support. From what he understood, most of those would be up next year and she had been training IT staff at the casinos how to handle problems. Her mother's medical bills and funeral costs had eaten through most of her savings and it was the payments for on-site visits at the casinos that were keeping her afloat. Oliver had intercepted the bills that arrived at the beginning of October and paid them all, including the rent.

Oliver started cutting back on his water and energy usage. He turned off the tap when he was brushing his teeth and he made sure he only turned on the dishwasher when it was full. He turned off the television and lights when he didn't need them. Donna used to do it for him before and it had never quite clicked why she was doing it until now.

Oct -2

The bar was packed in the first week of October for the World Series. His father's baseball team, the Starling City Rockets, hadn't made it to the series. He knew his father would be disappointed. His father used to take him to games when he was younger. It was one of the few times he would have his father all to himself. He knew his father would be following the games even though his team didn't make it so Oliver broke his rule about his phone usage at work and made the effort to send his father a few messages about the games as he watched them. They got into an avid debate about a call an Umpire made at third base. Oliver thought the guy was clearly in, his father disagreed. The slow motion replay revealed his father was right. He vaguely wondered if that was some sort of sign that his father was right about the Challenge too. He had reached the point where he didn't want to image what he would be doing at the moment if his father hadn't concocted this whole scheme to teach him a few lessons.

Bob pulled Oliver aside and he thought Bob was going to scold him about being using the phone but instead he told him that he had received several applications for the new waitress position. He wanted Oliver to come in at 10:00am and interview the applicants and then hire one. He was confused why Bob would want him to choose but Bob said Oliver worked with the waitresses well and knew exactly what their position entailed especially since in the absence of a second waitress it was Oliver who had to pick up the slack. He trusted Oliver to select the right person for the job.

Oct-3

Oliver had twenty applications in front of him and he was supposed to interview all of them between 10 and 3. He felt like Bob had set him up for failure. There were already 8 girls seated in the bar waiting for him to interview them. The night before, Felicity had helped him research how to conduct job interviews and what sort of questions to ask the applicants. She offered to help him with the interviews as well but he had declined her help telling her that Bob had asking him to do it, so he would do it.

The first five applicants all hit on Oliver. He thought that was not appropriate behaviour for an interview so he cut them off his list. The next two girls where college graduates who were looking for jobs to tide them over until they could find something better, he crossed them off as well. He thought five of the applicants were addicts looking for a source of funds for their various habits. They were already supporting Carl, Oliver was not going to hire another one. That left him with 8 applicants to choose from.

They all needed the job but his heart kept coming back to the teenage girl who was six months pregnant. She had finished high school and was supposed to go to college but when her parents found out she was pregnant, they kicked her out and refused to help her pay for college. The father of the kid turned his back on her as well. She was staying at a friend's house at the moment but she needed a job to pay for her doctor's visits. No one else would want to employ her as in 3 months time she would need maternity leave, and they would need another employee to fill the void. Her pregnancy would also affect the amount of work she could actually do. Oliver shouldn't have asked her so many questions about her life, it would have made it easier to reject her. He looked back at the other seven but the feeling that he would not only be rejecting her but her unborn child as well, plagued him. Her struggle just reminded him so much of Donna.

At the end of the night, Bob asked him who the new waitress was going to be. He told Bob about the final applicants. He told him he wanted to hire the pregnant girl. Oliver felt it was the right thing to do. Bob's response was simple, "if it's the right thing to do then it's the right thing to do. Call her in tomorrow," And that was how a young Samantha Clayton got her job at Off the Beaten Strip.

Oct- 4

Early the following week, Oliver received a call from Tommy.

"Ollie, I'm in town,"

"What do you mean you're in town?" he asked.

"I'm in Vegas. I know you're here. I want to talk to you face to face," Tommy said seriously.

"How do you know I'm in Vegas?" Oliver asked.

"I cornered your father. He spilled everything to me, once I promised not to tell anyone."

"You actually got him to tell you?"

"Hey I can be persuasive when I want to be."

"Then you know I can't be seen with you. I am going to win this challenge."

"But Ollie,"

"No buts Tommy. I'll be home next month for Thanksgiving. We can hit the town then."

"I really wanted to talk to you face to face about Laurel. I have pestered your father every day since September and its only today that I got the details from him,"

"Why didn't you just ask me where I was?" Oliver asked.

"Give me some credit Ollie, I know you. You would have given me the same bullshit story about Europe. I knew this 'trip' had to do with your father,"

"You were always the smarter one,"

"Yes I am so trust me when I say we should talk,"

"Tommy, I wasn't lying when I told you I was fine. You dating Laurel isn't going to be a problem," Oliver said honestly.

"Then why have I barely heard from you since you found out about Laurel?" Tommy asked.

"Because, I can't afford to talk to you Tommy. It's expensive." Oliver said frustrated. Since he paid all of Felicity's bills he had to cut back on his personal expenses which meant cutting back on his phone bill again.

"Your dad is making you pay your phone bill?" Tommy asked in disbelief.

"Yes," Oliver answered.

"That sucks man,"

"It does suck but since your phone is still paid for, I'll text you my local number here. That way we can talk longer without me getting the roaming charges."

Oct-5

It was October 15th, it was the end of the Sholshim period for Felicity. Oliver had been counting down the 30 day period. He asked Felicity to meet him at the bar. He wanted her to be here for this. The bar had been far too quiet. Oliver walked over to the juke box and turned on Donna's favourite song, I Will Survive, by Gloria Gaynor.

"Come let's dance," he said to her holding out his hand to her. It was the first time the juke box had been turned on.

She raised her eyebrow at him, "I thought you couldn't dance,"

"I never said I couldn't, I just prefer not to," he told her.

"And what's changed your mind now?"

"Guess I haven't heard the juke box in a while and I really missed you on the dance floor," he said motioning with his hand for her to come towards him. It wasn't the best song for formal dancing but he really wanted to hold her.

He couldn't help the smile that formed when she left her stool and came over to him. Her hand slipped into his easily. He rested his hand on her waist and started to rock in time to the song. She followed him. He progressed from the rocking side to side to some more complicated dance steps. His mother had forced dance lessons upon him when he was a teenager so that he could impress at galas. He had hated every moment of it yet there was something entirely different about dancing with Felicity. He had no doubt that she would be able to follow him.

Others joined them on the dance floor and soon there was a steady stream of music from the juke box again.

"Ok, you two lovebirds break it up! Someone is supposed to be working," Bob reminded Oliver.

Both of them blushed furiously as they returned to their previous positions. For the rest of the night, Oliver could still feel a tingle in his left hand where he held Felicity's hand in his. The smell of her shampoo haunted him even as he mixed various drinks.

Oct -6

Oliver made sure to put an extra effort into the breakfast the morning that Felicity decided it was time to go through her mother's wardrobe. She knew she was going to give away most of her mother's tight dresses to the poor since it wasn't exactly her style. Felicity's dresses tended to cover a bit more skin than Donna's did. They did have the same shoe size so Felicity wasn't parting with a single pair. With the exception of a few heirloom pieces, Felicity gave away her mother's jewellery. Most of it was cheap costume stuff that she wore to work at the casino. Felicity didn't want any of those pieces.

At the back of the closet she found her mother's Hanukkah decorations. She mumbled something about making sure she had her presents for Hanukkah and Christmas ready early to avoid the late shopping rush. It was then Oliver realised that he had to purchase Christmas presents for his parents, Thea and Tommy on a bartender's salary. How on earth was he supposed to get something that they would like?

Oct-7

Oliver installed a pull up bar in the corridor that lead down to the bedrooms. As soon as he heard Felicity moving around in her bedroom, he timed his second pull-up to Felicity exiting her bedroom. To make her feel comfortable his back was facing her. She had a great view of his shirtless back as he pulled himself up. He had discovered that he liked to tease her. Her reactions never failed to please him. After his set was finished he jumped down and turned around as if heading to the shower.

"Morning Felicity," he greeted her brightly.

Her face was bright red and her breathing was a bit shallow. When she didn't respond, he walked closer to her, "you ok?" he asked.

There was still no response. He flicked her forehead with his index finger and she snapped out of her trance.

"Oh Oliver, hi, I think I left something in my bedroom," she said turning around and slamming face first into her closed bedroom door. "Ow," she groaned. "I swear all these inanimate objects have just suddenly started attacking me!"

Oliver chuckled before stepping into the bathroom. Perhaps he needed to stop teasing Felicity but the thought of going without seeing the pretty blush that spread across her face was unbearable. Instead he just decided to move the furniture around a bit so that she wouldn't hurt herself.

Oct – 8

Felicity was seated at the bar with her usual glass of wine when an old man came in and sat next to her. He saw Felicity tense up and he was about to head over to her when she shook her head at him not to approach. After a few minutes of conversation, she told Oliver she was heading outside for a few moments and she would be back. She exited the front of the bar with the strange man. Diggle set himself up at the front window where he had a view of the two outside talking.

"I never thought I would see that bastard again," Bob said coming out from the kitchen

Oliver threw a questioning glance over his shoulder at Bob.

"Felicity's father," Bob said to him.

"Oh," Oliver said wondering if she needed him.

Ten minutes later she came back in alone visibly upset. Oliver reached out and took her hand in his, "Whenever you're ready to talk about it, I'm here. You can tell me anything." He gave her hand a gentle squeeze before he returned to duties.

Oct-9

It was a very slow night when Oliver saw a thin man dressed in expensive clothes enter the bar followed by two men who were clearly hired muscle. Diggle had immediately followed them into the bar. Felicity was sitting at the bar babbling away about why kangaroos were scary when the men approached the bar asking for Carl. Oliver wondered if this was Carl's drug dealers. The boy had called in sick two days in a row which was unusual for Carl.

"Felicity why don't you go into the office, I need another bottle of rum," Oliver said to her. The hired muscle was eyeing Felicity like a piece of meat and whatever was about to go down, he didn't want her around.

"But you just took out a bottle yesterday?" Felicity responded clueless.

"Go to the office Felicity," Diggle encouraged her. Even the regular customers had slunk away from the bar.

Bob came through the doors from the kitchen, "Felicity, my computer's been giving me trouble, go and take a look at it and take Alice and Sam with you."

She reluctantly followed Bob's orders grabbing onto to Alice and Sam before disappearing behind the door.

"What can I do for you Anatoly?" Bob asked.

"My dear friend Bob, there is no reason to be so apprehensive. I mean you no harm. Pull out that special bottle of Russian vodka and let's have a drink," Anatoly said with a thick Russian accent.

Bob glanced at Oliver a moment before he headed back to the kitchen returning with a half full bottle of clear liquid. The old man got two glasses filling them.

"As you Americans say, cheers," Anatoly said lifting his glass.

Bob toasted with Anatoly and downed the drink in one go.

"Now that that bullshit is out of the way, what do you want Anatoly?" Bob asked the man.

"You're lucky I like you Bob. I don't appreciate people using such foul language with me. I'm looking for that little rat that you keep employed here, Carl."

"He isn't here. He's out sick."

"He owes me 10k. Tell him I want my money or he might find himself unable to work at the bar again." Anatoly stood up, looked around the bar before walking away with his goons in tow.

"This looks like it's going to be a problem," Diggle commented.

"I'll deal with it. I've handled Anatoly before. Out of his entire bunch, he's honourable. Once he gets his money, he'll back off."

"I doubt Carl has 10K lying around," Oliver pointed out.

"Don't worry about it,"

"Is he gone?" Felicity's voice floated through the slight space in the open door as she peeked out.

"Yeah you can come out now,"

"Good," she said swinging the door open to reveal the double barrel shot gun she had in her hand, Alice and Samantha behind her.

Oliver did a double take when he saw the gun. He didn't know Bob had one.

"Felicity what are you doing with my shot gun?" Bob asked.

"I thought when you sent me in here you wanted me to get it?"

"I sent you in there because I wanted to keep you safe?" Bob responded

"Yeah safe with the shotgun," Felicity responded still holding onto the gun.

"Do you even know how to use that thing?" Diggle asked.

"No, it can't be that hard to figure out," Felicity commented. "Point and shoot?" she shrugged.

"You would have to put shells in it first," Bob commented, "I'm not foolish enough to keep a loaded shotgun lying around,"

"Oh, you'll have to show me where you keep those then,"

"No!" the three men chorused together causing Felicity to frown.

"Is this some male chauvinistic thing because girls can use guns too you know," she replied hotly.

Bob walked up to Felicity, removing the shotgun from her hands, "don't worry about it. Go keep Oliver company, the kid looks like he's going to have a heart attack every time you point the gun in his direction."

"Oh, sorry," Felicity said sheepishly moving over the bar and jumping up on her stool.

Oct- 10

Bob had come around to some of Oliver's plans and allowed him to specially promote the bar for certain occasions. As a result they received a booking to rent Off the Beaten Strip for a Halloween party. The rental fee alone was equivalent to what the bar made in a week. Bob was quite pleased with the development. Felicity was secretly gloating that she had been right about Oliver taking baby steps with Bob. Oliver however thought that Bob had paid off Carl's debt himself and he needed the extra income to replace what he spent.

In keeping with the theme everyone had to dress up in costume. It was going to be a huge party since they had booked the bar for a near capacity crowd. Oliver was concerned about Samantha. She had been doing wonderfully. She was not afraid to work despite her pregnancy. She said she didn't want any special treatment but that didn't stop any of them from helping her out. Even Carl pitched in to help her carry the heavier trays. It was going to be a lot for her so Oliver asked Felicity to help him with the bar so he would be free to dart out to the tables with some of the larger orders.

At first Oliver did not know what he wanted to dress up as. It was after staring at Felicity's Robin Hood poster on the wall that it occurred to him he could go as a modern day Robin Hood and Felicity could be his Maid Marian. He sent a quick text to Tommy to fedex him his green leather pants from the Manor. He was not wearing tights! If Tommy could manage to find it, there would also be a bow and arrow stored somewhere from Thea's archery classes at school. He just needed to source a shirt to complete his outfit. Felicity loved the idea and they went shopping together to put their costumes together.

The night of the party, Alice was dressed as a witch, Bob dressed as Frankenstien, Carl as something called an Orc from some game and Samantha settled on a Greek goddess dressed in white robes. The party was as busy as he expected but he didn't expect the anger that surged through him every time a particular vampire went to Felicity for drinks going as far as to ask if he could do shots off her neck. He was even angrier when Felicity smiled at him and politely told him no. The next shot the vampire ordered, Oliver made sure he added Tabasco to it when Felicity was distracted by another customer. The surge of pleasure he felt as the man gasped when the Tabasco burnt his throat was wonderful. Felicity however was not happy when she figured out what he did. He was subjected to her loud voice for the rest of the night but it was worth it because the Vampire didn't come around again.

He was half way through the challenge but he was too angry to even realise. Thoughts of Felicity and the vampire were plaguing his mind.