A Night To Remember
Friday had arrived, and Ash Ketchum woke up feeling a mixture of excitement and nerves. It was finally happening. His first official date with May. After practice, he'd be taking her to the Pallet Town Fall Festival, one of the most celebrated events of the year. The festival was filled with games, food stalls, rides, and a sense of community that brought everyone together.
Ash sat on the edge of his bed, rubbing his hands together as he mentally rehearsed the evening. He'd planned every detail, wanting to make sure May had a night to remember.
His mom peeked into his room with a cheerful smile. "Good morning, Ash! Big day today, huh?"
Ash grinned nervously. "Yeah, it's a big day. Practice first, and then… well, you know."
Delia chuckled, stepping in to ruffle his hair. "Don't worry too much. Just be yourself, and she'll have a great time. Do you need me to pick up anything for you? Snacks? Flowers?"
Flowers. Why hadn't he thought of that? Ash jumped up, already scrambling for his wallet. "Flowers would be perfect, Mom! Can you grab some while I'm at practice? Nothing too fancy, just something nice."
"Consider it done," Delia's face lit up. "Oh, Ash, this is so wonderful! She seems like such a sweet girl. Where are you taking her?"
"I was thinking about dinner at that Italian place downtown, then maybe the fall festival. I want to make it special."
Delia nodded approvingly. "That sounds perfect. Just be yourself, sweetheart, and everything will go great. Have you thought about what you'll wear?"
Ash paused, realizing he hadn't even considered that. "Uh… I was just going to wear my usual stuff."
Delia gave him a look. "No, no, no. For your first date, you need to look your best. After practice, we'll make sure you have something nice to wear."
"Thanks, Mom," Ash said, feeling both grateful and slightly overwhelmed.
As he wolfed down breakfast, Delia watched him fondly. "You know, Ash, I've seen you work so hard on the baseball field, but this is something different. You're growing up, and I'm so proud of you."
"Thanks, Mom. I just… I really like her," Ash admitted, his cheeks turning pink.
Delia reached out, patting his hand. "I can tell. Now go on, or you'll be late for school."
The school buzzed with its usual Friday energy, students eager for the weekend. Ash navigated the crowded hallways, making his way to his locker. He spotted Brock, Gary, Paul, and Drew gathered near their usual spot by the cafeteria doors.
"Hey, Ash!" Brock called out, waving him over.
Ash joined them, leaning against the wall. "Hey, guys. Big plans for the weekend?"
Gary smirked. "I was going to ask you the same thing. Big date tonight, huh?"
Ash groaned. "Yup, it's gonna happen tonight. I'm going to see if she wants to make it official. No pressure or anything."
Drew crossed his arms. "So, what's the plan? Dinner and a movie? Or are you going to wow her with your deep romantic charm?
"Actually," Ash said, standing a little taller, "I'm taking her to that Italian restaurant downtown, then the fall festival. Figured it'd be more memorable than just a movie."
Brock nodded in approval. "Good call. May strikes me as someone who'd appreciate the effort. Just don't overthink it."
"I'm trying not to," Ash admitted. "It's just… I want it to go well, you know? I don't want to mess this up."
Gary clapped him on the back. "You've got this, man. You're Ash Ketchum. You don't quit, whether it's on the field or off."
Paul chimed in with a rare smile. "And if you do mess up, just laugh it off. Girls like confidence, even when things don't go perfectly."
Meanwhile in the Cafeteria
The warm aroma of freshly brewed coffee and the sound of chattering students filled the small cafe near the school. May and Dawn had snagged their favorite booth by the window, their trays of breakfast sitting untouched as they leaned forward, their voices low but filled with excitement.
"So," Dawn began, stirring sugar into her coffee with a knowing grin. "You and Ash, huh? Big date tonight?"
May blushed, her fingers fiddling with the edge of her napkin. "Yeah… he asked me on Wednesday after practice. It was so sweet, Dawn. He seemed so nervous."
Dawn chuckled, taking a sip of her coffee. "I can totally see that. Ash is such a dork sometimes, but it's part of his charm. He's probably overthinking everything about tonight."
May giggled, finally picking up her spoon to take a bite of her yogurt. "That's what I like about him, though. He's so genuine. He doesn't try to be someone he's not."
Dawn nodded in agreement. "True. But, spill the details, what are you guys doing tonight? Dinner? Movie? Something totally romantic?"
"He said dinner at that Italian place downtown," May replied, a shy smile spreading across her face. "Then maybe the fall festival if we have time. Honestly, I'm just excited to spend time with him outside of school and baseball."
Dawn gave an approving nod, setting her cup down. "That sounds perfect. Classic, but it gives you plenty of time to talk and just... enjoy each other's company." She paused, then leaned in closer. "But more importantly, what are you going to wear?"
May laughed, rolling her eyes. "Of course you'd ask that. I was thinking of wearing my red sweater with my denim skirt. Casual, but still nice, you know?"
"That's perfect," Dawn said immediately. "You'll look amazing. But, May… are you nervous?"
May hesitated for a moment, her smile faltering slightly. "A little," she admitted. "I mean, Ash is such a great guy. What if I mess up? What if I say something awkward, or he realizes I'm not as interesting as he thought?"
Dawn reached across the table, placing a reassuring hand on May's. "Are you kidding me? You're May Maple. You're smart, funny, and gorgeous. If anything, Ash is probably the one worrying about messing up. Trust me, he's completely into you."
May's cheeks flushed a deeper shade of pink. "You think so?"
"I know so," Dawn replied confidently. "Have you seen the way he looks at you? He's head over heels, May.
As their conversation continued, Dawn suddenly leaned forward, resting her chin on her hands. "So, do you like him?"
May froze mid-note, her cheeks flushing pink again. "What do you mean?"
Dawn rolled her eyes playfully. "You know exactly what I mean. Do you like Ash? Like really like him?"
May hesitated, her thoughts swirling. She thought about Ash's goofy smile, the way he always cheered her up during rough days, and how his determination on the baseball field was so inspiring. "I… I think I do," she admitted softly.
Dawn's grin widened. "I knew it! I mean, come on, May. You two are perfect together. He's funny, kind, and he clearly adores you. This date is just the start, I can feel it."
May smiled, her heart fluttering at the thought. "I hope so. He's such a great guy. I just don't want to mess it up."
"You won't," Dawn assured her. "Just be yourself, and everything will work out."
May smiled, a sense of calm settling over her. "Thanks, Dawn. I needed that."
Dawn grinned. "What are best friends for? Just promise me one thing."
"What's that?"
"Details," Dawn said with a wink. "I want all the details tomorrow. Every little thing."
May laughed, shaking her head. "Of course. I'll tell you everything."
The bell signaling the start of school rang in the distance, pulling them out of their conversation. May grabbed her bag and stood, feeling a mix of excitement and nerves fluttering in her stomach.
"Wish me luck?" she asked, glancing back at Dawn as they headed for the door.
"You don't need it," Dawn said confidently. "But good luck anyway. You're going to have the best time."
As they walked toward the school, May couldn't help but feel a spark of anticipation. Tonight wasn't just a date; it was a chance to see where things could go with Ash.
The late afternoon sun bathed the practice field in a golden glow as Ash and his teammates ran through their drills. Among them, May and Dawn sat side by side, chatting and occasionally shouting words of encouragement to the players.
"Nice hit, Ash!" May called out, clapping her hands as Ash sent the ball sailing into the outfield.
Dawn nudged her. "You've got it bad, don't you?" she teased, smirking.
May's cheeks flushed, but she laughed it off. "I don't know what you're talking about."
Before Dawn could press further, a familiar voice behind them interrupted.
"May?"
May turned to see a girl with honey-blonde hair and a warm smile standing a few feet away. She recognized her from earlier that week, Serena, Ash's old friend who had just transferred to their school.
"Serena, hi!" May said, standing to greet her. "I didn't know you'd be at practice today."
Serena gestured toward the field. "I wanted to see how everyone was doing. It's been so long since I've watched Ash play. Mind if I sit with you two?"
"Not at all," Dawn replied, motioning to the spot next to her and May.
Serena sat down, her gaze lingering on Ash as he prepared to pitch. For a moment, a thoughtful silence hung between them, broken only by Dawn excusing herself to grab something from the concession stand. Once they were alone, Serena turned to May with a soft, almost hesitant smile.
"You and Ash seem really close," Serena began, her tone casual but laced with something deeper.
May shrugged, a small smile playing on her lips. "I guess so. He's been really sweet lately. He even asked me out on a date for tonight."
Serena's expression shifted slightly, still warm, but now tinged with a bittersweet edge. "That's wonderful. I'm happy for you two."
May tilted her head, sensing there was more Serena wanted to say. "Have you known Ash for a long time?"
Serena nodded, her eyes fixed on the field. "Since we were little kids. We used to play baseball together all the time. Ash, Gary, Brock, Paul, and actually, we'd spend hours outside, making up games and having fun. Those were some of the best memories of my life."
May smiled, picturing a younger version of Ash with Serena and their friends. "It sounds like you all were really close."
Serena hesitated, her hands fidgeting in her lap. "We were. And, to be honest, there was a time when I thought… when I thought I had feelings for Ash."
May blinked in surprise, unsure how to respond. Serena continued before she could say anything.
"It wasn't serious, just a crush," Serena said quickly, her cheeks tinged pink. "But it's funny. The more time we spent together, the more he talked about you."
"Me?" May asked, her voice rising slightly in surprise.
Serena nodded. "I will admit before I came here, I was going to tell him how I felt when I was younger and hoped that he shared the same feelings but we met together with Gary on the same week I came back and he couldn't stop mentioning about this amazing girl he'd met. He talked about your smile, your laugh, how you cheered him on during games. It didn't take long for me to realize that Ash… well, he's crazy about you."
May felt her heart skip a beat, warmth spreading through her chest. She looked down, her fingers twisting nervously in her lap. "I didn't know he talked about me that much."
"He does," Serena said, smiling softly. "And that's when I decided to let go of any feelings I had for him. Ash is my friend, and more than that, he deserves to be happy. And I think you make him really happy, May."
May was quiet for a moment, processing Serena's words. Finally, she looked up, her expression thoughtful. "Serena, I really appreciate you telling me this. I can tell how much Ash means to you as a friend, and I promise I'll do my best to make him happy, too."
Serena's smile widened, her earlier hesitation melting away. "I know you will. You're a great person, May. And honestly, I think Ash is really lucky to have you in his life."
The two girls exchanged a warm look, a newfound understanding forming between them. They turned their attention back to the field, where Ash was wrapping up his pitching drills. His focus and determination were evident in every throw, and May couldn't help but feel a swell of pride watching him.
As practice came to an end, the players began gathering their gear and chatting among themselves. Ash spotted May and Serena in the bleachers and jogged over, his face lighting up when he saw them.
"Hey, you stayed the whole time," Ash said, slightly out of breath but grinning nonetheless.
"Of course," May replied, smiling back. "You looked great out there."
"Thanks," Ash said, scratching the back of his neck. He glanced at Serena, his grin softening. "Hey, Serena. It's good to see you here."
Serena stood, her expression warm. "You were awesome, Ash. Just like old times."
Ash chuckled. "Thanks. It means a lot coming from you."
As the three of them chatted, May couldn't help but notice the easy camaraderie between Ash and Serena. It was clear they shared a deep bond, one built over years of friendship. But as she listened to their conversation, May felt no trace of jealousy, only gratitude.
Ash felt a sense of happiness appear on his face. "Ill pick you up tonight at 7, okay May.
"That sounds perfect!" May said. Her excitement was unmistakable.
"Great," Ash replied. "I'll see you then, Bye Serena!
See you then. May responded
Bye. Serena responded to Ash. Good luck tonight May, youre gonna do great!
Thanks Serena, and thanks for the reassurance Ill let you know how it goes!
That night
Ash stood in front of his mirror, giving himself a final once-over. He smoothed down his casual black shirt and adjusted the collar of his black trucker jacket. The dark blue jeans fit snugly, and his black biker boots were polished just enough to look sharp without being flashy. For once, his trademark hat was nowhere in sight, replaced by his naturally messy hair being slicked back in a bit of a more clean and edgy look.
"You've got this," he told his reflection, though his stomach churned with nervous energy. Tonight wasn't just another outing with a friend, this was a date with May. The night that he was going to confess his feelings. He took a deep breath, grabbed his keys, and headed downstairs.
Delia was sitting on the couch watch her show when she paused it to look at her son.
My little boy is all grown up now. She said with tears forming in her eyes. Good luck tonight Ash, go get her!
I will mom, I promise! And with a final goodbye he was out the door.
When he arrived at May's house, the nerves intensified. He knocked on the door, and moments later, May opened it, looking radiant, deciding to go for a more cute but casual look wearing a flowy lavender top and fitted white jeans, her hair cascading in soft waves over her shoulders. Her smile lit up her entire face, and Ash felt his heart skip a beat.
"You look great," Ash managed to say, his voice steady despite the butterflies in his chest.
May blushed lightly. "Thanks, Ash. You look really nice too."
Suddenly he pulled a bouquet of roses from behind his back.
¨Oh Ash, these are beautiful, I love them thank you!¨ she responded with happiness in her tone.
¨Of course, the pleasure is mine¨ He responded trying to be as polite as ever.
She gestured toward the driveway. "Shall we?"
Ash opened the passenger door of his car for her, earning an appreciative smile, as he walked around the car he peeked through the backseat window to notice May reaching over to unlock the driver side door for him. He had to admit he let out a little cheer before he climbed into the driver's seat, she had officially passed his test with flying colors.
The drive to the restaurant was filled with light conversation, their laughter breaking through any lingering awkwardness. By the time they pulled into the parking lot of a cozy Italian restaurant, they were both relaxed and excited for the evening ahead.
Inside, the restaurant was warm and inviting, with soft lighting and the aroma of fresh pasta and garlic filling the air. The hostess seated them at a small table by the window, giving them a perfect view of the twinkling city lights.
"This place is amazing," May said, glancing around as she picked up the menu. "How'd you find it?"
Ash grinned. "My mom actually recommended it. She said it was the perfect place for a first—" He stopped himself, his cheeks heating up. "Uh, I mean, a nice dinner."
May giggled, clearly catching his slip but choosing not to comment on it. "Well, she certainly has great taste."
They ordered their meals, Ash went for the spaghetti and meatballs while May chose a stuffed crust pizza. As they waited for their food, the conversation flowed easily. They talked about school, their friends, and, of course, baseball.
"You must have been incredible as a kid," May said, her eyes sparkling with genuine admiration. "Serena told me about how you, Gary, and Brock used to play on the street all the time."
Ash chuckled, leaning back in his chair. "Yeah, we were pretty scrappy back then. We didn't even have proper bases, just random objects we'd find lying around. But those games are some of my favorite memories."
May rested her chin on her hand, her gaze never leaving his. "It's amazing how passionate you are about baseball. You make it look so effortless. I also want to say thank you for being my first official friend when I moved here. I will admit that I was really nervous, I didn't think that I was going to be accepted so easily, you know being the new girl and all."
Her words made Ash's heart swell with pride, and he couldn't help but smile. "Thanks, May. That really means a lot. And you don't have to thank me whatsoever. Im always going to be here to help."
Their meals arrived shortly after, and they ate while continuing to talk and laugh. Ash couldn't remember the last time he'd felt so at ease with someone. By the time they finished dessert, a shared slice of tiramisu.
After dinner, they headed to the fall festival, the atmosphere buzzing with energy. String lights hung overhead, illuminating the rows of booths, rides, and food stands. The air was filled with the scent of caramel apples and popcorn, and the sound of laughter and music surrounded them.
"This is incredible!" May exclaimed, her excitement contagious as she looked around. "Where should we start?"
Ash pointed toward a ring toss game. "How about there? Let's see if I can win you a prize."
They made their way to the booth, where Ash paid for a few rings. He focused on the bottles lined up in front of him, carefully aiming before tossing the first ring. It missed by a hair, and May stifled a laugh.
"Don't worry, you've got this," she teased, nudging him playfully.
Ash smirked, determined now. His next toss landed perfectly, and the booth attendant handed him a small plush Eevee. Ash turned to May, holding it out to her.
"For you," he said, his grin widening when she accepted it with a shy smile.
"Thanks, Ash. It's adorable," she said, clutching the plushie to her chest.
They spent the next hour exploring the festival, playing games, and sampling treats. Ash impressed May with his aim at the dart-throwing booth, and May managed to drag Ash onto the Ferris wheel despite his initial hesitation.
As they reached the top of the Ferris wheel, the view of the festival below was breathtaking. The lights twinkled like stars, and the distant sounds of laughter and music felt almost magical. May looked out over the scene, her expression serene.
"This is perfect," she said softly, turning to Ash. "Thank you for tonight. I haven't had this much fun in ages." As she said that last statement she laid her head on his shoulder, taking in the moment.
Ash felt a surge of courage and reached for her hand, which rested on the edge of the seat. "I'm really glad you came, May. Tonight's been… amazing."
She looked down at their hands, a soft blush coloring her cheeks, but she didn't pull away. Instead, she tightened her grip, her smile growing.
When the ride ended, they continued walking through the festival, stopping at a photo booth on May's insistence. The resulting strip of pictures captured their laughter and goofy expressions, which May tucked into her bag as a keepsake.
As the night wound down, they found themselves at the festival's main stage, where a small live band was performing. The music was soft and melodic, the song It Had To Be You by Frank Sinatra began to play, a few couples were swaying together under the string lights.
"Dance with me?" May asked suddenly, surprising Ash.
"I… uh…" He hesitated, but the hopeful look in her eyes made it impossible to say no. "Okay."
He led her to the makeshift dance floor, his nerves fading as they began to sway to the music. May rested her hands on his shoulders, and Ash placed his hands lightly on her waist. Their movements were a little awkward at first, but soon they fell into an easy rhythm.
"This is nice," May said, her voice barely audible over the music.
"Yeah," Ash agreed, his gaze meeting hers. "It really is."
For a moment, it felt like the rest of the world had faded away. It was just the two of them, surrounded by the warm glow of the festival lights and the gentle hum of music.
¨ Listen May, I need to tell you something.¨ Ash hesitated
¨ Of course Ash, what is it?¨ she responded with a hint of curiosity in her tone.
Ash knew it was now or never, he began: ¨Well, if I must be completely honest, I have feelings for you May. I know this might sound crazy, but I feel a special connection when were together. Not only are you absolutely breathtaking, but the way that you always have my back during every game, even when I injured my shoulder you were the first one who checked up on me constantly and especially when meeting your family and how welcoming they were, it was an incredible feeling. I know I'm rambling on but I'm just gonna ask, May Maple, will you be my girlfriend?¨
For a second it felt like time had stopped. To say that May was not expecting this out of Ash would be an understatement.
¨Yes, Ash. Of course!¨ She responded out loud. ¨I would be a fool if I said no! I will absolutely be your girlfriend!¨
Both teens embraced in a long everlasting hug with May being swung around in a circle where they both sealed the deal of their new relationship with a kiss underneath the moonlight.
When the song ended, they reluctantly pulled apart, though their hands lingered for a moment longer. As they walked back to the car, both of them were quieter, lost in their thoughts about the night.
Ash opened the car door for May, and as she climbed in, she looked up at him with a smile that made his heart race.
As they approached the Maple residence and her front door, May spoke.
"Thank you, Ash. Tonight was perfect. And for the record I would have said yes 1,000 times!"
He smiled back, his confidence growing. "Anytime, May. Thank you for an incredible evening, I can't wait to share the news with the others! Before they parted ways they kissed one final time signaling the end of an unforgettable night.
A/N: Annnd we officially have a couple on our hands. It only took 4,000 words in this chapter but we finally made it! I was so excited to write this chapter out. I want to thank everyone who has left a review or a follow. I appreciate it, now I will be taking the time to focus more on how Ashs baseball career shall play out. Will he make it to the big leagues? Find out in the next chapter!