Roger knew for a while that Oliver had feelings for his best friend. He knew before Robert Queen's funeral. Even before the pot brownie incident, where Oliver literally spent the entire night camped out beside Felicity's bed to make sure she was alright. He hadn't known where Felicity was on the subject until Oliver told them that he wasn't coming back to MIT. Her disappointment went beyond the loss of a friend, and he planned to point that out on their way back, but then Oliver was at the doorway with his suitcase and the entire situation seemed moot. Roger could sense the shift between them during the ride to the airport. The loaded silence. The not-so-furtive glances. He watched the two of them sputter through Oliver's attempt to help Felicity hoist her bag onto the conveyor belt at the security check, and thought, game on.

And then, nothing happened.

At first, he thought it was just timing. They had the holidays, and while Felicity was staying on campus, Oliver headed back to Starling City after his exams. It made sense not to start anything when the school calendar dictated several weeks apart. But then, they all came back in January and for the entire month, through Friday-night-movies and countless dining hall meals, absolutely nothing changed.

"When are you going to ask Felicity out?" Roger asked point blank one night.

Oliver looked up from his computer screen and asked, "What are you talking about?"

"You clearly like her. She clearly likes you. I don't get it."

Oliver's jaw tightened, and he said, "I think it's better to not go down that route."

"Why?"

"It just is," Oliver repeated, the finality in his tone indicating that he thought the conversation had ended. It hadn't.

"Yeah, that still doesn't explain anything," Roger said.

Oliver let out a sharp exhale and closed his laptop. "Felicity is your best friend, right?"

"Yeah," Roger said leadingly. "Your point?"

"Then you should not want me dating her. I don't have the best track record when it comes to dating."

"I thought you dated the same girl all throughout high school? The one who made your life a living hell?"

"Yeah, I did," Oliver said, rubbing uncomfortably at the back of his neck. He had mentioned Laurel before, but he didn't share the full story. Namely, the part less flattering to him. "But, uh, I wasn't exactly blameless in that situation. I had a bit of an issue with exclusivity."

"Look, I don't know who you were back at Starling Prep, but here? I've seen about a dozen girls try to get your attention and you're always only looking at her."

Oliver shook his head, opening his laptop again, and said, "It's not happening. So, let's just drop it, okay?"

Roger shrugged, pretending to go back to his comic book. Oliver was being dumb and, as strong-willed as Felicity was, he knew his friend wouldn't make a move on Oliver by herself. So, it seemed like he was going to have to play matchmaker.

Felicity had never been a big fan of Valentine's Day. She worked part-time during high school, which didn't leave much time for dating. And for the brief period of time she actually was dating someone, he didn't believe in Valentine's Day, telling her it was a made-up corporate holiday.

Several groups on campus sponsored candy-grams, where you could send people little valentines that were delivered throughout the week leading up to Valentine's Day. Despite her general apathy to the holiday, Felicity still found herself perking up every time one of the students came in to a classroom or a dining hall, bag filled with valentines. One particular afternoon, Roger noticed her do just that, and said, "I thought you didn't care about Valentine's Day."

"I don't," she said, her eyes tracking the student as he walked around, delivering the valentines.

"Because it sort of seems like you care right now," Roger said.

The guy pulled out a small bag of candy and read aloud, "Is there a Felicity…" he looked at the valentine closer, "Smoak? Felicity Smoak?"

"That's me!" she said, voice unnaturally high. She raised her hand and repeated, "That's me."

The guy waked over and handed her the valentine. It was attached to a tiny bag filled with candy hearts. Felicity looked at the card, wondering who it was from, but it wasn't signed.

"Maybe it's a mistake," Felicity said. Her chest tightened when she lightly ran her fingertips along the edge of the valentine. Maybe it was a mistake. Or maybe it wasn't. Maybe there was someone out there thinking of her.

Roger shrugged, and they dropped it, but then later that day, during her computer science class, she got another valentine, this time with a single rose. The next morning, during breakfast, there was another.

"Looks like you have a secret admirer," Roger said, taking a large bite of his bagel.

"I wonder why he won't sign his name," Felicity said.

"Or she," Roger said. "It's 2020, Felicity."

She smiled and smacked his arm. "It's sort of exciting, isn't it?" She glanced over at Oliver, who was suddenly finding his oatmeal very interesting. "Or at least I think it is."

Oliver felt her gaze and he looked up, clearing his throat and saying, "Yeah, it's exciting. Sure."

"Oliver's just salty because no one has sent him any valentines," Roger said. "You know, I could send you a pity one."

"I don't need a pity valentine," Oliver said sharply. His voice softened when he looked over at Felicity and said, "It is exciting, Felicity. I'm happy for you."

There was a note of something strange in his voice, but before she could fully process it, a group of people began loudly singing on the other side of the cafeteria. Roger looked over his shoulder and said, "Ah yes, the singing-gram."

"They're really good," Felicity noted.

"Wishing that your secret admirer would send you one of those next?" Roger joked.

"Only if we're not with you," Oliver said, standing up. "I'm going to head to class."

"But it's not for another hour," Felicity said with confusion.

"Yeah, I know. I have some reading to finish for it. I'll see you guys later."

Felicity watched him walk away and said, "Is it just me or is he acting weird?"

"Maybe he's jealous."

Felicity snorted. "Yeah right."

"It's not a ridiculous thought," Roger said. "I told you-"

"I know, you think Oliver has a thing for me," Felicity said. "But, hey, guess what? If Oliver had a thing for me, he would do something."

"You don't know that."

"When someone likes a person, they do something," Felicity continued, stabbing at a piece of fruit with her fork. "A simple, hey, want to get some dinner? Or coffee. They ask you for coffee."

"Oliver doesn't like coffee."

Felicity rolled her eyes. "You know what I mean. But, it doesn't matter. I don't need Oliver to take me out for coffee or dinner." She picked up the valentine, smiling slightly. "Because now I have a secret admirer."

Two days later, Felicity received her fifth valentine from her secret admirer. Except, this time, her secret admirer asked for them to meet. The plan was simple. If Felicity accepted the proposal, they would meet on Valentine's Day at 12:00 at the center of the quad. Felicity sat with Oliver and Roger during their movie night, debating whether she should meet him. Valentine's Day was tomorrow, which meant the clock was ticking for her to decide what to do.

"I think you should go," Roger said. "I mean, what's the worst that could happen?"

"He could be a serial killer," Oliver supplied.

"Gee thanks, Oliver," Felicity said. "I really appreciate the vote of confidence."

"Can we just get back to movie night?" he said. It felt like all their time this week was spent talking about this mystery guy, and frankly, he was sick of it. "I really want to see what happens to Captain America."

"You know what happens to Captain America," Roger said. "We watched this last week."

Oliver looked at his roommate, jaw tight, and said, "Well, I want to see it happen again."

"I feel like I'll regret not going," Felicity said, ignoring him. "I'd regret it, right? Yeah, I'd definitely regret it. But maybe…"

"What are your thoughts, Oliver?" Roger asked.

"I don't have thoughts," Oliver said. "And I really would like to stop talking about this."

Felicity felt a flare of anger and said, "Well, sorry buddy, but this is what we're talking about right now. If you don't like it, you can leave."

"We're at my dorm."

"Too bad!" she shot back.

"You want to talk about it?" he returned loudly. "Fine, we'll talk about it. I think all of this is ridiculous. I think you're wasting hours obsessing over someone who's too much of a coward to even let you know his name."

"It's romantic," Felicity held.

"No, it's pathetic," Oliver said, voice hard.

Felicity stood up quickly, her hands balled into fists at her sides. "You're a jerk, Oliver. Do you know that?"

"Hey guys, let's just calm down," Roger said, looking between them warily.

"You're supposed to be my friend," Felicity continued angrily. "And you can't even let me have this one thing."

Oliver felt guilt wash over him, and he quickly said, "Felicity."

But she was already gone, slamming the door behind her.

"Well, that went well," Oliver said, slumping against his bed. He looked over at Roger, who he noticed looked a bit pale, and said, "Don't worry, I'll apologize to her tomorrow."

"So, um, I have to tell you something," Roger said.

Oliver looked over at his roommate. "What is it?"

"No one is meeting Felicity at the quad tomorrow."

"What?"

"I sent the valentines," Roger said.

"You did what?" Oliver hissed.

"You both were so stubborn about your feelings! And I thought that if you were faced with the chance of her being with someone else, it would force you to do something. But instead, you two just ended up doing that."

"She'll be crushed if no one shows tomorrow."

"I know. But, you could go."

"Roger, stop," Oliver said. "Just stop this shit, okay? I told you, that's not going to happen. Respect it."

"It's dumb," Roger pressed irritably. "All of it is dumb! I see the way you look at her. I saw the way you reacted when there was the possibility of her being with someone else."

"I'm not having this conversation," Oliver said, getting up from his bed. He grabbed his keys from his nightstand and headed toward the door. Roger asked where he was going, and he said, "Out."

The elevators had been running slow all week, so Oliver went straight to the stairwell, stopping short when he found Felicity. She was sitting on one of the steps, shoulders hunched. She looked back, wiping at her eyes and groaned when she saw that it was him.

"Of course, it's you," she said unhappily.

He hesitated before sitting down next to her. "I'm sorry for being a jerk."

"Why can't you just be excited for me?" Felicity asked. "Roger is."

Oliver took a sharp inhale and said, "Yeah, well, Roger and I aren't exactly on the same page about a lot of things right now."

"I know it's silly. I mean, a stranger is sending me valentines. I know what it looks like. But, what if it's something good? What if it's a start?"

"I don't think you should go tomorrow."

Felicity scoffed, beginning to stand, and he gently took a hold of her arm to stop her. "I'm not trying to be mean here, Felicity. I just don't want to see you get hurt."

"You don't think he'll show."

"He might not," Oliver said slowly. "Or he could not be what you expect. I care about you, Felicity, and I don't want to see anything happen to you."

She turned her head toward him and asked, "Why do you care so much?"

He blinked rapidly and said, "I'm your friend."

"Right," she said, looking away. She stood up and said, "I appreciate your concern, but I made my decision for tomorrow. I'm going."

Roger tried to fix his mistake the next morning. He called Felicity and told her that he sent the valentines, but she wasn't having any of it.

"Oliver put you up to this, didn't he?"

"No, Oliver has nothing to do with it," Roger said. "I sent you those valentines."

"And why in the world would you do that? To admit some secret love for me? Come on, Roger. Oliver clearly got into your head. I'm going today. End of story."

"This isn't good," Roger said, pacing in his and Oliver's room. "This really isn't good. She's going to go there and be stood up. We have to go."

"No, I'llgo," Oliver said. Roger went to argue, and Oliver said, "I'm pretty sure if you go and she finds out what you did, there will be some bodily harm. Probably better for her to cool down before she sees you."

Roger nodded, sitting down on the edge of his bed. "I really messed up here, didn't I?"

"It's definitely not your finest moment."

"I just thought…" he trailed off, shaking his head. "It doesn't matter now. Will you just tell her I'm really, really sorry?"

Oliver nodded. "I will."

Felicity stood in the center of the quad, her stomach flipping every time a man walked toward her, but then he would continue walking, right past her and on to wherever he was actually going. She checked her watch.

11:58.

There was still time. Oliver didn't believe it, and he somehow convinced Roger to turn on her, too, but she believed. There was someone out there for her and he was meeting her in the quad at 12:00.

"Felicity."

She closed her eyes, exhaling sharply. She should have known he would come and try to interject himself into this.

"Oliver, please just go."

"No, I can't."

"Why not?" she asked, turning around to face him. "Your legs look like they're working just fine. Go."

"I can't," he said.

"Why? Why can't you leave?"

"Because I'm the one meeting you."

She stared at him with confusion. She had already been nervous before, but now it felt like her heart could beat clear out of her chest. "What are you talking about?"

"Roger sent you those valentines. And it was because of me. He was convinced that I had feelings for you and he thought if I was faced with the chance of losing you to someone else, I would come to terms with them."

"That's ridiculous," she said. He didn't respond and she said, "That is ridiculous, right?"

Denying his feelings to Roger was one thing, but denying them to her was more difficult. She was gazing up at him and he could see her chest rise and fall rapidly as her breath quickened. It would be so easy to tell her the truth. To give in to what he had been feeling for longer than he cared to admit.

"Felicity?"

They turned around, Felicity surprised to see this guy, Matt, from her civics class, standing behind to them.

"Hi Matt," she said, glancing at Oliver. "Can I help you?"

"Um, I'm the person you were supposed to be meeting here. Middle of the quad at noon?" Felicity stared at him. "Surprise?"

"Wait, so you're telling me there was another person who wasalsosending her valentines?" Roger said. "And he also asked to meet her at noon in the middle of the quad?"

"I know. I can't believe it either," Oliver said.

"Are you sure that's what actually happened?" Roger asked with disbelief. "Because that's crazy."

"I checked it out before I left," he said. "Turns out she had an actual secret admirer after all."

"But, how did she not think it was weird to get two invitations to meet?"

"She said she only got one. The other one must not have been delivered."

"Huh," Roger said, staring off into the distance. "I have to say, of all the ways I thought this could go, this was not one of them."

Oliver shook his head. "Yeah, I know."

"So, right now she's…"

"With him." Oliver stood up. "I'm going to go for a walk."

An hour or two later, Oliver came back. He took a quick shower and had just changed into a pair of sweats and a t-shirt when there was a knock on the door. He opened the door to find Felicity standing there. She looked nervous, and asked, "Can I come in?"

"Yeah sure," she said, stepping back.

Roger sat up from his bed and immediately began to say, "Felicity-"

"Catfishing me?" she interrupted. "Seriously?"

"I'm sorry, it was dumb. Super dumb."

"You think?" she said.

"I'm really, reallysorry and I promise to never do anything like that again. I've learned my lesson that subterfuge is really not my strong suit."

"It's really not," Felicity said. "Do you think I can have a moment alone with Oliver?"

Roger nodded, skirting around them with an apologetic glance before leaving them alone in the room. Oliver expected Felicity to speak first, and when she didn't, he asked, "How was your date?"

"It was fine. He's nice."

"That's good."

There was a pause and they both went to talk at the same time. Oliver smiled slightly and said, "You go first."

"I wanted to ask you something about before," she began slowly. "You said that Roger sent me those valentines because he thought you had feelings for me and I said that was ridiculous."

It wasn't a question, but he nodded anyway.

"Is that ridiculous?" she asked. "Because, sometimes…sometimes, it doesn't feel that ridiculous. But, then I look at you and then I look at me, and I think, hello, totally ridiculous."

"It's not," he said immediately, unable to ignore the insecurity in her words.

"Okay," she said, her voice catching. "So, it's not ridiculous. What does that mean?"

He let out a shaky breath and said, "It means that I think you are one of the most remarkable people I have ever met."

She stepped toward him gingerly, waiting to see if he would put distance between them, but he didn't. She braced her hands on his chest, gaging his reaction before she reached up and touched his face. She met his eyes, noticing the conflict there.

"I could hurt you," he said.

He expected her to refute that, but instead she said, "Yeah, you could. And I could hurt, you, too. But those are risks I'm willing to take." She took a deep breath. "If you are, too."

For all the concerns he had about starting something with her, they were not stronger than the feeling of her fingers against his cheekbone. The warmth of her palm through his shirt. And so, he reached up and covered her hand with his own. Lowering his head to hers, he kissed her softly until her hand slid to the back of his head, fingers threading through his hair as she deepened the kiss. When breathing became necessary he pulled away, forehead pressed against hers.

"Hey, Felicity," he murmured.

"Yeah."

He brushed his lips once more across hers. "Happy Valentine's Day."