For those of you who read Chapter 1 when it first came out, sorry about the transitions, the original file had lines between scene shifts but somehow they got deleted. I just added them back. Anyway, enjoy the next chapter.

Chapter 2: Doubt

As she pulled up to the Viridian City Airport, Delia asked, "You're sure you have everything, sweetie?"

Ash smiled and nodded. "I think so. Anything I didn't bring I'm sure I can find in Alola somewhere," he replied.

The airport was bustling as usual, given how busy Viridian City was in general. There were dozens of cars lining the entrances to the main building, people and Pokemon everywhere saying hello and goodbye to their loved ones. Ash loved the airport. It was the place where a new adventure always started and ended, so naturally being there made him think about some of the fantastic memories he had in other regions of the world. And now, he was just about to make more of them.

"Isn't this exciting, Pikachu? It's been a while since we've been to a new place," Ash said, glancing at the Mouse Pokemon on his shoulder. "Pika pika!" Pikachu cheerfully replied.

"Okay, you only have half an hour to make it to the gate, so you better hurry along, now," Delia said, bringing in her son for a hug. "Stay safe, Ash. And don't forget to wash your underwear!"

Ash rolled his eyes and smiled at that old running joke. Suddenly, a whole new wave of memories came to his mind about his first few steps as a Pokemon trainer. I've come so far, he thought to himself. I've accomplished so much...I've put in years of training, and was rewarded with win after win. So why do I keep feeling like something's missing?

In the very back of his mind, he knew the answer to that question. But with so many years passed, it was difficult to think about something like that at the moment. Especially after his recent relationship with Misty ended.

Sometimes, he still thought about the red-haired, tomboyish Gym Leader. How could he not? She was the first person he met and befriended on his Pokemon journey, and she had been through so much with him. She was there when Ash captured a Pokemon for the first time. She celebrated his first victories as a Pokemon trainer with him, and was there to support him through his first losses. She stood by him through his league challenge in Kanto, and supported him in the Orange Islands as well. Then after that, they traveled through the Johto region together. It was safe to say that for a very long time, Misty had been his closest friend.

Of course, Brock was also there, and no one can forget how helpful Brock can be. There was a reason he became a Pokemon Doctor, after all. But it was different with Misty. Maybe it was because she was a girl, and that she had a mild crush on Ash way back then. Maybe it was simply because of their personalities. Ash didn't know for sure. Things did change, though, when Ash left for the other regions. Misty had her own responsibilities to attend to, and Ash couldn't stay in one place. At the end of their Johto journey, when Ash, Misty, and Brock were standing at the crossroads to say their farewells, both Ash and Misty could tell that they harbored unspoken feelings for each other; but they didn't say anything.

Not at the time, that is. They were too young, and they had other aspects of life to focus on. But a year after Ash had returned from Kalos, they admitted how they felt and became a couple. For a while after that, everything was great for them. They were happy together, and everyone else enjoyed seeing them together as well.

However, it wasn't too long before Ash started to have his doubts. Sure, he always had fun hanging out with Misty, and it was nice to have someone to call his girlfriend. But as time progressed, he realized that he couldn't stop thinking about someone else. It was painful, and it made him feel extremely guilty because he knew that at one point in his life, he truly did have feelings for Misty. Perhaps now the fire that had started their relationship simply did not have the fuel to keep burning. Whatever it was, eventually Misty caught on to it. She figured out that Ash was thinking about Serena, and was angry beyond words at first. However, it surprisingly didn't take her very long to accept it with grace and dignity, though she did have to end the relationship, which was understandable. The two childhood friends remained nothing more than friends from that point on.

The vast array of emotions Ash had experienced from all of this still lingered in his mind. This was another reason why he chose to travel to the Alola region; he needed a vacation.

"Serena dear, can I talk to you for a moment?" Grace cautiously asked as she knocked on the door to Serena's room.

A few seconds of silence passed. "Sure, come in," Serena replied.

Grace quietly opened the door and stepped inside. "My, this room is a mess," she remarked, observing the numerous items of clothing and candy wrappers littering the floor. "Just how much time do you spend in here?"

Serena sighed. "Did you come up just to criticize me?"

"Serena, this attitude needs to stop. I truly don't know what's going on with you, but what I do know is that it's obviously affecting your career. Just how do you expect to come out on top if you haven't been in the game for a year and you're lounging around everyday with hardly an hour of practice?" Grace said, her voice firm.

"I go out...sometimes," Serena replied. "I've been hanging out with Calem a lot, okay?"

"And yet you still seem so glum all the time. Is Calem a good boyfriend? Does he treat you well, Serena?" Grace inquired.

"Of course he does, mom. He's a nice person," Serena answered. "I've been with him for like six months now, don't you think I'd know by now whether or not he was a good boyfriend?"

Grace raised an eyebrow, sensing that something was just not right about all of this. "Well then explain your constant moodiness. I've been tolerating it, because I didn't want to impose, but quite frankly you're starting to be very disrespectful towards me and above all else, I'm getting very worried about you."

Serena sighed again. "I'm sorry, mom. I know you're just trying to help...but I'm telling you now that you won't be able to help me with what I'm dealing with," she said.

"Try me."

"Hey, Ash, how are you?"

"Hey, Clemont, I'm fine, thanks. I just wanted to let you know that I'm leaving now for the Alola region," Ash said.

"That's awesome! I'm actually planning on traveling there myself in a few months, I just need to finish building my private jet," Clemont replied.

"Oh wow, that sounds fancy," Ash said.

"Eh, it's really not, it actually looks like a piece of junk because I'm trying to keep my budget low. I have gotten it to fly, though!...after crashing it once or twice. Okay, maybe six times."

Ash laughed. "I can't believe a guy your age is actually able to build his own plane. Science is so amazing."

"Not as amazing as what you've done these past few years! I can't believe throughout this entire conversation you haven't talked about your six straight league wins, Ash! Like for real, Alola sure won't be ready for a champion like you on their shores!" Clemont said cheerfully.

Ash chuckled. "I can't be getting cocky now, though I am curious about how many people are gonna recognize me while I'm there," he said.

"I mean, you're gonna be at the beach half the time right? That means girls in swimsuits everywhere. Do you understand how lucky you are?"

Suddenly Ash was reminded of why he was calling in the first place. "Hey, uh, have you seen Serena at all, by any chance?" he asked as casually as he possibly could.

Clemont replied, "Hm, now that you mention it, no, I haven't. I do believe Bonnie paid her a visit a while back, though. Why do you ask?"

"Ah, okay, thanks, I was just curious."

"Uh, Ash?"

"Yeah?"

"Why don't you just call Serena yourself?" Clemont asked.

Ash didn't know what to say. "Um...uh, I don't know if she still has my number," he said, which was actually true; given that he and Serena hadn't spoken in years, he really thought it was quite possible that she may have deleted his number.

Clemont laughed. "Are you kidding me? She probably has it tattooed on her...oh wait, scratch that. Bonnie told me she actually has a boyfriend now," Clemont said.

"Wait, what?" Ash asked, a little too aggressively. "Since when?"

"I'm not positive, but Bonnie visited her in March so I'd guess at least a few months or so," Clemont said. "Sounds to me like someone's a little jealous," he remarked, chuckling a little.

Ash's face grew a light shade of pink. "Are you crazy? I'm not jealous," he said. "Why would I be jealous?"

"I don't know, the same reason you're asking about her in the first place?"

"Okay, Clemont, very funny. My flight is boarding now, so I gotta go. It was great catching up with you," Ash said.

"You too, Ash. Stay safe on your trip, alright? And if you see any cool Alolan technology there, be sure to tell me about it," Clemont said.

"Of course, Clemont. There's no one else I'd talk to that stuff about," Ash replied. "Good luck on building your jet, you better give me a free ride when it's finished."

"You'll be the first to receive a complimentary, full-service trip to wherever you desire," Clemont said.

"Sweet! Alright, see ya later," Ash said, hanging up. He grabbed his backpack and picked up Pikachu, who had been busy eating ketchup straight from the packets. "C'mon, buddy, let's go!"

"It's Ash, mom. There, I said it," Serena said. "Are you happy to embarrass me like this?"

Grace was slightly taken aback by this. "Well, I didn't expect you to put it so bluntly. And no, dear, I am not trying to embarrass you. You know that. I just want to talk. What about Ash? I thought you haven't spoken in years."

"We haven't. That's exactly it...I want to talk to him so badly, I want to hear his voice, see his face, touch his skin…" Serena's voice trailed off as she fought back tears.

"Whoa, okay, slow down there. What about Calem?" Grace asked, thoroughly confused.

"What about him?"

"Well, he's your boyfriend, and I don't imagine he'd like what you're saying right now, honey. It seems clear to me that your affections aren't exclusively with him," Grace said.

Serena looked down at the floor. "I know...I feel so guilty for thinking about Ash but I just can't help it...but see? I told you you wouldn't be able to help me with this."

"Now hang on a second, I might not be able to magically summon this boy here with the snap of my fingers...but I am a mom, so I can give you some guidance, dear," Grace said.

Serena looked up. "And that is…?"

"You should end things with Calem. It's not fair to him for you to be like this. Imagine how he'll feel if he somehow finds out a couple more months down the road. It would crush him, sweetie. You're an amazing, beautiful girl, and I always knew you'd break boys' hearts left and right. I think you need to do this now, before you hurt Calem even more," Grace said. "And then, when the dust settles and you've gathered your thoughts a bit more, you should give Ash a call whenever you're ready," she added.

Serena looked out the window, unsure of what to make of her mother's advice. Maybe she's right, she thought. "I guess...you know, Calem is a nice guy, but I don't think I can actually see myself...loving him. But Ash...I mean it's been so long...what if he...gosh I just can't think right now," Serena said, frustrated.

Grace stood up to leave. "Well, I'm gonna leave you alone for a bit. Think about it hard, honey. Also, dinner will be at six," she said, walking out and closing the door behind her.

Serena looked down at her phone. After about a minute of hesitation, she picked it up and called Calem.

"Hey, Serena!" Calem cheerfully answered.

"Hey, Calem…" Serena said, her voice full of dread. She thought, Why is this so hard?

"What's up?"

"Um, I'm not quite sure how to say this, but we need to talk, Calem."

"Oh. Um, well okay, sure. Where should we meet? Should I bring some lunch? My mom just bought some of those cookies you like so much."

Serena smiled sadly. "No thanks, I'm not really too hungry. How about we just meet at the park by the Pokemon Center?"

"Sounds good, I'll be there in five minutes."

"Okay, see you there."

Serena hung up the phone.