Summer of Olicity Challenge

Prompt: Felicity becomes friends with Tommy, Oliver gets jealous when he thinks there's something more between them

Okay so well, I finish Chapter 4 for my story, I got a little idea of what a conversation between Tommy and Felicity would go like and then I saw the Challenge on tumblr and thought it was a perfect opportunity to put down that idea on paper. So here is my little one-shot. It will not be continued but it might be added to my story in future in some way if it fits once we hit that point. Hope you enjoy it, Please review!


"One, two, three go!" shouted Tommy.

"Ahhh haaaa I won, I won IN YOUR FACE, Wizard" said Felicity jumping off the bar and literally running circles around Tommy.

"Seriously Smokey, you need to come up with a better name than Merlin the wizard"

"Once you come up with a better one than Smokey the Bear"

"Ohh come on, my catchphrase is fantastic 'only you can prevent crime, with cyber-crime of course but that is beside the point' see perfect" responded Tommy with his best charm filled grin.

"Wizard" Felicity simply repeated over and over.

"Ugghh come on you are killing me here, I would take Merlin the Great, or Tommy the Tiger, YES! I like that because I am definitely a tiger in every aspect" Tommy winked at Felicity.

"You want to be named after a kid's cereal character? I guess that fits cheesy, childish, and artificial sweetness, yeah I can do that"

"Ha Ha very funny, you know damn well what I meant, but if you have doubts I am more than happy to give you a demonstration anytime you want maybe we can give new meaning to Smokey" he looked at her with a smirk and a mischievous twinkle in his eye.

She narrowed her eyes at him and sternly said "or I could give you a demonstration of my cyber-crime skills and O-B-L-I-T-E-R-A-T-E you" she smirked

Tommy raised his hands in surrender while semi honestly responding "whoa take it easy, I said nothing, the wizard gives up"

From a distance they hear a frustrated Oliver shouting.

"Felicity! Felicity are you up here, damn it where did you go?"

"Oh nooo the Hood" He says sarcastically and with a bit of disdain "is looking for you, you are iiin trooouuubleee"

"Tommy" She says with a bit of sadness and hurt "please…"

He interrupts her and just looks down and whispers a low but very sincere "Sorry City".

She half smiles and nods before darting behind the bar just as soon as Oliver comes around.

Tommy suppresses a laugh and gets very serious as soon as he sees Oliver.

"She's not here"

"Tommy, I didn't know you were here, I was just looking"

"I know who you are looking for. Need your personal IT girl to help you kill someone else", he spat out.

"Tommy, look…"

"Save it. For her sake I hope she got some sense and finally left for good" he told him as he turned around towards the office, shooting felicity a sympathetic and somewhat apologetic smile. He hated that Oliver still had that effect on him after so many conversations with Felicity. He figured it was a plus that after every time he was so dismissive he was also beginning to feel guilty and angry about his reactions, and Felicity also noticed and took it as a win.

Once he was gone Oliver walked towards the bar having noticed tommy's gesture and very calmly said "You can come out from behind there Felicity"

She winced at his knowing tone and slowly but carefully peeked up from the bar until she was fully standing in front of a no nonsense Oliver. She swallowed hard and braced for whatever was coming…


A week after Tommy found out about Oliver's secret identity his inability to process and accept the information was becoming soul crushingly unbearable so that is how on a Monday at 1pm he found himself at Verdant drinking alone replaying the past almost 30 years of friendship. It was hard to accept that this was the same best friend he had experienced every important first in his life with. Now as he threw back his third glass of 15yr old scotch and looked over the brim of the glass he saw a precocious and hesitant blonde approach him. He had seen her before, the IT girl, who seemed to spend a lot of time setting up the internet router, now the question was, why was she walking directly towards him?

"uhmm hello Mr. Merlyn" she said hesitantly and hopeful that she was doing the right thing, but how could she do nothing.

"Hi" he coldly responded

"Felicity Smoak, uhmm my name is felicity Smoak"

He nods and says "Oliver isn't here"

"Yes, I know that's why I am here now, to speak with you not Oliver, I came now cause I knew he wasn't here if he knew I was here talking to you well I don't even want to think about that. Can I sit down?" she blurted out until she had no breath left and then deeply inhaled hoping to gain some control and courage.

Tommy stared at her for what seemed like an eternity until his curiosity and frankly her face full of desperation won over and nodded towards the empty stool next to him. She slightly smiled, which for some reason helped him relax, and she settled in for what she knew would be a difficult conversation.

After more than 3 hours of arguing, explanations and some yelling from Tommy that almost made her smile because it reminded her so much of Oliver they finally sat in silence. She knew she had not convinced him to forgive or accept Oliver but she had managed to convince him that he couldn't abandon a lifetime of friendship. She even managed to convince him to stick around and keep managing the club and almost had him convinced to join her in her crusade of helping Oliver stay grounded, she managed that one by assuring him over and over that he no longer killed people, he had managed to control himself and face the reality that he was not and did not need to be a murderer. He was a man doing right by a city that his family helped destroyed. Although his methodology had started off on the wrong side of either of their moral compasses he had to admit that he had noticed the change both in the news and in his willingness to give him space and not press him. Something told him that had a lot to do with Felicity.

He didn't trust Oliver, but something told him he could trust Felicity, if a simple smile from her could help him relax and one conversation could help him rethink his current relationship with Oliver, he had faith that day after day of her adorable rambling and unyielding will could truly change Oliver.

"So, do you make it a habit to corner people and talk their ear off until they yield and give in" he asked amused.

"Only when they are being stubborn and can't see past their own nose" she proudly responded.

He let out a full hearty laugh and then said "Oh really, such bluntness and sass from the girl that a couple of hours ago almost passed out cause she forgot to breath between sentences"

"I do not know of whom you speak Mr. Merlyn"

"I see why he likes having you around, I mean besides the obvious and the hacking skills."

Felicity seemed to miss that second part or blatantly ignored it not wanting to ask for clarification. Instead she she went with comic relief her favorite awkwardness filler.

"Oh do not ever doubt that I have mad skills" she said with a free laugh that filled the entire club

He smiled and for the first time felt like maybe his life wasn't as broken as he thought. It also helped that he knew he had gained a friend and an ally in Felicity Smoak. Although he was sure her loyalties lied deeper with Oliver he didn't mind. Something told him her deepest loyalty was to her conscious.

For the next couple of weeks it had become routine for them to hang out at the club before hours and she had slowly also made it routine to substitute his usual scotch for lunch or water. He had noticed but didn't say anything he liked knowing that she cared enough.

They had quickly become friends and learned to confide in each other, they would talk about his relationship or rather lack thereof with his father his relationship with Laurel, her relationship with her family and her completely and utterly lacking love life and most of all they complained to each other about Oliver. It was unexpected but their older brother little sister relationship had really helped them both and gave them a much needed escape from the turmoil and craziness that had taken over their lives.

They had even wandered out of Verdant and hung out like real friends, nicknames and all.


"Felicity, what were you talking with Tommy about?" Oliver asked a bit more accusatory.

"I wasn't" She said unconvincingly "I just happened to bump into him when I came up"

"So why were you hiding"

"I wasn't!"

"Felicity" he said his patience wavering

"Okay, we chatted a bit nothing serious just small talk, Look I know you guys are on shaky ground and I didn't want you to feel like I was taking sides that's why I lied, I'm sorry but it was just small talk that's it"

He looked a bit ashamed for causing her to get so flustered over something that was his personal issues so he simply nodded and informed her that the computers were dinging.


The next time he "caught" them talking, he had been taken so aback by their conversation that his reaction was to simply walk away, of course angry, confused and something that felt and tasted a lot like jealousy but, silent nonetheless.

Like had become customary while Oliver was on patrol and Felicity was running diagnostics she would come up to Tommy's office and they would share a couple of drinks and her latest dating horror story and his collection of best one liners from the bevy of women that threw themselves at him. This night as they sat in complete uncontrollable laughter like children Oliver made his way back to club after deciding to end patrol early, it seemed the Hood was beginning to have a noticeable effect on late night crime in the glades.

"OMG, Tommy she did not tell you that!"

"Oh yes she did, no shame, I tell you I have no idea how it was that I used to live for women and situations like this before, they are utterly ridiculous"

"I really didn't think women said things like that to men they didn't know, I mean you could be a sadistic asshole"

"HEY, Smokey! What the hell?!"

"I said could be, relax you're not sadistic"


"And what?" she asked innocently

"Ohhh so that's how it is am an asshole?"

"You said it not me, wizard"

They both began to laughed boisterously

"Okay, okay but, you have to give me more. How did this go down, details dude"

"I have a better idea you be her and I'll be me and you'll see exactly what happened because we are in the scene of the crime"

"Ohhh role play, I love this, visuals make everything so much better"

"Now you stand by the door while am sitting at my desk going over some paperwork…" as Tommy continued to explain and set it all up they both laughed and giggled like school girls. Tommy more at how badly Felicity blushed and how even worst, she was at playing the seductress. He teased her mercilessly until she got that devious look of "challenge accepted" in her eyes.

As Oliver made his way up the stairs ready to play the playboy persona and make his club rounds he heard familiar voices from Tommy's office as he made his way over he couldn't believe what he saw and heard.

As Tommy sat in his chair Felicity stood by the door she let her hair down and with a sway of her hips made her way over to the desk, she walked around it and then hoped to sit on it and crossed her legs slowly and with devious meaning. Tommy shocked just stared up at her until he saw her smirk and then realized the game she was playing and he would be damned if she was going to win so he played along and smirked right back ghosting his hand on her knee. She almost gave in but, instead she straightened her shoulders and continued.

"Tommy Merlyn" she purred, his name came off her tongue like velvet that he would be lying if it didn't give him a bit of a chill.

"I've been coming around for weeks, stealing glances and touches and not once did you have the courtesy to invite into your office, tsk tsk tsk, Mr. Merlyn, manners"

"Forgive me for being…"

"Shhhh" she says putting a finger over his lips while bending forward. She trails that same fingers across his lips, down his jaw and neck to finally rest on his tie and slowly wraps her fingers around the purple silk. Then she slowly wraps her hand with a twist of the wrist and roughly tugs him forward as she leans closer. She licks her lips and without missing a beat in her most breathy, demanding voice she tells him

"Anything, Anywhere, Anytime"

Oliver had had enough and quickly made his way to the foundry before he beat Tommy and picked up felicity and dragged her down to the foundry where she belonged, with him, he meant helping him...them...the hood.

As Tommy and Felicity sat only inches away she slowly deadpan

"I see you went with the animal style on your In-n-Out Burger"

He blows a deliberate breath out and says "wouldn't have it any other way"

She lets go of him with an audible "Ewwwwww Tommy"

As he jumps out of his seat and shouts "I win, take that Smokey. Asshole 1 seductress 0"

They both laugh so loud they drown out the music. When her tablet dings letting her know that the computers are done, they say their goodbyes and make plans for next time as she heads back to the foundry. As she settles in her space she hears noise in the darkened corner of the basement.

She lets out a shaky hello.

"Where were you?" a calm yet somewhat menacing voice echoes from the dark.

"Jesus, Oliver! You're back early"


"Uhmm" he doesn't even let her answer before repeating his question.

"Where were you?"

"I…I was just taking a break. Went upstairs to grab a drink help me clear my head a bit."


"Why? Did you need something, did something happen on patrol"

"No I don't need anything, absolutely nothing" especially from you he mutters under his breath as he makes his way back upstairs. She is left a bit confused like she walked in to this half way through the conversation and missed the entire point and the reason for his mood. As Oliver runs into Tommy upstairs he can't help but notice the amused smile on his face and for maybe the first time in their entire friendship he knows the reason for the smile and he wants to punch it off his face.


The third time he "caught" them talking was shortly after the second, lying was out of the question, it was blatantly obvious that they were having a grand ole time in each other's company and more importantly talking about him. He watched as they talked to each other with such familiarity and something boiled deep inside him. He had been attentively watching them trying to decipher more from the night he caught them in his office but things were getting so complicated for the hood and dangerous for the Glades that he had almost let it rest for now until the dreaded third and final time.

He was walking back to Verdant after having lunch with Thea and dropping her off at CNRI when he saw them walking and eating ice cream. They seemed to be enjoying themselves and were oblivious to Oliver's gawking. As he got closer to listen to their conversation as they sat on a park bench, he heard as Felicity told him about the case with Roy, Thea's friend, and how demanding and harsh Oliver had been with her, but before she could tell him about his genuine friendly gesture and right after Tommy's well intentioned jab at Oliver he walked up right beside them and cleared his throat taking them out of what they thought was a private conversation. They both quickly scrambled to their feet to find an irate Oliver who simply spat out

"Verdant, NOW!" through clenched teeth

They both unconsciously nodded like teenagers caught by their parents and simply walked in silence back to verdant to find a stoic Oliver standing by the bar.

Felicity wanted to rush to explain but Tommy simply grabbed her hand and nodded, knowing it was best to let Oliver say his peace before, then he would be the one speaking for the both of them. His gesture didn't go unnoticed as Oliver's eyes darted to their hands, Felicity was too busy gnawing off her bottom lip to notice, but Tommy, Tommy on the other hand noticed and internally smirked, he knew he now had the upper hand.

Oliver simply looked at them and said "How long?"

Felicity not even registering the question kept her head down, Tommy simply said "a couple of months"

Oliver nodded and continued, "Does Laurel Know?"

"Does it matter?" Tommy knew he was avoiding the actual questions that were burning him. He was never one to let a sleeping bear be so he opted to poke him with a big stick.

"Why don't you ask what you really want to know? We both know Laurel isn't the issue. The only issue here is Felicity."

At the sound of her name Felicity finally looked up only to find herself caught in Oliver's heated gaze, she saw the anger and betrayal but there was something else that she couldn't decipher.

"You're angry not because of what I was doing but because it was with Felicity, admit it, hood boy"

She had no idea what was happening. What was Tommy talking about? Why was he instigating Oliver? It was then that she noticed they were holding hands, the implication of his words and Oliver on the brink. She quickly jumped away from Tommy nodding her head and repeating no.

"Are you both crazy, we are just friends nothing else" she said almost shouting.

She could see Oliver wasn't buying it and Tommy not to be derailed walked towards her put both hands on her shoulders and leaned in to whisper in her ear.

"Trust me City, I know what am doing, if I am right, and I am, this might be the solution you always needed. Let me talk, you just go along" he pulled up to meet her eyes and with a soft and honest smile simply repeated "trust me City".

Dammit if she didn't truly trust him. So, she took a deep breath and braced herself for the ride.

"Oliver, am still waiting for you to deny it" Tommy said without losing a beat as he turned back around to look at him.

He was still recovering from their little display and the ease with which he controlled her nerves and rambling.

"Are you serious? You're not even going to try and explain, deny it or clarify?" he said incredulously.

"We know when we are beat" Tommy said holding her closer to him.

"Ohh" he said with a cynical chuckle "it's WE now, I see" Tommy simply nodded as Oliver continued.

Tommy's cynicism was wearing his patience thin, and Felicity's silence and the way she just clung to Tommy was making knots in his stomach and giving him heartburn, it had to be heartburn because the alternative was far worst.

"I'd frankly expect anything from you Tommy, why would you respect boundaries. But you Felicity, I expected more I expected everything from you. You impose your moral high ground at every turn but look at you, look where you stand now"

That hurt, Tommy could see it and was beginning to regret this plan. Oliver could see it too and it was giving him more...heartburn. Tommy was to far down stream to turn around now so he pressed on.

"Look Oliver you can speak to me like that, but not Felicity. Besides what does she owe you that you would so arrogantly expect everything from her? She doesn't belong to you, she works for you and what she does on her time is her business. I'm starting to think it's not about Felicity being with me it's about her being with anybody."

At that last unexpected statement Felicity realized what Tommy was doing and implying and quickly let go of him and moved between them as she noticed that they had been getting dangerously closer.

"Stop, just stop right there" she said in her loud voice extending her arms out a hand directly over each of their chests.

"Come on admit it! She's right there"

"Shut up" growled out Oliver

"What? You want to fight me for Felicity?"

Oliver took a step forward only to end up with Felicity's firm palm planted on his chest.

"That's it this is over. Tommy, shut up. Oliver you are not fighting anyone, understood" now it was her turn to be angry.

With a lot let less mocking and in the most sincere tone he had used with Oliver since he found out his secret Tommy simply said "Tell her"

Oliver's anger almost didn't let him pick up on the fact that for the first time that sounded like his best friend Tommy, no anger, no resentment, no judgment, just also noticed it and looked up expectantly at Oliver. From across the club they heard an all to familiar yet, friendly and reassuring voice echo Tommy's sentiment.

"Yeah man, tell her" repeated Diggle.

All three turned and looked at him as he just simply walked towards them and with reassuring eyes nodded at a stubborn Oliver and with one look let Felicity know that he was here in case things got out of hand. They all turned back to Oliver, waiting.

"Tell… tell her, what?" He said with zero conviction.

Both Tommy and Diggle both let out a frustrated sigh throwing their arms in the air and simultaneously said "come on, man"

Tommy simply squeezed her shoulder and said "Sorry Smokey" while planting a gentle kiss on her cheek. She felt Oliver's muscles tense under her hand and she was beginning to wonder why, too. Tommy nodded to Diggle towards the bar and they both walked knowing they needed a drink. Oliver and Felicity just stared at them confused. She still had her hand on his chest and he seemed to have leaned a bit more into her touch. While pouring two drinks as an afterthought Tommy said,

"By the way we are just friends, nothing ever happened"

Before Oliver could challenge him, he waved his hand dismissively in the air and repeated,


Then gave him a knowing look. A look Oliver knew well, a lifetime of friendship allowed them to move past words and simply understand each other and recognize that this was honest Tommy, and he never lied.

But he still had questions, what about what he saw in the office? That didn't look like nothing. If it was nothing, why would Felicity hide it why not just tell him? The clink of glasses and Tommy calling them over took him out of his reverie to realize he had unashamedly been staring at Felicity and that soft small hand on his chest was breaking down layer after layer of his defenses. It took all his control to pull away from her touch rather than walking forward and wrapping those hands around his neck, as his snaked their way around her waist. He knew she wasn't ready so he painstakingly pulled away. It took Felicity a couple of seconds to put her hand down as she watched all of them at the bar taking a drink.

She couldn't believe it, they were all there fine and dandy like they've gotten all the answers they needed, but her, her on the other hand was utterly confused, had more questions than before and was now being ignored and she was pissed.

"What the hell? Are you fucken kidding me right now? What was all of this, what just happened? One minute you are going to kill each other the next you are best buds sitting at the bar having a drink? Is this body snatchers,are we in the twilight zone? You are all going to drive me crazy, am losing it. What should he tell me? You're sorry about what? How does Diggle know but I don't?"

They all stared at her with smiles tugging at their lips Tommy simply said

"Language Smokey" under his breath and Diggle fought back a laugh that turned into a snort.

Felicity exasperated with all of them simply turned around and walked towards the door to the Tommy called out

"Come on Smokey, where are you going?"

She simply shouted back "Fuck you all!" and she meant it.

Oliver chocked back on his drink as Tommy said,

"Well, that was uncalled for" as they all laughed. She heard them and wished she could slam the foundry door to make a point but she would settle for another form of payback.

As the laughter died out they all passed knowing looks amongst them and finally Diggle nodded at Tommy and Oliver knew exactly what was coming. Before Diggle could even open his mouth Oliver raised a hand and gave him a look, he was about to do the same to Tommy when he raised an eyebrow and said,

"Oh no, I might also be on your payroll but remember I don't depend on it. What happened? That was your opportunity and you blew it, I have never seen you buckle under that pressure. How has being the hood made you soft at everything else?"

"I am not soft, Tommy, I am cautious and everything else…well…"

"He thinks he doesn't have time for everything else, he was alone on the island and if it cost him everyone he knows, which it will" Diggle interrupts him, leaning towards Oliver and in a preachy tone, "then so be it he will be alone here too, isn't that right?"

"As one of those friends that this new persona almost cost you, let me tell you it isn't just you who had to deal with losing a friend, I also lost my best friend, my brother, and it almost broke me. You're not alone anymore Oliver, what you do affects those around you that care about you, that love you" he says the last bit with a knowing nod towards the foundry.

"Almost? Does that mean that we" he says hesitantly

"Look, I am not saying that we are back to normal, and honestly I don't want to go back." Oliver narrows his eyes and looks confused at him urging him to elaborate.

"I want to start all over, I want to get to know the new Oliver I want to understand the real Oliver. There are parts of you that I don't already agree with but I figured that if someone as kind and amazing as Felicity could look past, all this, then there must be something worth looking for."

"Felicity made you see that?" he said softly not sure he deserved the gesture.

"That's the only reason she started talking to me in the first place…" He told him all about their first conversation and how their friendship grew, in hopes of not only making him understand but maybe making him see that he had nothing to fear, he needed to open up to her, she was the right person and she wanted to be there for him in every way whether she realized it yet, or not. Diggle simply said,

"Sounds about right, that's our good ol' Felicity, that girl sure is something"

"Magical" finished Oliver.

"But, she's not ready is she?" asked Tommy

Oliver simply nodded no with a sad look on his face. Diggle broke in with his usual wisdom.

"She hasn't admitted it to herself, but she is right there with you man. She will realize it soon enough but you have to accept that it might require you stepping up and taking a leap of faith to make her see what we all see."

Oliver smiled up at him as Tommy added,

"No woman puts up with, all this,"

"You know you keep gesturing to all of me every time you say that" Oliver interrupted

Tommy just smirked and continued,

"Just because. No woman fights so hard to fix a man's life for no reason. She is invested, she has given you everything she just isn't sure why yet. But I agree with Dig, it might be all on you to help her see it" he said placing a reassuring hand on his shoulder.

They all smiled at each other silently thanking their girl for her great heart and willingness to accept them all in her life. She truly was…..

"DING, DING, DING, DING, DING" Tommy's and Oliver's cell phones went crazy with messages and emails.

They both looked down confused and began to open the messages only to find that they were on the headlines of every gossip rag, blog and forum in Starling City. Oliver got a call from his mom asking him to come home this instant and explain himself and why she had received a call from the bank that he had spent over $250,000 on women's clothes and jewelry plus over another $100,000 in purchases all over the world, he assured her that there must be some mistake and that he would get it sorted out and be home as soon as he could. Tommy had a message from Laurel asking for answers and before he was even done reading it his phone rang, it was his bank. They were informing him that they had frozen all his cards because they had encountered charges of over $250,000 dollars around the world. Until it got sorted out his assets would remain frozen which would take 3 to 5 days.

They both looked at each other confused, Oliver immediately began to get the Hood look in his eyes and his voice grew deep, as he stated that he would get to the bottom of this. As they both got up to make more calls and get to the bottom of this, Diggle let out a hearty and uncontrollable laugh that stopped them dead in their tracks and made them turn to look at him beyond confused.

"Idiots, both of you. You do realize there is an outrageously angry hacker in the basement right now with all her computer equipment, right?" he said with a smirk.

It took them a second before they both caught up at the exact same moment and turned and looked at each other shouting "FELICITY!"

Diggle laughed again as his phone beeped, he looked down it was Carly it simply said "RESTAURANT, NOW!"

He looked up all the humor gone and said "Carly"

Oliver and Tommy both shouted "HA" and then all three ran to the foundry door knowing it would be useless because by now she would have changed the codes on the doors. As they banged on the doors and took turns calling her on her cell, she sat on her chair with her legs up on her desk and just smiled a triumphant smile, she would let them suffer a little bit longer before making it all disappear.

Her final move was to text all three of them, the final nail in the coffin.

Tip of the iceberg boys, mess with me again and see what happens. FELICITY 1 INCONSIDERATE ASSHOLE FRIENDS 0

They all knew they would be okay, eventually everything would fall into place and they would be great, and they had her to thank but, right now, right now they just needed to get this damn door open.


Let me know what you think and thanks for reading!

AN: Aninal style In-n-Out burgers come with the works including grilled onions, regular onions and thousand island sauce so the breath can be a little wicked right after hahaha.