Killian watched Bellamy and Octavia walk up to their apartment building and go through the door before he pulled away from the curb. He always did this, needing to make sure both of them got home safe and sound before he felt ready to leave. On his drive back to his apartment Killian thought back on the dinner they had shared with Emma and Clarke, he remembered the way Emma laughed and smiled and the cute way she tried to use chopsticks. It seemed almost too good to be true that they would run into each other like this, Killian didn't necessarily believe in fate or destiny but it seemed almost too much to be a coincidence. He parked his car in the garage and walked up to his apartment, greeted by his many houseplants. Killian was filling a jug so that he could water them when he felt his phone vibrating in his pocket, he fished it out and felt his stomach lurch when he saw it was a text from Emma.

E: "Your little brother definitely has a crush on my little sister."

Killian chuckled as he typed out a response, "Oh and how are you so sure?"

E: "Did you not see the way they were making eyes at each other all night?"

K: "True, and I don't believe it was merely coincidence that we ran into each other tonight. I would say your little sister is as infatuated with my little brother as he is with her."

E: "Do you always talk like you stepped out of a Jane Austin novel?"

K: "My extensive vocabulary isn't the topic of our conversation now is it? Now what do we do with this information?"

E: "Well we could be evil and tease them about their budding romance... but I think I have a better idea."

K: "Oh and what is it?"

E: "Best said in person, don't want to leave a paper trail. Do you want to meet for some coffee so we can talk?"

K: "Coffee sounds great. There's a place around the corner from me that also has great pancakes, if you would like to join me for breakfast there tomorrow?"

Killian held his breath as the little dots appeared on his phone as she typed out her response, this would be their first time alone together since the concert that she ran out of. He hoped he hadn't been too presumptuous in asking her to have breakfast with him. His phone pinged when her response came in, Killian took a deep breath and read her message.

E: "I like pancakes, text me the address and I'll meet you at 10 tomorrow?"

Killian sighed in relief and smiled as he typed his response, agreeing to meet her at the coffee shop. He wondered what her idea could possibly be and if it had anything to do with the look she gave him after she read her fortune, the way her cheeks reddened in a way that had nothing to do with the work out she had finished. Killian flopped onto his bed and tried to fall asleep but visions of Emma kept running through his mind.

His eyes snapped open when his alarm started blaring, pulling him out of a very nice dream involving Emma, some chopsticks, and sushi. He groaned and rolled over, swiping his thumb across his phone screen and shutting off his alarm. Killian forced himself out of bed and put on his running shoes, preparing for his morning jog down to the harbor, afterwards hopping into the shower. He tried to keep cool about breakfast with Emma and he most certainly didn't pick the blue button down shirt that Belle said made his eyes pop nor did he stand in the mirror for 15 minutes trying to get his hair perfectly disheveled. He sighed at his reflection before grabbing his wallet and keys before rushing out the door to get to the cafe. Killian walked up to the cafe spotting Emma sitting outside on the patio, a mug of hot chocolate sitting in front of her.

"Been waiting long love?" he asked as he sat down.

"No, just a few minutes," she answered, "So are you dying to hear my brilliant plan?"

"Oh so it's a plan now? Last night it was just an idea," he smirked.

"I had some time to turn it into a plan," Emma said with a small smile and a sip of her cocoa.

"Well let's hear it then love!" Killian said leaning back in his chair.

"Before I do, I just need to know something," Emma leaned forward, a serious look in her eye. "Bellamy, he's a good kid right? He won't hurt or betray anyone?"

"Of course, Bellamy's a great lad," Killian said, Emma stared back at him, still looking unsure. "Look once Bellamy decides he cares about someone, he cares with his whole heart. He cares more about Octavia and her well being and happiness than his own. He's even helped me through a rough patch and that's how I knew he truly cared about me."

"Okay, I believe you and now I'm even more confident about this plan I've been hatching," Emma nodded.

"Well do tell love, I'll admit I'm very curious to know now that you've been talking it up," Killian encouraged.

"I think we should try getting Bellamy and Clarke together," Emma announced.

"Wait what?" Killian raised both brows in disbelief.

"Hear me out, I'm not saying we pimp out our little brother and sister. But if we maybe give them the opportunity to hang out together something might happen between them," Emma explained.

"Okay but can we even do this? As mentors?" Killian asked.

"I looked at the handbook last night and there's no rule expressly saying we can't," Emma smirked, "Look all we have to do is just give them a chance to hang out together, if there's a spark then they can take it from there and if not then at least we tried."

"It's not a half bad plan but just explain why you are so intent on this?" he questioned.

"Clarke got put through the ringer last year, she deserves some happiness. And Bellamy makes her smile like nothing else, she practically lit up when she saw him at the restaurant last night. She at least deserves a shot at happiness," Emma said her eyes on the table instead of on Killian. Killian sat there mulling over Emma's words and leaned in, his forearms resting on the table and made sure Emma was look at him before he spoke.

"I think this is brilliant Swan," he said when her eyes met his, "The only question is what do the youth these days do for dates?"

"Good question," Emma laughed, "I was hoping you would know Mr. Cool Radio DJ."

"You think I'm cool?" Killian asked a bit surprised.

"Well at least in the know of what is cool, so any ideas on something that's fun and not lame and somewhat appropriate for a seventeen year old and a nineteen year old and where we won't stick out like sore thumbs?" Emma took a sip of her hot cocoa, getting a small bit of whipped cream on the tip of her nose.

"Umm bowling? A movie? There's a rock climbing place around here that I here is pretty fun. And you have a little cream on your face," he said taking a sip of his coffee.

"Really where?" she said wiping her cheek, "Did I get it?"

"No love, here let me," he leaned forward and swiped his thumb across the tip of her nose, he felt shockwaves travel up his arm and his breath catch in his chest. He looked up and she was looking at him with the same expression as when she read her fortune cookie. "Got it," he breathed out, sitting back in his seat.

"Thank you," Emma said just as breathlessly. "Um so no to rock climbing, I can't do heights," she shook her head.

"A concert perhaps?" Killian suggested before he saw her visibly stiffen in her seat, "Never mind." He added quickly, remembering how disastrously the Hozier concert had turned out, "Um, you know that old movie theater on Mass Ave?"

"Yeah?"

"Well I hear they're holding a screening of The Princess Bride there next weekend, that could be fun. I mean who doesn't love that movie?" Killian asked.

"That's actually a great idea," Emma said looking surprised.

"Surprised love?"

"Would you be offended if I said yes?"

"Only slightly, now I'm starving so how about we order some pancakes and we hash out the details?" he said catching the eye of a waitress and waving her over.

"So are you a regular short stack kind of guy or do you go for the works, berries, chocolate chips, and whipped cream?"

"Plain with maple syrup, goes well with the eggs and bacon that I get with it. You?"

"I don't eat pancakes unless they taste just like cake, so there's your answer," Emma smiled. The waitress took their orders and they were soon brought their food over to them.

"You weren't lying lass, you really go all out with your pancakes," Killian said as he dipped a piece of bacon in syrup.

"Yeah, go big or go home," she said as she sliced into her pancakes. The two of them started digging into their pancakes and discussing the finer details of trying to get their Littles together.

"So are we telling them straight up that the four of us are going to the movie, or do we just happen to run into each other in line for tickets?" Killian asked.

"I think we should ask them, like I would say to Clarke 'hey there's this thing that Killian is taking Bellamy to and would you like to go too?' because if we try to accidentally on purpose bump into each other Clarke and Bell will see right through us. They're smart kids," Emma explained.

"That they are, you know I think this could work. You're brilliant Swan," Killian smiled.

"Thank you, but don't go complimenting my genius just yet. We should at least see how the date goes first," Emma said.

"Date?"

"Uh for the kids, of course," Emma added quickly.

"Right, we are but humble chaperones," Killian smiled but Emma could see that it didn't quite meet his eyes.

"Exactly, but this was fun," Emma reassured him, "I'll text you when I ask Clarke about the movie."

"I look forward to it Swan," Killian said, "And to sharing a large popcorn with you during the movie."

"I can't wait," Emma smiled, meaning it. Killian smiled back at her, having to mentally tell himself that he was not the one going on a date. They finished their food and took their checks up to the counter to pay, Killian had offered but Emma insisted on paying for her own meal.

"Well I'll be seeing you around then," Killian said, unsure of what to do with his hands deciding to stuff them in him pockets.

"Yeah, I'm looking forward to it," Emma replied.

"Really?"

"Of course, The Princess Bride is one of my favorite movies," Emma said.

"Any others?" Killian asked hoping to get just a few more minutes of her time.

"You'll find out eventually, I'll see you around Killian," she smiled and walked back to her bug. Killian stood rooted in his spot, smiling softly as he watched her go and already counting down the days until he sees her again.