Disclaimer: These wonderful characters belong to DC/CW/other acronyms.

A/N: This is primarily an Olicity story but be warned- there's a good helping of past Felicity/OFC in this chapter. Yes, a female character. Felicity Smoak is all kinds of perfect and I'd hate for the ladies to miss out...

Surprise 1: Old Flame

Since the Island, Oliver had turned into a very suspicious person. Being a bow-wielding, secret-keeping, ass-kicking CEO of a billion dollar corporation often did that to a person- and today was no different.

Starling City had been quiet by Operation Save this City standards lately. Roy had the Glades under a watchful eye and none of the one-percenters were making themselves a nuisance so Oliver found himself with wonderful and rare free time on his hands.

He had visited his mother, seen his sister, had lunch with Diggle and trained so hard that even his pecs looked like they had pecs. Down times were both horrible and wonderful and he found himself wondering about the very busy blonde IT hacker/Girl Wednesday/ rambling assistant in front of him.

If he didn't take downtime well, Felicity Smoak was even worse. He couldn't recall a day she hadn't dragged herself into either the office or the lair to help deliver justice and hack FBI networks. This morning, it was another day at the office and he could see her through the glass doors, staring at the screen and pounding the keyboard.

And yet, even on this sunny, unremarkable day when Isabel was choosing to freeze someone else with her icy demeanour, Oliver Queen was suspicious. It was 11:30 and Felicity hadn't even walked in to say hello to him yet.

No awkward questions about penetrating arrows, no thinly veiled attempts to get him to admit he enjoyed looking in mirrors and no stumbling over herself when she got a little bit too close to him. Sure, she'd grunted at him when he'd walked in and he'd taken her silence as news that nothing in his city was going astray- probably for the first time since he came back.

She wasn't exactly ignoring him or going radio silent but he hadn't realised how much he enjoyed the simple pleasure of conversing with Felicity. He glanced at the clock again- 11:31- and wondered whether Diggle would bust him out of the office for an emergency sparring match.

His eyes flicked to Felicity again and noticed a change in her demeanour. Now, instead of intensely glaring at the screen in front of her she was busy texting on her cell. Her face was screwed into a grimace and her lip was gently biting the corner of her wonderfully pink lips as she waited, probably for her mystery texting friend to reply.

Her phone beeped and Oliver's curiosity was officially piqued. She hesitated for a moment and then hurriedly started typing back. Normally Oliver, and Diggle for that matter, relied on Felicity to do the digging for them so he tried to ignore the irony of being desperately left in the dark.

Who in the world was Felicity Smoak letting perplex her in such a way and why the hell was Oliver letting a simple thing such as his friend's social life get in the way of enjoying a free day?

Her eyes drifted over and Oliver quickly turned, clearing his throat and leaning back into his chair. From his peripheral vision, he saw her stand and wait a second, as if to gain some courage.

That made him even more suspicious and remembered back to their early days together. The woman was fearless and had no problem giving him a piece of her mind. In fact, after his one coffee allowance, when he had teased her about another, she had destroyed the coffee machine and left it with a bow on his desk.

When it came to him- the Hood or the CEO- his girl Wednesday (Friday? he couldn't remember) was brave. So whatever was going on, he was going to get to the bottom of it. Luckily, Felicity was looking to make the first move.

He sat back slightly in his chair and smiled as Felicity threw open the door that separated them. Before he could even open to his mouth to greet her, she was in full Felicity babble mode.

"Mr Queen- Oliver. If it's okay with you, I'm going to lunch. Actually, I'm going, even if it's not okay with you. Which I'm sure it is. Because you're a great boss and-"

He decided to put her (and himself) out of misery. "It's fine, Felicity."

She visibly relaxed. He decided to push his luck. "Lunch with a friend?" She was quiet for a moment.

"Mmm hmmm," she confirmed, pursing her lips together. "From college," she added. "Long time ago, really. Old M.I.T friend. From college."

Oliver had been around the block a few times. He might've been a college dropout, but he was sure 'old college friend' easily translated into 'old flame'. She looked uncomfortable so Oliver tried to appear relaxed and not at all interested in the former college boyfriend Felicity was undoubtedly meeting.

Except, that he wasn't uninterested. "And your friend is here? In Starling City?" he asked, trying to appear natural. He was much better at keeping himself under control than Felicity was.

She nodded quickly. "Here for a work thing. So we thought we'd...catch up," she said vaguely.

Oliver thought for a second. "Does your friend have a name?" Diggle was at the foundry, he could probably run a name or two before lunch was over. He was sure the jig was up until Felicity sighed. "Chris. So, if it's all the same to you, I'm leaving now. For lunch."

"With Chris," Oliver supplied. "From M.I.T. Take your time and enjoy yourself. I think you've earned it."

Felicity smiled back at him awkwardly and with a quick wave and an assurance she'd keep her phone on for an emergency, she was gone. Oliver waited a full thirty seconds before he grabbed his phone and his jacket.

"Digg," he started as he pulled on his jacket. "I need you to track Felicity's phone and tell me where she's going."

"Is something wrong, Oliver?"

Something was wrong with him, clearly. But he wasn't about to admit to Diggle that because he was bored or protective or even curious, he was about to stalk Felicity's lunch with her old college boyfriend.

"Just forgot to tell her something. It's...important."

There was silence over the phone. "Important enough to...stalk Felicity," Digg finally said. "On her lunch break."

"Text me her location," he said and ended the call abruptly.

The small cafè wasn't far from Queen Consolidated. Felicity hadn't even bothered to take her car so Oliver had tried to stay a healthy distance away from the cafè so it didn't look as if he had followed her there. Which he totally had.

Something about the whole thing seemed odd. Whoever the guy was, Oliver didn't like it. Felicity had a tendency to ramble and for her to hold on to the information about this person she was meeting so tightly and not even spill a last name was enough of a clue that things hadn't exactly ended amicably.

A name or two had surfaced when he had run his own background check on her but he couldn't recall a Chris. For the most part, her life before Team Arrow hadn't been filled with danger or excitement but at least she was honest about it. Neither he nor Digg had pressed her too much, but occasionally a fact would slip out mid-rant.

Nothing about this 'Chris' though and that is why Oliver had waited twenty minutes after Digg had texted him to walk in. Without any pressing matters to distract him, Felicity and her mystery ex had filled his every thought since he had connected the dots.

He needed to know.

If anyone noticed that the great Oliver Queen was frequently the establishment, they kept it to themselves and he appreciated the lack of fanfare. The place was more on the cozy side than Oliver was used to but it didn't take him long to spot Felicity amongst the patrons.

A pillar was strategically blocking her coffee companion but he could see Felicity's face clearly. He was confused as ever. She looked amused and awkward all at the same time. Whomever she was speaking with was in mid-conversation. Felicity was engrossed in whatever Chris was saying which gave Oliver precious moments to order his coffee.

He wasn't sure what his plan was or if he even had one. All he knew was that he needed to get a look at Felicity's 'friend' and if he didn't, he was going to go insane. He looked down at the pair and realised there was a vacant table close by. After telling the staff to deliver his coffee, Oliver put his best foot forward and moved to his table.

He had only taken a total of three steps when Felicity caught his eye. At first she looked panicked, and quickly checked her phone. He felt like smacking himself-of course she would think there was an Arrow-related emergency. However, there was no turning back so he put his best foot forward.

Felicity looked more than startled as he headed for the spare table. He hadn't meant to disrupt her and a wave of guilt passed over him, but his curiosity was now insatiable. "Oliver?" And now, he was at his table so it was safe to turn around.

What he found was not what he was expecting.

Sitting opposite Felicity was a well-dressed, short-haired, brunette woman.

There were three possibilities here. One, Felicity lied to Oliver. Two, he had been way off base with his assumption. Or three, he was 100% correct and Felicity had once dated Chris.

Chris, the woman. Chris, the incredibly good-looking woman.

He cleared his throat. "Felicity."

She looked at him expectantly. "Is everything okay?" she asked hurriedly. He tried to avoid looking at her companion who was regarding him with a great deal of curiosity.

"Oh um, fine. I'm just here, waiting for my coffee actually."

He recalled other moments of lying to Felicity Smoak. She hadn't believed him then and there was no way in hell she was buying the crap he was selling. He finally turned to face Felicity's college friend.

"Oliver Queen," he said, extending his hand. "I'm Felicity's..."

"Boss," Chris filled in, accepting his hand. "Queen Consolidated. The Oliver Queen. Wow. I'm Christina."

Felicity did not look pleased. "If that's all Mr Queen, we were just..."

"Felicity!" her friend admonished. "The poor man is just waiting on a coffee. One without sugar, no doubt. Please, Mr Queen, you're welcome to wait with us."

The Plan was always to privately 'investigate' Felicity's lunch date but Oliver had no idea things would turn out so to be so uncomfortable. A million thoughts were racing through his head, none of them appropriate.

If he was being honest with himself, he had caught Felicity staring at him on a number of occasions. And she was always rambling, making inappropriate remarks, staring at him on the salmon ladder...had he missed something?

So now, instead of being wholly interested in her choice of company, Oliver was most interested in Felicity. He pulled up a chair. "Oliver, please."

He felt a swift kick to his shins but he ignored it. "I hope you don't mind me asking, but how is it you know Felicity?"

Christina grinned. "We're old college friends. Nerding it up at M.I.T, of course. After graduation, I got a job at Wayne Enterprises, Felicity ended up with QC and here we are."

"Here we are," Felicity repeated, staring into her coffee cup. "Chris was in town for work and I like eating with her so..."

For a split second, Oliver thought he caught the beginning of a smirk on Christina's face and a blush creep up on Felicity's neck, but in the interest of the mission, he let that one go.

So, innuendo seemed to follow Felicity around more than he originally thought. A moment later, the waitress appeared with food but no coffee for Oliver. Felicity made a point of reminding her that Oliver was still waiting on his coffee (to go, please) and returned back to gazing between him and Christina.

Felicity was a master of secrets, but he wasn't too sure which one she was insistent on maintaining. Thankfully, after one bite of her salad, her phone chirped at her.

She looked down at the call. He knew it wasn't Digg, otherwise his phone would be beeping right along with her. A personal call perhaps? She grimaced as she checked it.

"I'm sorry, I really need to take this," she apologised as she stood. "It's my brother. I'll be right back."

Christina waved her off she glared at Oliver. "Behave yourself for two minutes?" she snapped, just before answering her call. As she moved away from the seated area, he could help notice the smooth lines of her skirt and the way her lovely legs looked in her smart-casual flats.

"I know that look."

He turned to look at Christina. "Look?"

She smiled wistfully and nodded toward Felicity. "That look you just gave her. She's something else, isn't she?"

"She's remarkable," he answered honestly. "I mean, she's pretty pissed I moved her from IT..."

Christina nodded. "So I've heard. But I don't just mean her work. I mean that's amazing too, don't get me wrong, but that look isn't about you making eyes at her keyboard warrior skills."

He didn't respond.

"Look, I'm not trying to pry or anything," Christina started. "And I know you're a busy man being a billionaire CEO member of the Queen family, and hell knows I won't say a thing about inter-office relationships, but our girl's special. She doesn't do things by halves."

He couldn't help himself, and snuck another look at Felicity. "Christina, I hope you don't mind me asking..."

She chuckled. "She didn't say anything? I'm not surprised. Hey, I think she's great, but she's not perfect either." There was a pause. "Don't fall in love with a straight girl, right? College flings don't equate to epic love stories anyway."

The thought of Laurel danced through his mind quickly along with the various 'flings' he had enjoyed right under her nose through all four of his colleges. The thought of his past indiscretions nearly made him sick.

He raised his eyebrow. "Fling?"

She speared a piece of asparagus with her fork. "I have a girlfriend in Gotham now, anyway. What's past is past. I genuinely wanted to catch up with her. But like I said, I know that look."

He spied on her again. "At least she was honest with what she wanted. I looked at her more than once like that, Oliver. It's the look of wanting something you can never have. Of wanting to be consumed, wholly and wonderfully, even for a moment."

Before he could respond, the extremely apologetic waitress pressed his hot coffee into his hand. Felicity was still busy on the phone and Christina was looking at him with a knowing look in her eye.

He shouldn't have come here.

"I should go," he said quietly and stood, moving the borrowed chair back to its original position. "Could you tell Felicity..."

Christina smirked. "Your big secret? I'll pass. But I'll let her know you got your coffee." She extended her hand. "It was genuinely nice meeting you."

He shook it. "Goodbye, Christina."

"I can't believe you!" Felicity screeched as she dumped her bag on the desk next to the computers. He had arrived forty minutes ago and had already begun sparring with Diggle. His partner glared at the interruption.

"What'd he do this time?" Digg asked and Oliver got the feeling the poor man was afraid to ask. He had learned his lesson in the aftermath of the coffee incident. Oliver ignored Felicity and grabbed his bottle of water.

"Hello to you too," he mumbled as Felicity punched her code into the computers.

"Were you spying on me today? I can't believe you followed me! That is so...so juvenile!"

Digg raised his eyebrows and followed Oliver to retrieve his own drink. "He...stalked you?"

Oliver shot a glare toward Digg who turned to drink his water, avoiding the spat altogether. "Stalked! Stalker! You knew I was going to lunch to meet a friend..."

"Felicity, I'm sorry I ruined your lunch. I only wanted a coffee," he lied. "You see, my assistant ruined our machine and-"

A shoe went flying past his head. "Do not go there, Oliver."

"I'm just going to...go over there," Digg advised, grabbing his phone and moving away.

He took another drink of water and approached Felicity. He couldn't help notice how adorable she looked when she was pissed. He had seen her blush enough times to notice how it usually started at her neck and moved forward to expand over her beautiful cheeks.

He cleared his throat and lowered his voice. "You didn't need to lie to me, Felicity."

She stopped her movements. "It was none of your business."

Of course it wasn't any of his business. He felt a bit guilty for making it his business, especially after his chat with Christina at the coffee shop. He didn't say anything.

"It's just...ugh! Some parts of my life are private, Oliver! Christina might not be an island with things that hunt and maim you but I felt guilty about how things ended. I was a terrible friend after I told her emphatically that I was not a lesbian and I did, and still do, in fact, enjoy having sex with men...okay, not the point, but I wanted to deal with it myself. And you didn't let me do that!"

He was quiet for a moment.

"I'm sorry."

She straightened her back. "Thank you. I mean, if I'm seriously in danger, you have permission to stalk my whereabouts with Digg but no more spying. Can we please just..move on?"

Without consciously doing so, Oliver touched her shoulder. "Of course."

Before Felicity could reply, Digg had come out of his hiding spot. "Lyla says hi," he said weakly. "Back to it?"

Oliver nodded and pressed his water bottle into Felicity's hand. "See what the scanners are showing."

She nodded. "Um, could you pass me my shoe please?"

Digg smirked as he handed her her tan-coloured flat. She grabbed it thankfully and moved to her seat.

Oliver grabbed his training stick and threw Diggle his. "Felicity's a lesbian?" he asked quietly.

"I did, still do, enjoy having sex with men!"

Oliver only smirked. "Another round."

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