A/N: This idea came to me completely out of left field but I thought that it would be fun to write. I've listened to two songs a lot in the past couple of days. 500 Miles, which I never realized was so romantic until Sleeping At Last covered it, and the song this fic is named after by La Rocca.

I watched every Jackson and April scene since 8x21 and most of the Jackson and Stephanie scenes before I wrote this so enjoy! : )

Disclaimer: I do not own Grey's or any of the movies and songs mentioned in this fic.

"People think dreams aren't real just because they aren't made of matter, of particles. Dreams are real. But they are made of viewpoints, of images, of memories and puns and lost hopes."

― Neil Gaiman

Jackson lay on a bed next to Stephanie and stared at the on-call room ceiling. She was fast asleep but he was having a hard time closing his eyes. The storm was already hitting Seattle hard and there was still so much left to do. It was best to be over prepared in these kinds of situations but Hunt had advised him to take a nap and get some rest before things got worse.

But he couldn't fall asleep because he couldn't get that stupid song out of his head.

"I would walk 500 miles and I would walk 500 more," he quietly sang to himself.

He had been singing The Proclaimers' tune ever since Matthew Taylor's spontaneous flashmob proposal. He couldn't seem to stop thinking about that moment, and he couldn't stop singing that song.

He rolled over onto his side and closed his eyes as he felt his lids become heavy.

"When I'm dreaming yes I know I'm gonna dream, dream about the time when I'm with you."

Jackson found himself wandering the hospital hallways. He was wearing the same clothes that he had worn to work, black jeans and a white t-shirt with a pair of Air Jordans. He continued walking down the hallway even though everything was eerily quiet. There was no one else around and something was definitely wrong. He spotted a tall figure in residents' scrubs walking towards him and he froze.

He knew where he was now and he didn't want to be here.

He hadn't had this nightmare in years.

The face of the figure came into focus and as he expected, it was Charles staring back at him.

Normally this was the part when the dream would get gory, frightening, and hopeless, and he would wake up screaming. But instead, Charles just smiled at him.

"Hey buddy, it's good to see you. You're the big man on campus now, congratulations," he grinned. "And I must say, those attending scrubs look fantastic on you."

Jackson chuckled but looked around in confusion. "What is going on? This isn't how this dream usually goes." He furrowed his brow and stared at Charles. "I mean, obviously this is a dream, right?"

"Why? Because I've been dead for three years?" Charles joked. "Yeah, it's a dream, but that doesn't mean it's not real. I am here to take you on a journey."

Jackson shook his head as he attempted to make sense of the situation. He had never had a dream this weird. "A journey? So, is this like It's A Wonderful Life? Are you struggling to get your wings?" He questioned sarcastically.

Charles reached out and punched him in the shoulder. "No, smartass, this is all about showing you something. But I am an angel," he added smugly.

"Showing me what?" Jackson asked in annoyance.

"Let's begin and you'll see," Charles grinned.

There was a bright flash of light that forced Jackson to close his eyes, and when he reopened them, he was no longer standing in a hallway of Grey-Sloan Memorial Hospital.

He looked around curiously before recognition set in. "We're at Mercy West."

"Yup," Charles answered quickly. "We're at Mercy West Medical Center and its July 1st, 2007."

Jackson turned to him in alarm. "Are you serious? That was the first day of our internship."

"I know," Charles smirked. "And the person we're waiting for will walk through the doors any second now."

Jackson turned towards the doors of the main entrance and waited in intrigue. Minutes later, a petite brunette with shoulder length hair walked into the hospital. He couldn't help but smile to himself. She had changed so much.

"April," he breathed.

"Yeah," Charles answered as he pointed towards the door. "And there you are."

Jackson laughed as he followed his past self towards the main set of elevators. He had been so much skinnier back then, and so clean shaven. "This is crazy," he muttered incredulously to himself. Charles pushed him inside the elevator that was already being occupied by the 2007 versions of April and himself. "They can't see or hear us right," he whispered.

Charles laughed boisterously, "Of course not!"

Jackson carefully observed April as she avoided eye contact with him…the other him. He had almost forgotten how shy she had been. But she had been an exceptional surgical intern, the star of their class by a mile. She had always been prepared, had known the answer to every question, and had possessed a boundless amount of energy. She had been annoying but sort of charming and endearing.

"So why are we here?" He finally asked Charles.

"Unbeknownst to the both of you, and although you didn't have your first real conversation until two days after this, April was the first person that you met in Seattle. It was kismet."

Jackson rolled his eyes. "Wait! So that's what this so called journey is supposed to be about? I don't believe in soul mates. I don't believe in fate. I don't even know if I believe in God, or heaven, or anything like that."

Charles shrugged. "I don't make the rules, I just follow them."

Jackson screwed up his face in puzzlement but Charles spoke again before he could formulate a question.

"So you don't think that April Kepner plays a special role in your life?"

"I never said that," Jackson corrected him. "I said—"

"Can it, Avery," Charles interrupted him. "Let's fast forward a few months."

There was another bright flash before Jackson found himself in April and Reed's old apartment. He barely remembered their place even though he had spent countless hours there. He was ashamed to realize that he had locked away his time at Mercy West. He barely reflected on anything pre-Seattle Grace and he knew that it made him a terrible, ungrateful person. He knew that April visited Charles and Reed's graves on birthdays and anniversaries, but he didn't even do that.

A familiar blur caught his attention and he turned to Charles in confusion. "Did I just sneak out of April and Reed's apartment?"

His burly friend looked at him in disbelief. "You seriously don't remember this?"

Charles grabbed his elbow and pulled him into the kitchen. Once again, he couldn't stop himself from smiling at the image of a younger April. She wasn't sexy in the way that she was now, but she was still really cute. She was wearing a flannel pajama set and her hair was pulled up into a messy bun. His smile dropped when he noticed that she looked upset.

"What's wrong?" He questioned in concern. "Why is she crying?"

Charles didn't answer his question and stared at the doorway to the kitchen. Eventually, Reed entered the kitchen with a guilty expression on her face and everything fell into place for Jackson. Now he knew why Charles had brought him to this moment.

"This is the morning after my one night stand with Reed."

"Still don't know if I've forgiven you for that by the way," Charles commented casually.

"And I ran into April in the bathroom before I could leave," he continued.

Jackson stepped forward and listened to the conversation with heightened interest.

"April," Reed spoke softly. "Are you okay?"

"Yeah, I'm fine," April squeaked.

"I-I had no idea," Reed stuttered. "I didn't know that you had feelings for him or otherwise I wouldn't have…I'm so sorry."

"Wait, what?" Jackson mumbled to himself. April had had feelings for him during their time as interns?

April shook her head and meekly met Reed's gaze. "It's okay; it's not a big deal."

"It is a big deal," Reed argued passionately. "Why don't you just ask him out? Why don't you tell him?"

April's eyes widened and she stared at her friend in alarm. "Are you kidding? Have you seen him?"

"I don't know why all the women at Mercy West thought you were some kinda god," Charles chirped snidely.

Jackson raised his hand to shush him. Even though this conversation had taken place six years ago, it was important to him. All of this was completely new information for him.

"Just ask him out for drinks or something," Reed continued to pressure her. "Start small."

Jackson ran a hand over his head and groaned while Charles smiled knowingly. "You remember what happened a few days from this point, don't you?"

"Yeah," he sighed. "April asked me to go for drinks, and I said no."

"Because you had post-ops to monitor," Charles supplied.

"But I did have post-ops to monitor!"

"I know that, but she didn't, and she never got the courage to make a move on you again until…"

That annoying flash of light changed the scenery once again and they now stood outside of a San Francisco hotel room. Jackson already knew that this moment was significant; it had unknowingly changed his life. He recognized its momentous weight all on his own but Charles obviously felt that it was worth a revisit.

Charles whistled as they watched the couple in front of them kiss for the first time. "You're putting up a real fight here, bud," he jabbed.

"Shut up," Jackson muttered. "Look at her," he argued weakly as he gestured towards April. A year later and he was still completely enamoured. She looked incredible and her confidence that night had been so sexy.

Everything about her that night had been sexy. He had never been able to say no to her, and that night had seen the same result, except for an entirely different set of reasons. Up until that moment…this moment that they were watching right now…he had never realized how attracted he really was to his best friend.

"Question," Charles began curiously. "Why did you do it?"

"Look at her!" He repeated loudly. At that moment April had her arms draped across his shoulders and she was kissing him passionately. She had really surprised him by how good of a kisser she had been for someone with so little experience. Actually, she had been freakishly good at every aspect of sex. "And I thought that it would be good for her to let go," he added after a moment of thought. "I didn't know about her and Jesus then."

Charles scoffed, "Man, I'm dead; you can be honest with me. You did it because you didn't think that it would affect you. You never thought that your dorky, average looking best friend would get under your skin."

Jackson couldn't help but take offense to that comment. "First of all, April is not average looking, she's gorgeous, and that's not true at all!"

"Yes, it is, don't argue with an angel," he scolded. "You did it because you didn't see it having any long-term consequences for you. You never thought that you would fall in love with her."

Jackson took a step backward as he heard the hotel room door close. "Whoa, who says I'm in love with her. I never said that."

Charles laughed as he placed both of his hands on Jackson's shoulders. "Still in denial, I see. It's time for us to move on."

Their new location was Joe's and Jackson quickly found a past version of himself standing in the middle of bar, looking around with a frown on his face. This was the day that Sloan had slipped into a coma. It was also the day that April had left Seattle to go back home. It had been a horrible day.

Jackson swallowed harshly before he spoke. "I know what this is and I don't want to be here."

Charles nodded solemnly. "I know, but this is an important moment."

"She left," he murmured, "and she left without saying goodbye. I was pissed and I was hurt," he confessed. He turned to Charles and spoke angrily, "Okay, I'll admit it, she hurt me. Are you happy now?"

Charles stared at his friend sadly. "I'm not happy; I'm just trying to make you see."

"Make me see what?" Jackson cried in frustration.

Charles ignored his questioned and continued. "So she left, is that why when you two finally got together you had to leave first? Because you were afraid of her leaving again?"

"What are you talking about?" Jackson asked in confusion.

"The pregnancy scare," Charles explained. "You ran. You dumped her. You broke her heart."

"What?" He questioned with a mixture of disbelief and anger. "I was ready. I told her I had feelings for her. I freakin' proposed! She broke my heart first!" He finally exploded.

Charles grinned triumphantly as he threw his hands in the air. "Yes, progress!"

Jackson opened his mouth to speak but he covered his eyes when there was another flash of bright light.

They were now standing in the hospital parking lot directly in front of a familiar car with steamed up windows. Jackson coughed uncomfortably and scratched his head. It was unmistakably the evening of Bailey's wedding.

"This is one of my all-time favourite Jackson Avery douchebag moments," Charles stated mischievously.

"Hey! You're a shitty angel!" Jackson shot defensively. "I'm not that bad." At least he hadn't acted like Karev and slept with multiple women. He had only ever been with one intern.

"No, you're not," Charles conceded. "Lots of attendings sleep with interns but not a lot of attendings sleep with interns just so they can forget about their ex." He turned to the other man with a knowing grin. "You didn't even want to take her to the wedding, but you just couldn't stop thinking about April in that strapless dress."

Jackson sighed heavily and looked down at his shoes. Charles' statement was completely true but it sounded absolutely horrible when it was said aloud. "It may have started out like that," he began slowly. Stephanie had been a distraction, a coping mechanism, but things were different now. "But Steph is a great girl. She's smart and funny, and fun. She's great," he repeated.

"She is great, but is she great for you?" Charles posed. "Sure, things are light and fun now but she's going to want more soon and I don't think that's what you want, at least not with her."

Their next location was the OR and he and Stephanie were performing a rhinoplasty. He wasn't sure what was significant about this moment in time. They had done dozens of rhinoplasties together.

However, once he listened to the conversation they were having, he realized why Charles had brought him here.

"You never know, we could end up somewhere near each other, it wouldn't be the worst thing in the world."

He turned to Charles in exasperation. "So? What was wrong with that? I know that you're going to tell me."

Charles chuckled, "You're right; I am going to tell you. There would be nothing wrong with what you just said to her except for the fact that a few days before this you said to April, and I quote, 'Let him get to know you better. Once he does he's gonna wanna follow you anywhere'. You also didn't want to leave her for Tulane. See the difference? I don't have to spell this out for you, do I mere mortal?"

Jackson groaned as he ran a hand over his face. "Yeah, I get it," he muttered, "but I think that you're reading too much into this."

"Hey, you're the one saying these things, not me." He paused before he stated, "I think that it's time we go back to the present day."

There was another flash of light and before Jackson could see anything he heard the same song that he had been singing all day. Charles had brought him back to the moment of Matthew's proposal to April.

Charles found Jackson in the crowd and asked, "What's with your face?"

"I'm smiling you idiot," Jackson retorted. "How can I not?" He pointed towards April and said, "Look at how happy she looks. How can I not be happy for her? Isn't that how a good person is supposed to act when their best friend's boyfriend asks her to marry him?"

Charles smirked while shaking his head. "Not when the relationship is one like yours and April's. You aren't able to stay away from each other. Feelings are still there, it's so easy to tell. How many times have you thought about kissing her since you broke up?" He pestered.

Jackson knew the answer to that question and it was too many. But he knew why he and April hadn't worked and that wasn't going to change. "I was just this mistake she kept making," he said bitterly. "I was dessert. She called me a car crash!"

"You never exactly did anything to help her see things differently," Charles quipped. The plastic surgeon narrowed his eyes angrily but he trudged forward. "She misses you and she misses sex, but you moved on. You saw how much you hurt her when you told her you were sleeping with the intern. You wanna know why she wants to marry that guy?" He questioned as he gestured towards the dancing paramedic. "Because he's honest with her, he tells her how beautiful he thinks she is and how much he loves her, and we both know that a man has never said those things to her before. And she thinks that this guy wants to marry her for those reasons and those reasons alone, not because he thinks she's pregnant."

Jackson bit down on his bottom lip and nodded as he watched Matthew get down on one knee. April's biggest fear was that she would end up alone…that no one would ever love her. Matthew was the first guy to express those feelings towards her so of course she would be ecstatic about marrying him. He adored her and he made her happy. And that's all Jackson really wanted.

"I love her, I just want her to be happy," he stated sincerely.

"So you finally admit it? You love her?"

Jackson nodded and whispered, "Yeah, of course I do."

Charles clapped his hands together and declared. "I think you're ready to see the future now."

Before anything could happen, Jackson placed his hand on Charles' shoulder and asked, "Can you not do that blinding light thing again?"

"No way, it's cool," Charles laughed.

Jackson sighed before he closed his eyes. When he reopened them, he observed his new surroundings very carefully. They were standing in a non-descript, white bathroom, probably one belonging to a hotel, and April was the only person in the room.

Charles was right; he had been in denial about how deep his feelings for April truly ran. But what he couldn't deny was the feeling of relief and overwhelming happiness as he took in the image before him. April was standing in front of a bathroom mirror wearing a short, midnight blue, silk nightgown. She was part of his future and there was a wedding ring on her finger. They were married.

"She looks incredible," he whispered as he walked up to her. She had an irrepressible smile on her face as she fidgeted with her hair. "She seems nervous."

"Of course she's nervous," Charles replied. "It's her wedding night."

Jackson couldn't stop the grin from spreading across his face. Maybe he had given her the wedding that she had always wanted. In a field with butterflies.

After taking a deep breath she walked towards the door and he followed her. To his shock, he wasn't the one waiting in the bedroom for her. Matthew Taylor was the one excitedly sitting on the edge of the bed.

"Wow," the geeky paramedic gulped. "You look unbelievable."

April blushed and shyly answered. "Thank you."

Jackson turned away from the scene and angrily narrowed his eyes at Charles. "You said that this was my future."

"No, I said it was the future," he corrected. "Matthew and April are married. You're still her friend but not really, not like you used to be."

"I wanna see my future," Jackson demanded through gritted teeth.

Charles sighed, "Okay, as you wish."

Another flash of light changed the scene from a hotel room to a conference room at Grey-Sloan Memorial. Jackson saw himself sat at the large table, alone, surrounded by a mountain of paperwork.

"This is it?" He asked glumly.

"Yeah," Charles answered regretfully. "You bury yourself in your work. You barely even go home anymore."

Jackson swallowed harshly before he asked, "What about Stephanie?"

"She eventually got fed up and broke it off. She's with Shane Ross now, she's happy," Charles stated matter-of-factly.

Jackson was glad that she was happy and he could see Ross treating her well. Stephanie had been right when she had yelled at him at Joe's, she did deserve to be treated better. He was doing a pretty poor job of that. "And what about April?" He inquired nervously. "She's really happy with Matthew?"

"He treats her like gold."

"Of course he does," Jackson said quietly to himself. And he really did just want her to be happy. He stepped closer to the conference room table and leaned down until he was eye level with his future self. He looked exhausted and miserable.

This was a freakin' horrible future.

Charles could sense Jackson's discomfort so he spoke up. "I can show you something else, if you want." Jackson raised an eyebrow in curiosity. "It's a future scenario where both you and April are happy."

"I wanna see it," he answered quickly.

"Okay," Charles smiled.

He switched the scene and Jackson found himself standing in the living room of a nice house. It wasn't anything fancy but it was definitely upper-middle-class, and it was most certainly a family home. He could see a nice yard through the window and an SUV parked in the driveway. He heard a baby cry from somewhere in the house and he felt compelled to follow the noise.

He ran down the hallway and stopped in an open doorway. His breath hitched and he felt an overwhelming surge of emotion as he stared at himself sitting in a rocking chair with a baby in his arms. His future self was wearing only a pair of boxers and he was cooing to the tiny human. He was also wearing a wedding band.

Jackson turned his head when he heard footsteps heading his way. His heart started to beat a little faster in his chest when he saw April sleepily walking towards him, wearing one of his favourite t-shirts. Even though he was a ghost or a spectral, or whatever, he still moved out of the way so that April could take his place in the doorway.

But he did lean in to savour the familiar smell of her hair.

"Jackson, what are you doing?" She asked with a soft giggle. "You're spoiling her."

The Jackson sitting in the rocking chair glanced up at the red-head with a happy grin. "I can't help it. She's so perfect."

"If you keep doing this then she's never going to fall asleep unless one of us is holding her," April stated as she weakly attempted to reprimand him.

"She's got me wrapped around her finger already. I wonder where she learned how to do that?" He asked with a teasing note to his voice.

April rolled her eyes and ignored him. "Put her down in her crib and come back to bed."

After a moment, he did as he was told and placed the baby girl in her crib. "I love you. Sweet dreams," he whispered. He walked up to April and wrapped his arms around her waist. "When can we make another one of those?" He asked with a bright smile.

April laughed quietly as she grabbed his hand and led him out of the nursery. "Not yet…but we can practice," she added with a wink.

Jackson growled playfully as he chased her into the bedroom.

The couple disappeared and Charles watched his friend take it all in in silence. He could tell the usually well put together guy was having a difficult time keeping his composure.

"I could have that?" He finally asked and he could hear the waver in his own voice.

"Yeah," Charles replied truthfully. "It won't be easy, things with Matthew and Stephanie will be messy, but eventually you'll have this. April as your wife. The house. The baby. You just have to be honest."

"Honest about what?" He questioned in confusion.

"Everything," the angel answered cryptically. "Just stop repeating your past mistakes. Right now you're trying to pretend that you and April never happened. Remember how upset you were when she tried to do that? And you should have told her how you really felt when you asked her to get married but you never had the guts, and believe me, man, you don't want to regret not telling the woman you love that you love her."

Jackson's throat constricted. He had known, probably better than anyone, how much Charles had loved Reed. "I'm sorry about Reed, I—"

Charles quickly shook his head and interrupted him. "This isn't about me, it's about you. The universe doesn't bring people together for no reason, that's what I've been trying to show you. April knows that, and when she was talking about the universe pulling two people together, she was talking about you; you just refused to see it." Charles began to slowly walk backwards. "Just be honest. Don't be afraid to put yourself out there." Charles grinned as he added, "When you love someone you say it, I was told to remind you of that."

"Mark," Jackson whispered to himself before taking a step forward. Charles was moving away from him and he wasn't sure why. "Wait! Charles! What do I say? I've never done this before!"

"Just be honest," he repeated.

"Wait!" Jackson yelled, but it was already too late. Charles had vanished.

Jackson awoke with a start and shot up into a sitting position. He squeezed his eyes shut as he tried to calm his uneven breathing and hammering heart.

He heard movement beside him and Stephanie sleepily murmured, "What's wrong? Did you get paged?"

He slowly shook his head. "No…I-I just had a dream…a really weird dream."

Stephanie laughed, "Was it at least a good one?"

He swung his legs over the side of the bed and ran both of his hands over his face. "Yeah," he answered after a minute of silence. "Well, the ending was anyway. I wish it had been real."

"...Dreams come to tell us something about our lives that we are missing."

― James Redfield, The Celestine Prophecy

A/N: Please leave a review! And let's hope the finale is kind to us (unrealistic wish lol).