Author: *cracks knuckles* Another chapter down, so many more to go.
Early the next morning, Ash and Max found themselves pacing in the living room, waiting for the ladies to join them so that they could head to the port. An amused Red sat on the couch, having discovered that watching their display of impatience was an easy way to pass the time.
"What is taking them so long?" Max exasperated.
"If we don't get going soon, we're going to miss the boat," Ash lamented before turning to Red. "Maybe we should wake mom up and say goodbye again."
"You do realize if we do that, she'll wait until we're headed out the door to lecture us about changing our underwear in front of everyone right?" Red responded with his arms crossed.
"Forget it," Ash said sheepishly.
"Anyways, I have an idea," Red began with a grin, before raising his voice in the direction of the stairs. "Sure guys, I think we should leave without them. There's no reason all of us should miss the boat."
Moments later, several crashes were heard, followed by muffled cursing and scrambling footsteps. May and Serena then both rushed down the stairs with their bags, their hair still wet and styled normally, but still frizzy.
"Don't you dare you jerks!" They exclaimed in unison. Opening their eyes after their outburst, they noticed only Ash, Max, and a Red-shaped cloud of dust in the room near four tickets.
"Hopefully by the time they get to the dock, they'll have calmed down," Red muttered to his Umbreon as they dashed away from the house, only to slip on a patch of ice that suddenly appeared in front of him. He landed hard on his rear end, before slamming his head against the ground, falling unconscious. A red-faced May then came up to him, grumbling something about a girl's hair being her life and how skipping breakfast should be a crime. Putting aside her anger for a moment, she quietly praised Glaceon for forming the ice, then grabbed him by the collar of his shirt and began to drag him towards the dock. Noticing Serena was giving them a glare, Ash and Max quickly fell in line behind May, quietly murmuring something about being falsely accused.
Most of the walk to the port was uneventful for the group. After a few minutes, Red awoke somewhat dazed and confused, but conscious enough to transition from being dragged to walking on his own two feet. Not sure how upset May still was, he opted to walk with Ash and Max to put some distance between the two of them. Serena quickly joined May at the front, where the two worked to finish styling their hair while discussing various fashion and travel topics.
After a while, Red decided to use the fact that the girls were occupied to his advantage. After all, he did promise Serena he would try to talk to Ash. Politely informing Max he and Ash needed to discuss something in private, he slowed down, giving a decent gap between them.
"So, Ash," he began, "as your older brother, it is kind of my responsibility to unofficially keep an eye on you. I guess the best place to start, is by asking if you have a girlfriend or boyfriend if you swing that way."
"Uh of course I do," Ash replied, "I've already had lots of girl friends and boy friends, and so have you!" Red did not quite know to respond at first, simply making an "are you kidding me" face to express his bafflement.
"Not what I meant, I meant someone that is special to you," he clarified. Noticing Ash opening his mouth and realizing where this was going, he quickly added "And no, I don't mean like mom! I mean someone that you care deeply about. Someone who you always want by your side and miss more than almost anyone else when they aren't around. Who makes you happy just because they're around."
"You mean like how May's parents care about each other?" Ash inquired.
"Yes!" Red almost too enthusiastically replied, causing the rest of the group to look back momentarily. He waited until everyone had looked away again to continue, then coughed and lowered his voice. "Exactly. Have you found someone like that yet?"
"Well, not really. I guess I've never really thought about it. Come to think of it, the last time Serena and I parted ways, she kissed me, and it felt weird, but also nice. I'm pretty sure that's just how close friends say goodbye in Kalos though," Ash answered, back to his near obliviousness.
Red's palm promptly met his face at nearly mock speed in response. Actually taking notice of his surroundings for once, Ash was confused by his brother's action at first, at least until the gears started turning in his brain. With a panicked expression, he then asked Red, "Wait!? It wasn't was it? She was trying to show she cared for me? Is that why she's been acting kind of weird the last few days?!"
Relieved that after so many years, someone had finally gotten through Ash's thick skull, Red answered. "Yes, and unless you want it to stay like that, you need to address it."
"How do I do that?"
"Well first, you need to figure out if you feel the same. Then you have to talk to her. I'd start with trying to figure out why her kiss made you feel the way it did."
Ash nodded, before rubbing the back of his head. "I don't understand most of this, maybe I should call Brock the next chance I get and ask him."
Red smirked, thinking of all the times he had seen the man tortured on their journeys while trying to profess his love to complete strangers. "That's a good idea. Just do me a favor?"
"What?"
"Whatever you talk to him about, come discuss with me afterward before you say or do anything."
After Red's outburst, a similar conversation began to take place between May and Serena. Turning to face forward again after turning around to see what the noise had been about, Serena commented. "That was odd. I wonder what they could be talking about that has him so worked up."
"I wonder if it was about me…." May began, trailing off.
"Speaking of you two, I think I should play a little matchmaker. Any preferences on how you want me to do it?"
"What are you thinking?"
"Well, I could ask him to meet me somewhere, then when he gets there have you also be there with the same excuse. Then when you both get tired of waiting for me, you can go to dinner, maybe watch a movie or find something else to do. Have a little alone time for a date," Serena speculated.
"I think that would be a little overplayed, Misty already used some of that idea to get him here in the first place."
"We could fake a dangerous situation so he'll come to your rescue or try to find someone we could use to make him jealous."
May pondered both of those before shaking her head. "No, I don't want to put him through something like that. Plus, if he were to find out he might get upset at us."
"What if I accidentally trip or shove you into him so he has to catch you?"
"How would that make something happen?"
Serena shrugged. "I don't know. I've seen it in some books and movies. It usually leads to the characters kissing. It has to work in real life for it to be used so often, right?"
"Maybe," May commented. "I'll think about that one a little more."
Serena held her chin, thinking deeply to try to come up with another idea. After a minute, she gave up with a sigh. "Why don't you just tell him how you feel and see how he reacts?"
"But what if he doesn't feel the same?" May asked. "I think I'd curl and die if he rejected me. It would be so awkward. Plus, how would we stay friends after that? I don't want to lose him completely. Also, that's a bit funny coming from you. How long have you had feelings for Ash?"
"Hey girl," Serena fired back, "do as I say, not as I do. I never said I was perfect."
Noticing they were getting close to the port, the two decided to table the conversation for another time. Seeing the ginormous boat at the dock, they gasped in awe and then stood in silence for several moments.
"If that's the boat," Serena finally spoke up, "then what do you think our first-class cabins look like?"
"I don't know," May answered, drooling a little, "but I'm sure they're amazing. And the food has to be amazing…"
"Alright guys, get ready for the most boring hour of your life," Red joked, having caught up to them while they were in their trance.
Having finally managed to board the ship, Ash and Max let out sighs of relief.
"You weren't joking earlier," May groaned.
"At least they took our luggage to our cabins for us," Serena chimed in.
"May, is that you?" A voice called out from a few feet away.
"No, it can't be," Red muttered.
"It is you!" The voice proclaimed as a certain green-haired rival came into view, his purple jacket flapping in the breeze.
"Oh my gosh! Drew! It is so good to see you!" May exclaimed, heading over to him for a hug.
"How have you been?" she asked, continuing the embrace.
"Oh, you know, always busy. It's hard work being the best," he answered confidently.
Noticing he was receiving glares when May was focused on him, he broke the embrace and quietly gulped. "Ash, Red, it's great to see you too. In fact, can I speak to you privately Red? I need your help with something personal."
"Sure," Red answered flatly, following Drew away.
Having noticed the glares as well, Serena's curiosity was piqued. "I'm going to explore the ship," she stated, quickly producing an excuse before heading away. "I'll see you guys later!"
Heading in the opposite direction of Red and Drew, she walked briskly until she was around a corner, before changing direction and darting past the group unseen. After a few minutes, she found the two males leaning against a railing on the other side of the ship.
"What do you want Drew?" she heard Red growl, clearly wanting to be anywhere but in Drew's company.
"Listen, I know we've had our differences before, mainly over May. But I want to extend an olive branch," Drew told him pointedly.
"Really?" He replied unconvinced.
"Really. Believe it or not, I've moved on from May. I even have a girlfriend. She's here too, maybe I'll introduce you two later."
"When did this happen?"
"To be honest, I tried to ask May out while we were competing in the Johto contest circuit. She turned me down and I haven't looked back since."
"Why did she do that? I thought she went to Johto to chase you?"
Now it was Drew's turn to face palm. "You idiot. She went to Johto because she was trying to get some distance from you. She thought you weren't interested in her and she felt she needed some space to get over her crush."
"Oh…" was all Red could muster in response.
"It didn't work though. If anything, it made it worse for her. That's why she went to Sinnoh to compete in the Wallace Cup. She was hoping to see you there. When she didn't, she dragged Solidad, Harley, and me around several regions trying to find you. When she finally heard you were last seen in Sinnoh, we went to compete in their contest circuit so she could look for you. Then it was on to Unova and Kalos on the slim chance you were there, but she didn't even compete in contests. She was worried it would distract her too much from finding you."
"Is there a reason you're telling me this, other than to make me feel like an idiot?" Red asked, mostly shocked at the revelations he had been given.
"I'm telling you this because I want her to be happy. You need to make a move, sooner rather than later. If you keep waiting, she's going to get frustrated and leave again." Drew explained.
"Funny, I just had an almost identical conversation with May on the way here," Serena stated, making her presence known.
Drew cursed, then fumbled to come up with a cover story. "What conversation? Are you sure you didn't mishear me?"
Red rolled his eyes at the poor deflection. "It's fine Drew. This is Serena, a traveling partner of Ash's from Kalos. She knows." Drew let out a sigh of relief.
"Since you're here, I talked to Ash on the way here. He's still pretty dense, but I think I got a few things through that thick skull of his. I'm going to give him some time to mull a few things over and then talk to him again."
"Wait, I'm confused," Drew piped in.
"Serena has feelings for Ash," Red replied without skipping a beat.
Serena punched him in the arm before hissing. "Why would you tell him that?"
"Because he can probably help us with your problem. He used to be quite the romantic when he was trying to hit on May, always sweet-talking her and giving her roses," Red told her, causing Drew to shuffle nervously.
"There you are Drew! I've been looking all over for you! You just disappeared and Red! Is that you!? It's been so long! When was the last time, after we stopped Team Galactic? What are you doing here?" A blunette with a black blouse and pink skirt called out.
"Dawn! Hey! How do you know Drew?" Red replied, embracing her.
"Well, I think I actually have you to thank." She began to answer. "After Sinnoh I decided to compete in Kanto. I ran into May and met Drew there while they were trying to find you. Long story short, we hit it off and stayed in contact. Then we traveled through Unova and Johto together-"
"And became a couple," Drew finished with a smirk. "I guess I don't have to introduce you to my girlfriend."
"Now what exactly were you two talking about, and who is this?" Dawn asked, motioning towards Serena.
"I'm Serena, I'm a friend of Ash's from Kalos," the blonde said, introducing herself.
"Who also has feelings for him," Red added, before moving to dodge another punch from Serena.
"Oh! Does that mean Ash is here too?" Dawn asked, changing the subject
"Yep. May and Max too," Red answered.
"Does that mean you finally asked her out?"
"Not quite…" Drew responded.
"What are you waiting for? Do it already!"
"I seem to be getting a lot of that lately…"
"Why are we still standing here? I want to see them! Then I am so playing matchmaker for you two!" Dawn exclaimed, heading off to search the boat for her old friends, leaving the others to follow her.