Ash was really dense when it came to anything outside of his expertise, though one might argue he was still dense concerning Pokemon and hardly knew a thing he was doing... but that's besides the point.

While Ash was often incredibly lucky and could wing it through any situation, this matter was a little different. Something completely out of his comfort zone. Something involving a feeling which he harbored for awhile, only having acknowledged it more recently, and has now led him into a predicament that was causing him to internally freak out.

"Brock, what are you supposed to do on a date?" Ash asked.

Brock was so taken aback by the question, he had to do a double take. "Say that again?"

"A date! Misty and I are going on a date and I have no idea what I'm supposed to do!"

"Just be romantic?"

"I have no idea how to BE romantic!"

Brock chuckled. "Can't deny that."

That wasn't helping Ash's confidence, but he was the one that admitted it, not Brock.

"Hmmm..." Brock thought for a moment. "Your safest bet is with the classics. Give her some chocolate or some flowers she likes."

"I don't know what kind of flower she likes."

Sighing, Brock decided to take another approach. "Alright. Take her somewhere nice. Where do you plan to go?"

Ash shrugged.

"You mean you don't even have a plan?"

"Not really."

This was going to be tough. Romance was clearly outside of Ash's realm of expertise and was probably a completely foreign subject, even now, after all these years.

"You know Misty likes you, right?"

"Yeah. She told me."

"And I'm safe to assume you like her back?"

"Of course I do!"

"Well, then the best option is just be yourself."

"Myself?"

"Yeah." Brock nodded. "She fell in love with you, so just do the things you would normally do, except with no one else around. Just the two of you, being yourselves."

"You mean I can't bring Pikachu?" Ash's tone of voice sounded a bit strained.

Brock scratched under his chin in thought. "Well... having Pikachu along should be pretty safe, considering how well he gets along with Misty anyway."

Ash heaved a sigh of relief. His nerves would have been more shot if he didn't have his little buddy by his side. "Alright, just be myself. That's all it will take."

The doorbell rang, causing Ash to stiffen. "She's already here?!"

"That was fast."

"Oh shoot, where's my hat?" Ash frantically looked around, until he found it sitting on a sofa arm. "Pikachu! Let's go! Misty's here!"

"Pi-pi-pi!" the little electric mouse sped out of nowhere, jumping on Ash's shoulder.

"Alright. Let's make it count, Pikachu."

Taking a deep breath, Ash opened the door - only for said breath to be stolen by the sight that laid before him. Misty was wearing a sky blue blouse with matching skirt, and she wore her hair down - the bangs kept out of her face via headband.

"Pika..."

Even Pikachu was mesmerised.

"Hey Ash!" she smiled. "Sorry I'm a little late, one of my matches at the gym went a little overtime and so I couldn't close as early as I wanted to. Ash?"

She blinked, noticing how he kept staring at her, dumbfounded. "What?"

"Oh, nothing, you just look..." Ash didn't even have words to describe.

"Pi Pikachu!" Pikachu chimed.

"That's right, Pikachu. Pretty. You look very pretty, Misty."

"Ah...!" Misty's face flushed, and she had to turn her gaze to the side. "Well, uh... thanks, that's very sweet of you."

They were silent for the next two seconds, until Misty cleared her throat. "So, Mr. Pokemon Master, where will you be taking me tonight?"

Ash shrugged. "I don't know."

"You don't know?"

"Nope."

"Ugh..." Misty smacked her forehead. "Why is it that I expected more from you on our first date when I clearly knew better?"

"We could always go somewhere you like."

"Huh?"

"I know I'm not very good with all this 'love' stuff, but I'm pretty sure dates are supposed to be fun, and that you're supposed to enjoy it, so why don't we go where you want?"

"Ah... well... then..." Misty's brain felt scrambled. She was unprepared for this, but quickly gathered her bearings. "There's a lot of really neat sights here in Cerulean City that I've always wanted to show you. I don't think we can check them all tonight, but we could get started."

"Sounds good." Ash nodded. "You don't mind if Pikachu tags along, do ya?"

"Not at all!" And as she said that, Pikachu jumped into her arms - causing Misty to giggle as she rubbed her cheek against his electric pouch that gently sparked.

"Hey, Misty's my date, not yours." Ash stated in mock jealousy.

"Oh, Ash, don't worry - I'll give you some attention too." With that, Misty hooked arms with Ash, giving him a kiss on the cheek.

"Y-Yeah... so will I..."

Ash really wasn't sure how to respond, so he decided to follow Misty's lead and give her a kiss on the cheek too. She gasped in shock, turning red. "Ash!"

"Did I do something wrong?"

"Ah... n-no... but...!" Misty groaned, realizing she was just as much a hopeless mess as he was.

"Oh, right. I'm supposed to do it like this." Ash leaned in, bending a little to give her a kiss on the lips. It was short and subtle, almost barely felt it, but caused Misty's heart to race the second their lips met.

Pikachu's ears went up, eyes wide at his trainer's boldness.

"Ash... you...!"

Ash nearly panicked, wondering why Misty was getting so worked up. "Wh-What?"

Misty sighed, but then cracked a bit of a smile. "Idiot."

Wrapping her arms around his and leaning to his side, Misty led him to the first sight she wanted to show him on their date. Ash may be really dense when it came to love, but he always tried his best, and she had no doubt it was all with the best intentions. After all, as awkward as that kiss was, it felt incredibly genuine and she couldn't wait to return the favor when the night was done.

A/N: Day 1 of Pokeshipping Week 2023 "First Date". I had a lot of fun with this piece. I honestly think Ash would have no idea what to do on a date, and clearly be stumbling through it all. So I just rolled with that.