I apologize that I've been lazy for the last couple chapters, I've been trying to think up a better plot line. LaprasIzLife also recommended that I put the boys on some sort of sports team, so I'm gonna use that. This chapter will be focused a TON on Advanceshipping. Don't worry, Ikarishipping is still the main pairing, I'm just having writer's block when it comes to what I'm gonna do next for them. Anyway...

(Ash's POV)

Ash was the first to wake up the next morning, which was strange for him. When Barry (who's usually the early bird) woke up, he asked Ash in disbelief, "Everything alright?"

"Yeah," Ash said, distantly. "I'm just worried I'm gonna totally blow it on my date tonight. I'd never so much as held a girl's hand until yesterday! In fact, I didn't understand love until I was twelve!"

Barry was shocked that Ash, who was usually so laid back and happy, could be so stressed. "Um, I don't really know about this kind of thing," he said, awkwardly. "But you could ask Drew or Gary for advice. They're better with girls, so people say."

As if on cue, Drew snapped up. "Wazzat?" he muttered, sleepily.

"Ah, it's nothing, Drew," Barry said. "But you should look at your hair. You've got the worst bedhead ever this morning."

"What?" Drew said, suddenly wide awake. "My hair? Bedhead?" He zoomed out to the bathroom.

"Gary! Wake up!" Barry yelled, throwing a pillow at him.

"I was having a good dream..." he muttered. Ash snorted.

"What, about the girlfriend you're never gonna have?" he asked, laughing.

"Watch it, Ashy boy," Gary grumbled, sitting up. Ash glared at him.

"DO NOT CALL ME ASHY."

"Okay, boys," Barry interrupted, brightly. "We've got a full day ahead of us! At lunch, we need to meet Misty, May, and Iris to start plotting operation 'Get Dawn and Paul together, somehow', and we need to get Ash ready for his big date!"

"Oh yeah," came Drew's voice, sarcastically from the bathroom. "The romantic dinner at Denny's."

"Hey, I know the one way to her heart is breakfast food," Ash said, defensively. "We've been friends since second grade."

"It's ironic you're taking her to a breakfast place for dinner," Gary said, smirking.

"ANYWAYYYYYY..." Barry interjected before Ash could respond. "Have we got everything checked off for our morning ritual? Ash and Gary fighting. Check. Me spelling out the day for us. Check. Drew obsessing over his hair. Check. Gary putting obscene amounts of hair gel in his hair to keep it spiky. Check. 'Kay, we can go to breakfast now."

They headed down to the cafeteria, where the special was french toast.

"Aw, heck yeah!" Ash cheered, pumping his fist, and dashed to join May in line.

"How's it going, Ash?" she asked. They'd got a lot more comfortable around each other after he'd got the guts to ask her out.

Ash shrugged. "Pretty good. I'm excited for tonight."

"Me too," May said, gratefully. "The other girls keep teasing me about it, though."

"I know, right?" Ash agreed, as the cafeteria lady dished their french toast onto their trays. "Gary and Drew are giving me a hard time about it."

May shrugged. "Eh, they're just jealous they don't have anyone to go out with," she decided. They had both filled up their trays, by then.

"Well, I'll see you later," Ash said.

"See ya!" May said, smiling. And they both went to sit at their separate tables.

*WEIRD TIME TRANSITION TO LUNCHTIME*

Ash, Gary, Drew, Barry, Iris, May, and Misty were all gathered at a table.

"How are we gonna do this?"

"Well, we need him to confess his feelings, somehow."

"That's not gonna be easy. He's the most introverted person I've met.

"Or we could get Dawn to confess her feelings."

"If she has any."

"We haven't decided if she likes him or not, remember?"

They plotted it for a while, but agreed to discuss it later, as Ash and May were out of it.

"I'll see you tonight?" Ash asked May, hopefully, as they parted ways.

"Yup," she agreed.

*YET ANOTHER TIME TRANSITION TO LATER THAT NIGHT*

Ash walked up to May's dorm room, and knocked on the door. He heard some scuffling, and Dawn opened the door. "Hey Dawn," Ash greeted. "Is May here?" Dawn giggled, and he heard more giggling in the background.

"Yeah, I'll go get her," she said, smiling. Ash stood there, feeling awkward as he heard whispering and giggling again. May sprinted to the door. The brunette was wearing a long sleeved red blouse and a black skirt.

"I didn't want to look too formal," she apologized. "Since we're only going to Denny's."

"Nah, you look great," Ash said. And he really meant it. May blushed. "So, since I don't have my driver's license quite yet," Ash continued, as they exited the school building. "We're taking the bus."

"Ooh, romantic," May teased. Ash laughed.

"Yeah, just be glad we're not walking in the snow," he replied, chuckling.

"Where's Pikachu?" May asked. Ash always carried his Pikachu around with him, but this time, it was nowhere to be found.

"Oh, Barry, Gary and Drew are watching him," Ash explained.

"I hope that works out for them," May joked, and they both laughed. Ash was happy already. May was just so...easy to be around. They could be on a date, but still joking like twelve year old's, just like old times. They took the bus to a stop nearby Denny's, and entered it.

There was practically no one there, and the waitress at the front seemed relieved for some business. "Right this way," she said, and guided them to a table. They both sat down, and took a look at their menus.

Once the waitress swung by again, they ordered their meals. They began to chat about taking care of their Pokemon, and talked about how weird their friends were, and made fun of Gary happily. They ate their meals, and headed back to the school.

Ash walked May back up to her dorm. Before she entered, she turned to him. "Thanks, Ash, I had a ton of fun," She said, truthfully, and kissed him on the cheek quickly. She walked into her dorm, leaving Ash with his cheeks burning.

He headed back to his dorm, expecting an electrocuted Gary holding Pikachu, an excited Barry asking him how it went, and Drew making snooty comments about May kissing him.

He was greeted with just what he was expecting.

Whew! This one took a while to write, and I think it's the longest one I've done so far, but I'm happy with it. It was fun to write because Ash and May have such great chemistry. Thanks for your continued support!