Chapter 5 – Always bet on Felicity

AN – Really appreciate all the love for Roy and the Lessons! This chapter follows up on the gala and betting mentioned in past chapters so I wanted to sneak it in before tonight's episode! Fair warning – my beta (Mic Riddy) had the day off so all mistakes are certainly mine but I do hope you all and Mic enjoy this anyway! Oh and for those that read Team Arrow Training Academy (thank you btw), I'm sticking to the "one-shot" thing but I may work Barry back in here! :)

DISCLAIMER – Insert standard legal jargon here as nothing belongs to me!

"Ok, so to be precise – the bet is whether or not Oliver will sneak away with one of the…how many girls, um, chances do you get?" Roy and Thea were grabbing a bite to eat at the bar at Verdant before the evening's event.

"I don't know but at least three…I won't really know until we get there and I see the choices though." Thea's hedging had Roy narrowing his eyes.

"You can't get unlimited chances – well, hmm, that would probably help me though because eventually your brother will figure it out and get angry." Roy couldn't resist taunting Thea and wasn't surprised when she immediately responded.

"Fine – the bet is that he'll sneak off with one of the…five girls I introduce him to tonight. Winner gets to name the stakes as usual?"

Roy noticed Thea's smirk and knew she was confident of her victory as she knew pre-Island Ollie would certainly have gone after at least one (or two) of the available girls. Roy didn't bother to suppress his own smirk though as he knew a few things about Oliver after the Island: 1) Never get between Oliver and Felicity and 2) Never bet against Felicity. He offered his hand which Thea quickly shook even if her smirk had become a bit more of a glare.

"And why do you feel the need to set your brother up anyway?" Roy was genuinely curious about Thea's motivation. Ignoring Lesson #1 completely, he couldn't see where Oliver would even have time for anyone new in his life. Of course, Thea didn't know that but still…

"He doesn't laugh anymore."

Roy was surprised by Thea's quiet comment and looked up to see her head was bowed and she stared at her hands as she fidgeted nervously. He really thought this was just a game to her so this wasn't what he expected. He was even more surprised as she continued without meeting his eyes.

"You didn't know him before the island but he was always laughing, easy going, fun – always in trouble, I know, but still he was happy. I get that he can't be that person anymore but I think he deserves to at least smile again and not that fake smile he does now but a real smile." Thea finally looked up and met his eyes.

Roy smiled, nodded his agreement and then leaned in for a sweet kiss before he teased her. "My own Rich Girl with a heart of gold." As Thea pretended to glare at him Roy again kissed her but with more heat than sweetness this time.

The rest of the afternoon flew by as Roy worked at Verdant and ran a quick errand for the Team as they needed a little information from one of Sin's sources. It was now close to the fundraiser start time and Roy knew better than to be late. Thea planned to arrive early to ensure a smooth night and Roy intended to be there with her. He quickly got ready and even made it to the hotel just minutes before Thea arrived.

Upon first sight, Thea still looked like the 'Rich Girl' he teased her about being but he had come to realize she had a public face just as the Team did. He watched as she greeted the doorman and then the hotel employees who rushed to her. Despite her calm, confident mask, Roy could see the nerves underneath and he stepped forward so she would notice him. She immediately smiled as she headed his way and Roy couldn't help but smile back. Despite enjoying the Team and being glad he had that reason to live, Thea is what made it worth it and made it fun. Roy ran his eyes over her slim body and enjoyed how the metallic dress clung tightly but still looked…classy. That was the word to describe Thea whether she was in jeans or a dress – she oozed sophistication and class. It usually made Roy slightly uncomfortable when she was in the fine clothes and being the Rich Girl but tonight he simply felt proud of her. Clearly the 'supportive boyfriend' thing was the easiest Lesson yet.

He was surprised when she hugged and kissed him but he realized then he wasn't wrong about the nerves and Thea must need his support. He held her tightly when she tried to pull away and whispered softly, "Go get 'em Rich Girl." He felt more than heard her laughter and smiled himself. He also noted she seemed more relaxed now as she turned back to the staff and proceeded to command her troops as any good general would.

Roy stayed close to Thea but didn't interfere as she continued her work even if she didn't look like she was working. The time passed surprisingly quickly and soon there was quite a crowd of people milling about the room as guests and the press had arrived. Thea continued to work tirelessly and Roy continued to keep her in his sights as the event really got going. He was watching Thea float from group to group charming everyone when he saw Oliver out of the corner of his eye and turned to watch him instead.

Roy smiled when he saw Oliver walk in alone as he had wondered who would actually win last night's 'discussion' and clearly it was Felicity. He watched as Thea pounced on Oliver and he hugged her affectionately even as his eyes continued to scan the room. Roy paused then and realized he hadn't been in training mode since getting here as Thea (and her dress) had actually completely distracted him. As he met Oliver's eyes he gave a slight nod and took a deep breath. Head in the game Harper. Roy didn't even think about the fact that those were often Oliver's words to him, he just knew he had to be alert and not get too wrapped up in being just his 'public persona'.

Roy now scanned the room for more details – he couldn't pick up on everything as Oliver and Diggle could but he knew to look for things that stood out. He focused first on the staff as that was an easy access point for anyone wanting entry on the down low. The hotel staff was similarly attired and no one appeared conspicuous – he even checked their shoes as Diggle had taught him they would often be a giveaway as people usually stole uniforms but wore their own shoes. He moved on to the hotel security stationed at each door but again no one caught his eye. Realizing he hadn't located the possible exit or entry points he scanned the ballroom before walking back into the hotel lobby to search possible paths there too. He wasn't surprised to see Diggle out there as he appeared to be making his own evaluation…of course, Roy noted he was doing it when he entered and not several minutes later. Roy gritted his teeth and remembered the Lesson about only getting one chance to make and take that first impression of anyone or any situation. Whoa, talk about first impressions!

Roy was distracted again but this time by Felicity. She entered the hotel at that moment and immediately smiled at him before moving toward Diggle. She looks good, Roy thought even as he realized that would also go on the list of things not to say in front of Oliver. He might not know anything about fashion but Felicity's dress fit her body well and the bright blue drew attention as did the slit along the side. He quickly crossed the room to join them before realizing he wasn't sure if it was appropriate – he still didn't quite understand that whole public persona thing and he wasn't used to basically ignoring his friends just because others were around. Roy was still standing undecided in the middle of the lobby when Thea called his name. Giving a quick nod in the general direction of Diggle and Felicity, he turned to move toward Thea instead.

"Ollie's here so come and say hi to him and Mom. After that, you have to stick around as you'll have to dance with me...just once, ok? I know this isn't your thing but I'm glad you are here Roy!"

Thea clung to his arm and smiled at him even as she dragged him toward her family. Roy knew it was sappy but he couldn't help thinking he would do anything for her, anything to keep her safe and anything to keep her with him.

"Roy."

It was Oliver's voice that startled him out of his thoughts on Thea. Roy was pretty sure he was the only one who understood the tension behind the Oliver's expression and tone. Hoping he wasn't channeling Felicity and actually blushing, Roy was still embarrassed that Oliver knew he had been so thoroughly distracted for the second time that night. He then noticed Oliver's hand and quickly shook it. That gesture helped him focus and the nod from Oliver was actually encouraging (at least it was in Oliver speak as Felicity would say).

"Oliver. Mrs. Queen. It's good to see you both." The words felt stilted and foreign to Roy but he pushed them out as wanted to support Thea and he didn't want to disappoint the Team…and if that meant suffering through a superficial society shindig with Thea's family then he would just have to suck it up.

"Thank you for coming, Roy. The whole family appreciates your support."

It was Moira Queen who made that comment even as she looked over his shoulder. Roy barely suppressed the urge to turn around when she continued to speak.

"Oliver, isn't that your secretary?"

Even though it was ok to turn around now Roy kept his attention on Oliver as he wanted to see the man's reaction to Felicity - he was kinda disappointed as there was only a slight flicker in Oliver's eyes as he looked at the blond. Roy couldn't help but be impressed at just how good the Team was at handling their public personas while he had only realized this Lesson wasn't as easy as he had thought.

"Hm, it is Felicity – I'll be right back. I just need to have a quick word with her about a meeting tomorrow." Oliver's words were just as bland as his tone but Roy did notice he hadn't taken his eyes off Felicity yet.

"Ollie, come back quickly. There are some people you need to meet!" Thea admonished.

Roy almost rolled his eyes as he knew that 'people' meant attractive brunettes as Thea still believed that was his preference but instead he just remained silent and stepped slightly to the side allowing Oliver to pass. Roy turned a bit and put his back to the wall so he could now scan the ballroom while keeping an eye on Oliver and Felicity.

Even though he was looking for it, there were no signs of inappropriate closeness between the two which again disappointed Roy. Thea had mentioned the rumors at QC previously and also how often the pair were together but Roy knew she didn't really suspect anything and he could understand why now. Oliver and Felicity both seemed to keep a respectable distance but as he watched them throughout the night Roy did see each of them take a step back once or twice as if just remembering their 'public personas'. Roy again realized just how much more complicated this whole Team Arrow thing was as he was forced to watch his friends from a distance. He noted they often made eye contact with each other and even him. There were even a few subtle hand gestures but rarely were there any other interactions between the group. He couldn't imagine anyone else watching would be able to link them together. He tried to model his own behavior on theirs – might as well consider this training too.

When Roy saw Felicity alone at the bar he saw his opportunity to at least chat with her and casually but quickly made his way over. Standing close enough to hear one another but not so close as to draw attention Roy spoke quietly.

"Ok, clearly the 'girl time' worked for you as you look great Felicity!"

He wasn't surprised to see her slight jerk at his voice nor was he surprised to see her blush. She truly didn't seem to realize how beautiful she was and Roy felt safe thinking that as he really did consider her a sister, he loved Thea and he knew Lesson #1 by heart now as he valued his life. He decided to continue before Felicity could start rambling about her 'girl time' though.

"You may be interested in knowing Thea and I have a bet going tonight…and I'm going to win because of you." Roy continued resist teasing Felicity as she was already blushing

"What?" Felicity turned and stepped toward him so Roy followed her lead and assumed it was safe for them to speak briefly.

"Thea is going to parade a series of brunettes in front of Oliver tonight and she bet me that he would sneak away with one before the event was over." Roy couldn't help smirking as he thought about just what stakes he would name as victor.

"Roy? You'd better be kidding! I think that would be considered insider information and should disqualify you!" Felicity smiled before frowning thoughtfully. "Plus you don't know for sure Oliver won't find a brunette to…" Felicity trailed off uncertainly as if unwilling to make her own point.

"Nope, I'm betting on you and Lesson #1 Felicity – it's a sure thing Oliver won't be sneaking off with a brunette tonight! Thea's gonna owe me big time!" Roy couldn't believe Felicity still didn't see Lesson #1 as he did but as that meant he got to tease her and win a bet against Thea he was ok with it.

"Ok, you two – break it up." Diggle had appeared suddenly and startled both of them.

Roy tried to smooth out his glare but he was really looking forward to the day when neither Diggle nor Oliver could sneak up on him anymore. With that thought in mind, Roy turned just in time to see Oliver himself join them.

"Is there a team meeting I'm not aware of?" Oliver asked as he moved close to Felicity to order a drink.

"Aha! You said Team. Admit it, the name works for us." Felicity laughed as she teased Oliver and even put a hand on his arm. Roy watched as Oliver smiled at her and before he shook his head. He then just stared at her and remained silent – Roy knew he wouldn't acknowledge their 'Team' name but it looked like they were both willing to wait the other out as they continued to stare. Roy was just about to interrupt them when Felicity moved quickly back and dropped her eyes.

"We really need to quit meeting like this guys. Don't we all have jobs to do? Roy, maybe its time to be the supportive boyfriend and dance with your girlfriend." Diggle redirected the group focus and each moved off to do his or her own thing. Roy watched Felicity blush even though she looked to Oliver once more before she moved away.

The rest of the night was uneventful for Roy and he remained mostly along the edges of the ballroom. He did dance with Thea as Diggle had taunted and even though he enjoyed holding her close, it was also a distraction he couldn't afford. He had felt the Team's eyes on him both times he danced with her and he had tried to push himself to notice more than just Thea but it was surprisingly hard. He met Felicity's eyes and saw her smiling nod but he also knew she was thinking more about his and Thea's relationship than about safety or training. He chose not to meet Oliver's eyes as he knew he was still thinking as Thea's protective older brother as well as the Arrow who trained him.

Roy was again standing off to the side as he watched Felicity and Oliver finish their own dance and go their separate ways. He just couldn't find fault with their public personas and knew no one else watching would bet on them as he would. And speaking of bets, Roy watched as Thea made her way to him. Out of the corner of his eye, he also saw Felicity escape onto a balcony.

"Roy, you need to come with me as I'm about to win the bet!" Thea practically bounced on her toes as she made that gleeful announcement to Roy. "Ollie just ditched Mr. and Mrs. Williams and headed out to the end balcony!"

"Really? Well, lead the way and let's see who wins!" Roy could barely suppress his smirk as he had realized that was the same balcony Felicity had gone to as well.

Roy ignored Thea's taunting about being unable to decide between a full body massage or risking her life to make him cook for her. He was trying to listen for Oliver and Felicity as while he knew they weren't interrupting as Thea thought (at least he hoped they weren't) he was concerned with what had required the pair to meet. When he heard Felicity's playful laugh as well as Oliver's low chuckle he turned to Thea and saw her expression of smug satisfaction.

"Told ya – he still can't resist a pretty brunette! Get ready to pay up Harper!"

Roy just shook his head as Thea pushed through the doors and immediately started her fake apology for interrupting before she froze. Roy came around her to stand by her side and saw that Oliver and Felicity were a couple feet apart though he was willing to bet they hadn't started that way.

"Well, hello you two – so sorry we interrupted. Aren't we, Thea?" Roy could barely contain his laugh especially when he noticed Felicity was blushing and knew she remembered their earlier conversation. As he watched her she opened her mouth to begin what would probably be a rambling defense but Oliver stepped close and pulled her by the arm to move past Thea as he spoke.

"Sorry Thea – work emergency. We've gotta go. Tell Mom good night for me and congratulations on this. It was a great night." Oliver continued to walk as he spoke so the last part was tossed over his shoulder as he pushed Felicity through the doors and back into the ballroom.

Roy watched them go before he turned to smile at Thea. "Hmmm, what were you saying about a full body massage and home cooked meal Ms. Queen?"

Thea glared for a moment before grumbling, "I really thought someone would catch his attention. I can't believe he's just so focused on QC work that his secretary is never more than five feet away!" Roy watched as Thea continued to glare at her brother's back. "You know, she got to Verdant right after he did that night Laurel was drunk and that was certainly after work hours. You don't think they are…" Thea trailed off as she gestured.

"No idea, Thea, but I don't think its any of our business…just focus your energy on paying off your debt to me!" Roy glanced around quickly for witnesses before leaning over to kiss the frown from Thea's lips.

Lesson #1 is finally paying off! Roy thought with a laugh as he again brushed his mouth against Thea's and felt her arms sneak around his neck.

AN2 –Pls keep your ideas and suggestions coming – I especially need the Lessons you want Roy to learn! And yes, Oliver will eventually have to hear Lesson #1 but I'm putting that off until I see where the show goes w/ this story line! Thanks for reading!