A/N: Huge thanks to justanother90sbaby on Tumblr for being my beta for this chapter! I was totally overthinking some things and she brought in some much needed perspective. Hope you like it. (I may have stayed up all night writing this hehe)

After Oliver's last conversation with Felicity, he spent an entire week tossing and turning at night. Her words kept haunting him, and he knew he had a decision to make. He was at a crossroads in his life, but he didn't like any of the options before him.

He called in emergency help, urging his best friend to hop on a jet to meet him in Cambridge. They met at Oliver's favorite table in his go-to coffee shop, both sipping on his beverage of choice.

Tommy nodded his head in appreciation. "You're right, this is good."

Oliver smiled. "Told you, man. Best latte in town."

"How'd you find this place?"

"A friend," he replied, smiling enigmatically.

"Uh huh." Tommy raised an eyebrow, giving him a knowing smirk. "A lady friend, perhaps?"

Oliver shrugged. "Maybe."

"Let me guess," he said, throwing up his hands. "She brought you here the morning after."

Oliver shook his head with a smile. "No, actually. We've never hooked up."

"What?" The omission earned an indignant cry from Tommy, "You losing your touch, man?"

He shook his head again. "It's not like that, not with her."

"Woah," Tommy replied, taken aback. "Who are you, and what have you done with Ollie?"

Oliver shrugged. "She's just different."

Tommy threw up a hand again. "Dude. You are not allowed to fall in love or become some whipped, lover boy. We're still young! We're in our prime! I need my wing man!"

"It's not like that either," he reassured. "Jesus, calm down."

Tommy pulled up his sleeves and leaned forward. "Okay, good. Now, is this girl the reason you asked me to fly three thousand miles to see you?"

"No," Oliver replied, before correcting himself. "Well, not exactly."

Tommy raised his eyebrows. "Explain."

Oliver leaned back in his chair and sighed. "I'm thinking about dropping out." He looked at Tommy, waiting for his reaction.

He didn't say anything, waiting for him to continue. "Is that it? Or is there more?"

He rubbed his forehead, the arguments in his mind circling around and around again. He decided to let it all out, figuring Tommy could help him process his thoughts.

"It came up in conversation that I'm not thrilled being at Harvard, and she suggested that I should try and find happiness my own way. So I'm thinking of dropping out. But if I do that, my dad will be pissed, and I'm worried that he'll cut me off. Which he all but threatened to do.

"But I hate being here—with one exception. This girl I met. She's the only reason I would stay, but I know that's not a good enough reason. Besides, she's crazy smart, and I feel like I wouldn't have much to offer her if I dropped out. And if I did drop out, and my dad did cut me off, I'd basically be a homeless nothing, and then I wouldn't feel right pursuing a girl like Felicity. But the thought of staying in school just kills me inside, and I really, really, don't want to work for my dad, but the thought of dropping out and moving back home, so far away from Felicity makes me just as sad, and fuck..." He dropped his head in his hands. "I don't know what to do."

The silence between them stretched out, far longer than Oliver was comfortable with. He lifted his head to look at his best friend, finding a contemplative look on his face.

"Well?" Oliver prompted.

Tommy took a deep breath and sighed, folding his hands in front of him. "Ollie. You know I love you, right?"

He nodded.

"And, nobody knows you like I do, would you agree?"

He nodded again.

"Dude. This is not the first time you've had this crisis. You remember Rebecca at Brown?"

Oliver sank in his seat. He nodded again, sulking a little this time.

"Or Jenny at UCLA? Laurel after graduation?"

His head returned to his hands. "Okay, okay, what's your point?"

"My point, Ollie, is that you fall in love really easily. I mean, I get it. Your parents didn't pay enough attention to you, so when a beautiful woman gives you that kind of attention, you soak it up like a sponge, and you think you're in love, but buddy…" He slapped him on the shoulder. "You're just infatuated."

A part of Oliver wailed against his friend's logic, not ready to let go of the idea of Felicity Smoak. "But what if this one's different?"

Tommy pinched the bridge of his nose. "So what if she is? Are you anywhere near ready for her?"

Oliver didn't have anything to say to that.

"Look," Tommy said, softening his voice. He leaned closer to Oliver, looking directly into his eyes. "You need to figure out what you want for yourself before you go looking for love, because let me tell you, man…a woman is not going to fix everything."

He looked at Tommy skeptically. "Where the hell do you come up with this stuff?"

His friend threw up his hands indignantly. "What? I watch Dr. Phil!"

Oliver laughed. "Jesus, Tommy, you cannot be spouting Dr. Phil at me right now."

"Say whatever you want, that guy knows a thing or two. Besides, I know what I want. I want to have a good time while I'm young, and when I meet the right girl, that's when I'll settle down. Until I meet her, I have no interest in doing shit."

Oliver shook his head. "The wise words of Tommy Merlyn, everyone."

"Fuck you, man. You know I'm right."

Oliver rubbed his head. "And what about my dad, and school?"

"Fuck, I don't know. Maybe you should talk to your mom first, play on her emotions. Get her to talk to your dad."

Oliver chuckled. "Jesus," he muttered. "You're a manipulative son of a bitch."

"Hey," he defended, "I'm my dad's son. I can't help it."

Oliver's fingers continued to worry the skin over his eyebrow. "So I should just walk away from this girl?"

Tommy sighed again. "What the hell would you do if you stayed? Who says she's even looking for a relationship? Or that she's interested in you that way?"

"I think she's interested."

"Ollie, you're not listening to me. You're still hanging on to your infatuation. You're like a kid with a fixation, and you want to have it now. I get that, too, because we're both spoiled rich kids used to getting our way, but women are not things. I know it's hard for you to realize this, but she's not your one and only."

A part of Oliver couldn't accept that. "But what if she is?"

Tommy rubbed his face with his hands. "If you were meant to be with her, if she really was your one and only, then fate will find a way to bring you two together, when you're both ready. But you. Are. Not. Ready." He punctuated each word with a finger to Oliver's shoulder.

Oliver thought for a moment, shaking his head in wonder. "How is it that you're the wiser one of us?"

"I'm not wiser, Ollie," Tommy smirked. "I'm just more practical. You're the romantic."

Oliver huffed a laugh. "Oh yeah. That's why we work so well together."

"Exactly," his friend agreed emphatically. "We're two sides of the same coin. Frick and Frack. Mike and Ike."

Oliver sighed. He knew what his decision was. He could always trust Tommy to lay it out in black and white for him. "Wanna come help me pack?"

Tommy looked up from his latte in surprise. "Really? Just like that?"

Oliver shrugged. "I'll just hitch a ride with you. No sense postponing the inevitable."

A slow smile crept over Tommy's face. "All right! Starling's most eligible bachelors are back in business!" They slapped their hands together and then pulled them apart. "You have so much catching up to do!"

Three hours later, Oliver was done packing. As his possessions were taken out to the limo, he shared a few final shots with his frat brothers. He had announced cavalierly that he didn't feel like being in school anymore and was going to spend some time living free of responsibility, to which they all toasted to him boisterously. He was going to leave his mark at Harvard like he had left his mark on the other universities; the legendary Oliver Queen, playboy billionaire.

It was all a mask, and a familiar one at that.

He only had one more stop before leaving Cambridge forever. To see someone who saw behind the mask.

The limo stopped in front of her dorm. The door was opened for him, and he looked at Tommy. "Do you want to meet her?" he asked tentatively.

"Do you want me to?"

He thought about it for a second, and then nodded his head. "Maybe you'll see things differently and tell me I'm crazy."

Tommy shrugged. "All right."

Butterflies attacked his stomach the entire way up to her room. He took deep breaths, trying to control his anxiety. He knew this was the right thing to do, but he couldn't help feeling a bit panicked at the thought of letting her go.

"Jesus, look at you," Tommy remarked, smirking at him. "You really do like her, don't you?"

He ignored him completely, keeping his mind on the words he was practicing in his head. They reached her door, and he hesitated a couple of times before knocking. With a final deep breath, he rapped on the door.

A busty blonde opened the door, one that he recognized. She looked Oliver over with a smile. "Hey," she said, leaning against the doorway. "Come back for seconds?"

Out of the corner of his eye, he could see Tommy checking her out approvingly. "Uh, no," he replied quickly. "Actually, I'm here to see Felicity."

She scoffed at him. "Why?"

Oliver clenched his jaw. "Is she here?"

She rolled her eyes at him and turned away. She spoke to someone inside. "You have a visitor."

Tommy slapped Oliver's arm, staring at him. "You hit that?" he mouthed.

"Shut up," he whispered through clenched teeth.

Felicity showed up at the door and looked at both of them in surprise. "Oh, hi." She looked at Tommy, and then back at Oliver. "A friend of yours?"

Oliver smiled. "Yeah. This is—"

"Ah!" she interrupted. "Why mess with a good thing?" She looked at Tommy again. "I'll just call you…the cute one."

Tommy grinned at her and laughed. "What?"

"Oh, he didn't tell you?" She tilted her head at Oliver. "I call him Pretty Boy."

Tommy looked at Oliver with a wide grin. He looked back at Felicity. "So, he's pretty and I'm cute?"

She shrugged. "Sure, why not."

Tommy extended his hand. "Well, it's very nice to meet you. May I call you gorgeous?"

She shook his hand and rolled her eyes. "Oh my god, did you both go to the same lame charm school?"

Tommy raised his eyebrows in surprise. "Is this how you talk to all the guys?"

"Aw, worried that you're off your game?" she teased. "Here's a tip. Lines don't work. Not on real women."

He laughed out loud. "Wow. You're incredible."

She shook her head. "See, this is why I weep for future generations. I insult you and you're impressed? Somewhere in your past, somebody crossed the wires."

He stared at her, and then looked at Oliver. He shook his head, reeling from the conversation. "I'm gonna wait in the limo." He turned back to Felicity. "It was a pleasure meeting you, Felicity. And I can promise you, that isn't a line." He winked at her, patted Oliver on the shoulder, and walked away.

She looked at Oliver, impressed. "A limo, huh? So I was right about the rich kid thing."

Suddenly being alone with her brought back all the butterflies. "Yeah," Oliver said breathlessly. "Can I talk to you? Privately?"

"Uh, okay," she said tentatively. She stepped out of the room and closed the door behind her. "There's a common room at the end of the hall, it might be empty."

He just nodded and followed her lead.

The room was indeed empty, and they sat on a couch in the far corner. He rubbed his hands on his trousers, taking a deep breath. "So," he began, "I thought a lot about what you said, and I decided that I'm dropping out."

"Oh!" she replied, wide eyed with surprise. Did he detect a hint of disappointment? "That's…that's good, right?"

He took another deep breath. "We'll see. I still have to face my parents. There's no telling how that's going to go."

"Still," she encouraged, "it's a big step. You're taking charge of your own life."

He looked down at his hands. "Yeah," he replied softly.

"Hey." She placed her hand under his chin and lifted his head. "Why the sad face?"

He shrugged. "I'm just glad I met you, and I'm sad that I have to leave."

She smiled at him. "Well, that's the way these things happen sometimes. People come and go in our lives. Some stay for a while, others pass through in an instant. We can't hold onto the ones that pass through, because they're meant to be ephemeral."

"How can you tell the difference?"

She shrugged. "Time, I guess? I don't know. I don't have the answer for everything," she added with a giggle.

He laughed. "Could have fooled me." He looked down at his hands. Something Tommy said just occurred to him. He looked back up at her. "Do you believe in fate?"

She looked distantly at a point past his shoulder, thinking about his question. "I think that there are some things that can't be explained as a coincidence, but at the same time I believe we choose our own fate. So, yes and no?"

He smiled. "I guess what I mean is, if two people were meant for each other, do you think fate would bring them together when they're ready?"

She shrugged. "Who knows? I don't know. Maybe? Sounds like a romantic idea."

"That's what my friend calls me—the romantic."

"Does he, now?" she teased.

Oliver shrugged. "I don't know. The thought comforts me a little." He looked at her meaningfully.

She smiled warmly at him. "Well, like I said. Who knows?"

He nodded, and stood up reluctantly. She stood up with him. "I should get going," he said.

"Okay," she replied. She stepped forward and wrapped her arms around him, surprising him with her affection. He swallowed the lump that formed in his throat and wrapped his arms around her. Please let me see her again, he prayed helplessly to whatever deity would listen.

"Take care of yourself, Pretty Boy," she murmured.

He laughed. "Are you still not going to ask for my name?"

She released him from the hug and looked up at him with laughter in her eyes. "Tell you what. Next time you see me, you can tell me your name."

He laughed again and nodded. "It's a deal."

Before he could talk himself out of it, he swiftly bent down and kissed her on the lips. He pulled away just as quickly, and saw her blushing slightly and biting both lips. He gave her a cheeky wink before turning around and walking to the door. He stopped one more time and looked back at her.

"See you around, Felicity Smoak." And with that, he left the room with hope in his heart.

A/N: I may have lied about how many chapters are left. Well, maybe not. But I think there will be a short interlude before the 1x03 rewrite, because Tommy and Oliver are still talking to each other in my head, and they won't shut up until I write it down. (Plus I miss Tommy and he's so much fun to write.)