This is a response to the request I got for Killian to have a conversation with young Emma, hopefully I did it justice! The conversation just kind of steered itself. The hardest part was 1. figuring out the situation, before or after Killian has met Emma? and 2. How on earth am I going to get Killian to time travel and/or realm hop? So, of course, this is completely made up, set during the time when Rumple had Killian's heart.

26. Orphan

It's a bad time when the Dark One has your heart. It usually means you end up doing things you don't really want to.

Like time traveling.

After that one time going through Zelena's portal, Killian had sworn off time travel, and, unless it was absolutely necessary, realm hopping.

So what was he doing? Time traveling.

"Your task, Pirate," Gold had sneered, "is simple. Get on the bus. Find the Apprentice. Watch what he does and where he goes. Understand?"

With gritted teeth, Killian had nodded, knowing that even if he didn't understand, it wouldn't matter; he was not in full control of his actions.

Which was how, an hour later, he ended up about twenty years in the past, across the street from a bus stop in the great state of wherever the hell he was. He didn't get the luxury of specifics. All he knew was that if he followed the girl with dark hair, he'd be on the right bus.

And there she was, sitting with a blonde.

A blonde he would recognize anywhere, no matter the realm or time.

And his suspicions were confirmed when he heard her name: Emma.

No wonder Gold had left out specifics.

He watched as the blonde stormed off down the sidewalk before turning a corner, leaving the brunette on her own at the stop.

Just a few words, Killian thought to himself, she'd barely remember it. There was an uncomfortable tug in his chest that he knew was from Gold in control of his heart, but he was still able to go after Emma, so he at least had some time left. Walking at a brisk pace, it was only a few seconds before he rounded the corner and found her. She was a good distance away, but even then he was able to tell what she was doing: picking the lock on that door.

And he had to hand it to her, after she saw him, she seemed very relaxed as she turned from the door and leaned against the wall of the building, as if she hadn't been doing anything. She looked down, arms crossed, appearing not to pay him any attention.

"Hi," he said.

Her head immediately snapped up, eyes wide and wary.

He felt the need to smack himself in the head. No matter how friendly he made his voice, a guy dressed in black on the side of the road was creepy. Nicely done, Killian. Seeing as the other first time he met Emma Swan had been when she'd found him cowering under a pile of bodies and subsequently tied him to a tree, he was zero for two on good first impressions.

"Sorry, didn't mean to startle you," he recovered quickly. "Do you happen to have the time?"

"Quarter to ten," she replied, though since she hadn't looked anywhere, he wasn't sure if she was telling the truth or had simply spouted an answer to make him go away.

"Right, thanks...Any idea when the next bus comes?"

This time, she turned to him slowly, eyebrows slightly raised, and utterly unimpressed. "Bus stop is around the corner. You aren't from around here." There was no question in her voice.

"That obvious?"

She snickered a bit. "You don't have the right accent for Minnesota."

"I do have the lock picking skills, though."

Suspicion clouded her features, but even after concluding he wasn't a cop she didn't lose an ounce of that famous Swan attitude he knew too well. "Gonna scold me for trying to break in?"

This time he was the one to laugh. "Hardly, Lass. Me reprimanding you for lock picking would be of the highest forms of hypocrisy."

"So you can pick locks?" She said the words, testing them out. With one eyebrow raised, she sized him up again, then shrugged, seeming to buy it.

"Please," he said. "I've been picking locks for longer than you've been alive." About three hundred years longer, but that was beside the point. "You develop a special range of skills as an orphan." Or pirate, but, again, beside the point.

He winced, the tug in his chest from his orders suddenly starting to become painful.

Emma didn't seem to notice; her head was turned towards him, but her eyes were not focused on anything near her. "You're an orphan too." Her voice had gone quiet. "It just..never hit me before. No matter how old you are, you'll always be an orphan."

Seeing the dejection on her face, hearing it in her voice, Killian was determined to speak to her for just a little longer. "It'll feel like that," he admitted,. "For quite some time, like you can't get to know anyone and trust doesn't exist, and if it does it isn't worth a damn."

He realized she was looking at him expectantly, bright eyes so young, but not unfamiliar with betrayal and pain. "And then what?"

She needed that answer, even as he felt himself being pulled away from her. "And then you find your family. They might not be blood, but they'll be the ones who stay no matter how many times you try to push them away. Or screw up," he added ruefully.

At least he succeeded in getting a grin out of her. "You found yours?"

"Found, didn't realize, lost, found again." He rubbed the back of his neck. "Did that a few times, actually, but they aren't counting. And you always find your way back home. You'd be surprised how stubborn that pull can be."

Annoyingly strong, sometimes. But not quite as bad as the Dark One's pull, which forced him to turn away from her.

"Heading out?" she asked, eyeing his rather sudden, jerky movement.

He nodded. "Aye, Lass, I believe I have a bus to catch. But you take care of yourself."

He wanted to stay. He wanted to stay with all his heart.

"And by the way," he called, turning around and taking steps backward. He saw her head turn. "A little less elbow, a little more wrist for that door."

But that heart wasn't with him, and it was forcing him to walk away and round the corner.

I know that if you want to get technical, Killian isn't really an orphan, but I still feel that with what we know about his past and his father and losing Liam, he had to do a lot of growing up and taking care of himself.

But anyway, I hope this was a good one! As always, I love to hear feedback and I'm always up for requests