Chapter Text
“The Five Times Oliver Failed to Convince Felicity That He Loves Her and The one Time That Diggle Did It For Him”
Word count: 3,071
I.
The day Oliver decided that he was tired of pretending that he didn't love Felicity like more than a friend, had been a pretty normal one. Well, normal as in their sense of normal, that is.
It had been all about early morning meetings, trying to get Queen Consolidated back and late night Arrow business. Oliver ha known all along that he loved Felicity, because his admission during the final battle against Slade, had n't been planned at all. The three little words had slipped out of his mouth and he had stopped for a moment himself, thinking about the truth they held while waiting for Felicity's reaction.
L ater, he had tried to convince himself that love didn't have to be romantic love. His love for Felicity could be very platonic...or as platonic as they tried to convince themselves that it was.
Nevertheless, when he had walked back into the new lair that night, and he'd seen her stand from her computers, waiting for him despite him telling her that it was a slow night and that she could go home earlier.
“I couldn't leave knowing you were still out there,” she had told him, wringing her hands nervously. “I mean, I knew that you would be fine, but I sort of like seeing you so I know for sure.”
He stood by the stairs, frozen for a moment before walking up to her calmly. She looked at him curiously and he opened his arms for her. She stepped into them without hesitation, hugging him back just as tightly as he was holding onto her.
And that was when it all came crashing down for him.
His heart beat loudly in his chest and his fingers felt all warm and tingly, and not just because they were still covered with his leather gloves. He rested his chin on the top of her head and inhaled through his nose, her familiar scent filling his nostrils.
He had been stupidly trying to pretend that he wasn't in love with the woman he was embracing and in that moment, he decided that he needed to tell her that he loved her, as more than a friend.
“I love you,” he mumbled into her hair.
Briefly, he felt her tense in his arms. This was the first time he had said the words after that night in the mansion.
I t felt as if hours had ticked by when she finally relaxed again against him. “I love you too, Oliver,” she told him and he pulled away a little so he would be able to look into her eyes. “Just like I love Diggle. The two of you are my best friends in the entire world.”
Wait... What?
Oliver backtracked in his mind, processing her words for a moment.
Oh. Oh!
She thought he meant that he loved her as a friend!
“Well, since you're okay and I saw you myself, I need to go home and get some rest,” she told him casually, stepping out of his embrace while walking back to her computers to shut them off. “I've got a job interview at Kord Industries tomorrow morning and I'd hate for my potential new boss to mistake me for a zombie,” she laughed.
Oliver was still frozen in place, looking a little dumbfounded, to be honest. When Felicity finally told him good night and headed out, he mumbled his reply to her before slowly changing out of his Arrow suit. It would clearly take a lot more effort to convince Felicity that the love he was talking about was far more than platonic.
II.
The second time he tried to tell her was a complete failure.
Actually, he figured it would be really romantic, but of course, fate wouldn't have that.
The two of them were sitting close to each other on her couch, watching a movie together after yet another long day. An almost completely empty tub of ice-cream was on her table, two spoons sticking out of it and Felicity had draped a blanket over them before cuddling into Oliver's side. He had taken a hold of her frozen hands, warming them with his own and his warmth breath, looking up at her every once in a while from under his lashes.
Felicity had obliviously kept looking at the TV, thanking him later for warming her up before then going on a full on babble about 'sharing body heat' and how 'two friends as close as them could do so in the most platonic ways ever, without it being weird'.
After that, they had fallen into a comfortable silence, Oliver's arm wrapped around her shoulder, bringing her closer to him as she rested her head on his shoulder. He liked that, very much.
“Felicity,” he whispered after a while.
“Hm?” she hummed in reply.
“I want to say something,” he declared. He waited for her go-ahead, but never got it. “Felicity?” he turned to look down at her, only to find her fast asleep on his shoulder, a small smile playing on her lips.
Of course she was a sleep; just his luck.
“I love you,” he murmured anyway before pressing a light kiss to her forehead. The action made her snuggle in closer to him and he couldn't help but smile. He could tell her that he loved her another day. She was tired and would most likely be very grumpy with him if he woke her up.
His own head fell to rest on top of hers, before sleep finally overtook him as well.
III.
Third time is a charm, Oliver figured, but was once again proven wrong.
To be completely honest, the third time he told her that he loved her hadn't been in a calm situation at all.
She had been late to get to the lair and he had already been antsy because he worried that something might have happened to her. So when Roy and Diggle asked her how her “date with Mr. Kord” went, Oliver completely lost it.
“You were late because you were on a date?” he asked her incredulously.
“I'm sorry, Oliver,” Felicity replied. “I was having such a great time and I figured that five more minutes wouldn't hurt. Then of course, I got stuck in traffic and-”
“You were on a date with your boss?” Oliver interrupted, shooting a glare her way. “And that date made you forget that we have a mission to protect this city and the people in it?”
Felicity frowned at him, taking a step back, setting a safe distance between them. “What are you even saying, Oliver?” she asked him. “Because it sounds to me like you're trying to tell me that I'm neglecting my duties and leaving the team behind completely. I was twenty minutes late, not boarding a plane to Italy to leave you guys behind!”
“You were late because you were on a date!” Oliver hissed back, not even noticing Diggle and Roy shifting uncomfortably behind Felicity.
“Why do you say it like that?” she demanded. “Like there's something wrong with the fact that I actually managed to get asked out by a nice guy?”
“You were late, Felicity,” Oliver repeated, as if that would explain everything.
“And I said I was sorry,” Felicity pointed out angrily. “How is this any different from the time I tried to get a hold of you while you were hooking up with McKenna while your other psycho ex-girlfriend came to my office and tied me up? At least you weren't threatened with a crossbow!”
“It's different,” Oliver countered lamely.
“How? How is it any different? You were on a 'date' and got my call too late, and I was on a date and got here a little later than I said I would, but I got here, which is the point. So tell me, Oliver, how is it different?” she ranted.
“It's different because I love you!” he blurted out, taking a big step forward, towering over her. He was still angry, but not at her. Instead, he was angry with himself for being jealous over the fact that she had gone out with someone other than him, even though he didn't have a claim on her.
“So? I care about you too, but you don't see me going off on you every time you're late because you had a late night,” she shrugged, standing her ground.
“No, Felicity, I love you,” Oliver repeated, but she only kept glaring at him.
“I heard you, and I love you too,” she said as-a-matter-of-factly, just as Oliver realized that there would be no getting through to her tonight either. “But that doesn't mean you get to be a protective asshat just because you were a little worried about me. I worry about you, Diggle and Roy all the time, but I don't go crazy on you when you return to the lair.”
So she had picked up on the fact that he had been worried about her.
He glanced at Diggle and Roy who were standing behind her still. By the look in their eyes, he knew that they at least had understood that he'd been sincere when he told Felicity that he loved her. Now it was out there, but Felicity, was as oblivious as she'd been before.
“Okay,” Oliver finally sighed. “I'm sorry. Can we just get back to work now?” he asked her.
She nodded curtly before walking off to her computers. Oliver looked up at Diggle who was looking at him as if he really wanted to make a comment, while Roy tried hard not to snicker at him. “Not. A. Word,” Oliver ground out before grabbing his suit to go and change.
IV.
When Oliver realized that Felicity would never believe him if he just kept telling her that he loved her, he decided to change his strategy. He would show her that he loved her, because what was that old saying about actions speaking louder than words?
So he did. Try to show it, that is.
He opened the door for her when they arrived at the lair at the same time, walked her to her car every night when she'd wait for him to return. Every evening, he asked her about her day and if she ever complained about a long day at the office, he suggested they grab some dinner together.
He bought her flowers every once in a while too, mostly the day after one of those particularly difficult days and he let her talk for hours and hours about whatever she wanted to, just so that she wouldn't have to carry any weight in her chest.
It all backfired one day when he brought her a bouquet of pink roses when she'd invited him home for a movie.
“Oh, Oliver!” she'd exclaimed happily, taking the roses from his hands before embracing him tightly. “Thank you so, so much! I honestly can't believe how lucky I am to have a friend like you.”
She kissed his cheek before hurrying off to find a vase to put the flowers in, while Oliver was left standing by her door. He was beginning to hate the word 'friend', he realized. Especially when it came out of Felicity's mouth.
V.
“You don't understand, Dig,” Oliver complained. “I've been trying to get through to her for months now. Either she stubbornly believes that I really don't love her, or she's just too distracted to realize what I'm actually trying to tell her.”
Felicity was out on another date with Ted Kord and Oliver had finally broken down about the entire ordeal in front of Diggle.
“Have you tried to just sit down and tell her?” Diggle asked. “Because truth be told, you're being pretty obvious when you walk around with heart eyes. I can't believe she hasn't noticed it yet...”
“I've told her so many times, but she keeps thinking I love her as a friend,” Oliver bitterly said. “I tried telling her again last night at that charity event we were invited to.”
“Yeah, would you like to explain that? I never really understood why she got so mad at you,” Diggle said as he cleaned his gun.
“Some old business partners came up to me while Felicity and I were dancing and I wanted to introduce Felicity, but I sort of froze because I didn't even know how to introduce her,” Oliver explained. “I mean, she's not my E.A anymore since I'm not CEO of Queen Consolidated, and she's my partner, but at the same time, I feel like she's a hell of a lot more than just my partner. So Felicity got annoyed because I accidentally slipped up and called her 'my Felicity', which made the business men laugh.”
“Oh,” Diggle chuckled. “Well, that must have been embarrassing for her. I understand why she got so mad at you.”
“And when she asked me what that was all about, I tried to explain myself and told her how she was way more than just my partner to me, because I love her, and once again she mistook my love for her as something platonic,” Oliver groaned. “I just can't seem to get through to her, and meanwhile, Ted Kord,” he spat, “is taking her out to dinner every week.”
“Oliver, green might be your color, but jealousy really doesn't suit you,” Diggle smirked.
“God, Dig. You don't know how frustrating it is for me... I thought she felt the same way about me and that she would be happy to know that I'm ready for us, but I just can't-”
“Get through to her?” Diggle finished for him. Oliver hung his head and nodded. “God, Oliver,” Diggle sighed. “Do you want me to give it a try?” the older man asked.
“Could you?” Oliver asked, running his hand over his face. “I really don't know what else to say to convince her.”
“Well, you could always just kiss her senseless,” Roy suggested as he walked over to them. Oliver had been so caught up in his conversation with Diggle that he hadn't even heard him walk into the lair.
“You don't think I've already thought about that?” Oliver asked. “I just don't think that is the way to approach her. What if she doesn't feel the same about me?”
“Oh, believe me,” Roy scoffed. “She does. The two of you are just equal amounts of stubborn that you don't allow yourselves to believe the truth, even though it's been in front of you the entire time.”
Oliver watched as Roy sat down and began sharpening some arrows, before turning to Diggle. “So you'll talk to her, right?”
Diggle sighed exasperatedly, “I'll talk to her, Oliver.”
VI.
“It's been so long since we've had burgers together, Dig,” Felicity said, sitting down in one of the booths at Big Belly Burger. “Just the two of us, that is,” she clarified quickly. “Not that I mind Roy and Oliver, but you know, sometimes I just miss having one-on-one conversations with you.”
Diggle smiled at her as he sat down across from her. “Yeah, speaking of one-on-one conversations,” he began slowly. “I have something that I'd like to talk to you about.”
“Oh yeah?” Felicity asked, taking a sip from her smoothie. “Sounds serious. Everything okay?”
“Everything's fine,” Diggle shrugged. “I just wanted to ask you when you were going to realize that Oliver is in love with you.”
Felicity choked on her drink and quickly grabbed for a napkin, covering her mouth with it as she coughed wildly. Diggle remained impassive, waiting for her to get herself together.
“What?” she laughed nervously. “Oliver isn't in love with me. What gave you that idea?”
Diggle shrugged. “I don't know whether it was the fact that he's been telling you for months now, or the fact that he looks like a lovesick puppy that's been kicked around every time you bring up Ted Kord or dating in general.”
“Dig, you're being ridiculous,” Felicity said. “Ted and I have decided that we're better of as friends because of the whole 'he's my boss'-thing. And Oliver hasn't said anything about being in love with me.”
“Oh,” Diggle drawled. “So when he snapped at you in the lair after your first date with Kord, when he told you he loved you, that wasn't him telling you that he really loves you?” he asked.
“He meant it like a friendly love,” Felicity insisted, pushing her glasses back up her nose, from where they had ridden down.
“And I guess buying you flowers is something he's always done?” Diggle continued.
Felicity frowned at him. “Maybe he just learned that I really like flowers?” she suggested. “Friends by friends flowers, Dig. It's no big deal.”
“Yeah, and Oliver has always been such a gentleman when he pulls out your chair for you, or holds your coat for you when you're getting ready to go home,” Diggle rolled his eyes. “Or when he opens doors for you and orders your favorite food every time you're feeling down... And lets not forget the fact that he has been telling you that he loves you. I mean, that's just something Oliver does, isn't it?” he sarcastically remarked.
Felicity seemed to think about what Diggle was telling her and Diggle could almost see the wheels turning in her head. Inwardly, he groaned, wondering how such a bright woman could be so daft when it came to realizing that the man she loved had finally realized that he loved her back.
All of the sudden, Felicity's eyes widened and Diggle sighed in relief when he realized he had gotten through to her.
“Oh my God,” Felicity said. “Oh. My God. He loves me!” she blurted out, staring at Diggle with eyes wide as saucers. “Oliver is in love with me!”
“Yes,” Diggle confirmed.
“Oh my God!”
“You said that already, Felicity,” Diggle chuckled. “Twice.”
“He's in love with me,” she repeated, clearly surprised by the revelation. She stood abruptly from the table. “Dig, I'll pay you back some day, but right now, I really need to go find Oliver,” she explained herself.
“It's okay, I've got it covered,” Diggle replied, holding his hand up. “Just remind Oliver that he owes me favor.”
Felicity nodded and hurried out of the restaurant as Diggle leaned back in his seat, satisfied with his accomplishment to get through to the blonde.