It was late in the afternoon when Ash and his friends checked into the Pokemon Center. They were going out to dinner soon, courtesy of Brock, but none of them were excited about it. Max was sitting at a table, fidgeting with a die, while Brock was sitting on the couch, arms folded with a somber expression. He didn't even respond when Nurse Joy walked by him. Ash was sitting beside him, his head resting in his hand, with Pikachu curled up beside him. As for May, she was out somewhere. She had asked for some time alone earlier after a particularly hard contest she ended up losing.

She did well in the contest, easily pulling through the appeals round and blasting through the first battle round with flying colors. However, once she got to the final round, she found herself dead even with her opponent. The two of them constantly outmatched the other, it seemed, constantly trying to get a step ahead. In the end, it came down to the time running out. Because her opponent had just a few more points than her, he was declared the victor. The two of them congratulated each other before he received his ribbon, but when she went backstage, she dropped her smile. Despite her friends' comforting encouragement, she didn't perk up like she usually would after a loss.

The center remained quiet for quite some time until Nurse Joy emerged. "Is Ms. Maple here?" she asked, carrying out a tray of Pokeballs.

"No," Max replied, looking up from his cube.

"Well, could one of you please tell her that her Pokemon are all rested up?"

"Sure," he shrugged.

"Okay," she said, smiling as she set the tray next to Max. "She sure is lucky to have friends like you guys." With that, she went back behind her desk.

Brock looked up at the clock. "It's almost dinnertime," he said. "I'll get our reservation tickets so we can go."

"Okay," Max shrugged, standing up. "If you need me, I'll be outside. I think I need some fresh air." With that, the two boys went in opposite directions, leaving Ash alone with Pikachu.

"I wonder why May's upset," Ash mumbled out loud.

"Pika?" Pikachu said.

He turned to his Pokemon. "I mean, she's lost before, and while she's always bummed about it, she also cheers up after a little bit. What's going on with her?"

"Pikachu," Pikachu shrugged.

Ash sighed and stood up. "I'm gonna go look for her," he said. "You coming?" Pikachu shook his head and curled up again. "All right," he smirked, petting Pikachu's head. "I'll be back soon." With that, he walked out the front door.

They were in a small town that enjoyed ordinary natural wonders, like a small creek flowing through or naturally growing trees. It practically blended in with the surrounding environment, making it difficult to know where the town ended and the route began. This wasn't a problem for Ash, however, as he walked outside the town border and looked around for his friend. "She wouldn't have gone far," he thought to himself out loud. "Maybe she's still in town." Just as he started to turn back the way he came, however, he heard a soft sound. It was a sad sound, as though someone were crying softly.

His eyes widened on hearing it, and he walked quickly in its direction. Before he knew it, he saw a familiar friend sitting hunched over on a log. It was May. Her face was in her hands, her shoulders shaking slightly as she quietly cried.

Ash looked at her with sadness, but also curiosity, and he slowly made his way towards her, careful not to alert her. When he was close, he sat down next to her. "May?"

She gasped and looked up, then relaxed when she saw who it was. "Ash?" she said, blinking. Her eyes were slightly moist. "What are you doing here?"

"I could ask you the same thing," he said, scooting closer to her. "What's wrong?"

At that, May turned away and started sniffling again. "It's nothing," she said.

Unconvinced, Ash scooted closer. Now directly beside her, he put his arm around her shoulders, giving her a gentle squeeze. "It's all right. We're here for you."

"It's nothing," she said again, warming up slightly from his touch. "I'll be fine."

"You don't seem fine right now," he replied, firmly yet gently. "Come on, May. What's the matter? You know you can tell me anything."

May hesitated for a moment. Then she wiped her eyes and turned to him. "I lost today," she said. "My Pokemon and I gave everything we had, and it wasn't enough."

"You guys did really well," Ash replied, smiling softly. "You shouldn't feel ashamed just because you lost. When you give everything you have in battle, it makes you stronger."

"But we still lost," May replied, a new stream of tears flowing down her face. She started sobbing softly. Ash opened his mouth to say something, but before he could, May leaned into his shoulder. He felt her tears drip onto his shirt. Ash tried to say what he was going to say, but his words caught in his throat. In the end, he gave up and just put his other arm around her, embracing her as she cried into his shoulder. It was about thirty seconds before she calmed down. He pulled his arms back, and she sat up, wiping her eyes.

"Sorry," she said.

"For what?" he blinked, confused.

"For being such a crybaby," she replied. "I shouldn't cry like that when I lose. You're right; I have nothing to be ashamed of." She gave him a smile.

It was a fake smile, one which she had given many times. It was only now that Ash realized this, as her eyes still betrayed her sadness. He looked intently at her, wondering. As though reading his thoughts, she jerked her gaze away from him, looking downwards. Seeing this, he gently put his hand on her shoulder. She flinched slightly at his touch.

"You're not a crybaby," he said. "Why would you think of yourself like that?"

"Because I cry every time I lose," she said, dropping the fake smile. "I'm better than that; I don't have to cry."

"No, you don't," Ash agreed, "but it's not necessarily a bad thing."

"Not a bad thing?" May repeated, glaring up at him incredulously. His hand slipped off her shoulder. "Ash, I'm sixteen years old! I'm not a child anymore! I shouldn't be crying because I lost in some stupid contest!" He didn't waver from her outburst, prompting her to look away again. "Sorry. I didn't mean to snap."

He looked at her again with the same gaze she had looked away from before. This time, he could see her eyes, even though she was looking down. Something about them seemed sad, as though they could never be good enough. He thought for a moment about what she had said. After some careful thinking, he spoke again:

"Who told you that you were a crybaby?"

She blinked, startled, and looked back up at him. "What?"

"Who told you that you were a crybaby?" he asked again, firmly yet gently.

"N-No one," she replied, confused. "What makes you think someone told me that?"

"Because you wouldn't think of yourself like that if no one had called you that," he replied.

She blinked, then looked away, tensing up slightly. "No. Nobody's ever called me names. Not even the playground bullies when I was a kid."

"Nobody?"

"No one."

"Nobody at all?"

"No."

"Not a single person has ever called you that before?"

"What's the point of this?!" May snapped, glaring at him again. Ash remained calm, knowing he was getting somewhere.

"I want to help you," he said. "I want you to understand that you are not a crybaby, no matter how many times you cry after losing a contest." May blinked, then turned away again without a word. He put his hand on her shoulder again, still gentle. She pulled away and hugged herself tightly, closing herself off from him. In response, he stood up and knelt down in front of her, locking his eyes with hers. She tightened her arms around herself, but no matter how much she wanted to, she couldn't tear her eyes away from him. "May, I know you, and you are not a crybaby. When you cry, I don't think you're being a baby. I think you're sad, and it makes me sad, too." He put his arms on her shoulders, looking deep into her eyes. "I want you to be happy."

Tears needled May's eyes as her arms started to loosen. Her throat constricted, but she fought back against her emotions.

"It's okay to cry," he said. "Why do you think it's not okay?"

She tensed up again, her lower lip trembling. Please, stop it Ash.

"Have people told you that it's not okay to cry? Did one of your parents tell you?"

Please stop. Don't say it.

"Your mother?"

No! Please, don't say it!

"Your father?"

With those two words, the dam burst. May collapsed into his arms, sobbing as tears flowed down her face. Ash was initially taken aback by her sudden outburst of emotion, but he quickly put his arms around her, embracing her and gently pressing her head into his shoulder. She let all inhibitions go as she sobbed loudly, muffled only by the soft fabric of his jacket. She clutched his jacket tightly with her arms, while he held held her tightly yet gently. Through her sobs, Ash could make out two words, repeated over and over again: "I'm sorry."

"Shh," he whispered softly, stroking her hair. She seemed so fragile and delicate, like a precious vase in his hands. As he held her, he thought of her father and how the two had interacted whenever they were at her home. He never thought much of it at the time, but as he looked back, he remembered how they hadn't really spoken that much. He'd always talked about Max, showing pride in his son's intellect, and only talking to May if he needed something from her. It was then that Ash realized the truth:

She was distant from her father.

No sooner had he realized this than she stopped sobbing, pulling out of his embrace. She wiped her reddened eyes and sniffed heavily. "No," she said after a moment. "No one's ever told me it wasn't okay to cry. But that's not why I've always thought I was a crybaby for crying after losing a contest."

"Then why do you think that?"

She sniffed again. "My father groomed me to be a gym leader when I came of age," she explained. "So when I chose to be a coordinator, it threw off his idea of what I should be." She wiped her eyes again. "It's been difficult between us ever since."

Ash nodded in understanding. "I'm sorry," he said softly.

"Don't be," she replied. "It's not your fault. I've just wanted so badly to know that no matter what he thinks of me, I've made the choice and chosen the right path. And every time I lose, it just feels like what he thinks is right."

"You can't think like that, May," Ash said firmly, putting his hands on her shoulders. "Whatever dreams your father has for you, they will ultimately come second to whatever dream you have for yourself, especially as you grow up."

"Easy for you to say!" she snapped back. "It's not like you have a dad who expects you to be something you're not! You don't have to feel that kind of pressure every time you put yourself out there on the battlefield!"

At this, Ash loosened his grip on her shoulders and dropped his arms, looking down at the ground so that his hat concealed his eyes. His lips curved into a somber frown. "No," he agreed in resignation. "You're right. I don't."

May blinked, surprised at his sudden change in mood. That must've hurt him more than I thought she realized. "Ash, I'm sorry, I didn't mean -"

"It's okay," he said, looking up at her. "You didn't know, and neither do I." He put his hand on her arm, sending shivers down her spine. "But May, you need to stop worrying about what you dad thinks. I'm not gonna pretend to know what it's like between you two, but if you're always trying to prove that you're right and he's wrong, then you'll never be truly happy. You'll only feel true happiness when you accept that this path you've chosen is the right path, no matter what anyone says or thinks. This is your life, your journey, not theirs."

She gazed into his eyes, her own eyes glimmering as tears bristled in them again. A smile slowly formed on her face, though this time it was a real smile. "How do you do that?" she asked.

"Huh?"

"How do you always say exactly what I need to hear?"

He blinked, then smiled softly. "Well, what are best friends for?"

She responded by putting her arms around him and embracing him tightly. Tears streamed down her face, no longer from shame and sadness, but rather from happiness. They once again flowed onto Ash's shirt as he embraced her. He slowly rubbed her back, stroking her hair while they stood underneath the sunset.

"Thank you, Ash," she whispered into his ear.

"Always, May," he whispered back. They parted after several seconds, gazing at each other a moment more before turning back towards the setting sun. "Think we should head back?" he asked.

"Yeah," May nodded. "I'm a little hungry, and I think it's about dinner time."

"Same," Ash agreed. With that, the two of them started walking back. As they walked, Ash felt a hand lace into his own. He looked down and saw a familiar gloved hand. He looked back up and saw his friend smiling at him.

"You don't mind, do you?" she asked innocently.

"N-No," he replied, a light blush creeping onto his face. May giggled at this as they walked back into town. At this, Ash smiled. He'd missed her cute giggle.

It was nice to see her happy again.

This story started as an attempt to deconstruct a cliche premise: May is sad about something, she cries about it, and then Ash cheers her up. I see it in so many fics, and while it's not necessarily a bad thing, it gets used a lot to the point where it can become a little predictable. However, I think this story evolved slightly beyond my original intentions.

Whether that's a good thing or a bad thing, I'll leave up to you. Feel free to rate and review, but please be constructive.

On another note: 50th story! Yay!