Review (up to 06/09/16) replies in the Author's Note at the end!

Disclaimer: I don't own Pokémon.

Ash groaned as he started to regain consciousness, rubbing his eyes, he could feel a slight throbbing in his head. Memories of the night before started flooding back to him, and the aching started to subside. His heart rate quickened as he remembered saying goodnight to May, but as quickly as that feeling came, it was replaced by guilt. He frowned.

Ash reached over and grabbed his phone from the bedside table. 9am. He opened his text messages and typed out a reply to Brock's message from the previous night.

"Hey man, is alright if Pikachu and I come over for some breakfast, and for that catch up you wanted?"

Ash only had to wait a few minutes before he got an affirmation from Brock. Not feeling like showering just yet, he threw back on the clothes he had worn the night before. Pikachu had started to stir whilst Ash was dressing.

"C'mon buddy," Ash said softly, "we're heading over to Brock and Misty's for breakfast." Pikachu smiled widely, hopping onto Ash's shoulder. They went downstairs and Ash walked over to one of the worktops he had in the kitchen, and grabbed a set of keys, knowing that it was far too early for a drink, and knowing he had to go to the airport later, he decided to drive to the bar.

-IBYL-

"Well hello there, lover boy," Brock teased, as he opened the door for Ash. The latter rolled his eyes.

"Very funny," Ash deadpanned, brushing past Brock, "we just went somewhere we could talk easier." Brock smirked behind Ash's back.

"And what exactly did you and May talk about?" Brock asked. Ash sighed and pinched the bridge of his nose.

"I'm 25 years old and I'm being treated like a teenager," he mumbled, walking through the bar and into the residential area. "Don't you start!" Ash exclaimed, pointing at Misty as he walked in, seeing the teasing look that had formed on her face. Misty, Brock and Pikachu all burst out laughing

"C'mon, Ash, at least give us something?" Brock pleaded, as they all sat down and tucked into their food, "it was really good to see you genuinely smiling."

"Yeah, well, the smiling was just a cover to hide all the guilt I'm feeling," Ash snapped, catching the trio off guard.

"Ohh… Ash…" Misty said sadly, "we're sorry, we didn't mean to offend! We know it's the anni-" Ash cut her off by bursting out laughing himself. Brock and Misty glared at him, having genuinely thought they'd upset him.

"I told myself I'd get you two back for your little wager last night," Ash said smugly, folding his arms cockily across his chest. He then frowned. "But in all seriousness, May and I had a wonderful time."

Brock and Misty smiled at each other.

"There was a genuine connection there," Ash added, leaning back in his chair as he reminisced, "a connection I haven't felt since… Serena," Ash whispered his name. Five years on and it still wasn't any easier. The couple shared a look at Ash's words.

"So, are you gonna arrange another date with May?" Brock asked, trying to take the conversation away from the sad topic. Ash thought about it.

"I don't think so," he said quietly. Misty shot upright in her seat.

"Why not?" she screeched, causing the guys to cover their ears, "you just said you felt a connection?!"

"Woah! Why are you getting so agitated about my dating life?" Ash shot back, feeling fed up with people telling him what's best. Ash sighed as he noticed the look Brock and Misty had shared. "What haven't you told me?"

"Umm…" Misty stammered, "May and I have been friends since childhood… I kinda invited her along once I knew you were coming, I was hoping you two would pick each other out." Ash couldn't say he was surprised, he'd had a feeling they'd pull a stunt like that.

"She mentioned she grew up in Cerulean, before moving to Hoenn," Ash replied, remembering the conversation he'd had with the beautiful brunette.

"We stayed I touch even after she moved out there, turns out she started her journey whilst we were in Johto," Ash raised his eyebrow, wondering why Misty was bringing this up, "you would've met her in Hoenn had you gone there a year earlier."

A comfortable silence enveloped the group as they ate their meals.

"In all seriousness, Ash," Brock started, grabbing the Gym Leader's attention, "what's holding you back? It was plain to see that you saw something in May last night." Ash thought about it.

"I-I'm…" Ash stuttered, before sighing heavily, "I'm afraid." Brock and Misty shared another look.

"Afraid of what? Getting hurt again?" Misty asked gently, trying to prompt Ash to open up, but as May had said the night before, it was like trying to get blood out of a stone. Silence once again fell over the group.

"Partially," Ash answered quietly, "what if she doesn't accept my situation? And I keep getting these feelings of guilt when I notice how I'm feeling about her." The couple pondered Ash's words.

"Well, knowing May as I do," Misty started, "I reckon she'd understand your situation." Ash raised his eyebrow.

"Reckon? I don't want to take the risk," Ash replied, in a tone that almost killed the conversation.

"As for the guilt," Brock said, looking Ash dead in the eyes, "you have to get past this, no matter how hard you find it." Ash took the words in, but he'd been trying to get over it for five years, and had no luck so far. He glanced at his watch.

"Crap! I need to go to the airport!" Ash said, a tone of excitement creeping into his voice, "thanks for the food, guys, and the advice, I'll think about it." Pikachu hopped onto Ash's shoulder and waved at Brock and Misty as the raven-haired trainer rushed out of the building. "Hey mum, I know we arranged a dinner tonight, but would it be okay to rearrange for later this week?" the couple heard Ash say on his way out.

"I really hope he gets past it," Misty said quietly, as she and Brock started to clean up, "I think they could really help each other get over their history."

Brock nodded, "I can't get over how good it felt to see him smiling again… Ever since Serena…"

The words hung in the air. They had just finished cleaning up in silence, when there was another knock on the door. This time Misty went to answer it. She opened the door to reveal a brunette wearing a red and white bandanna, along with a red top and black mini skirt.

"May!" Misty said excitedly, as the two embraced, "it's good to properly see you!" May giggled slightly.

"You too, Misty! It's been far too long since we've just sat down and talked!" Misty smirked slightly at this.

"I'm guessing you're here to talk about last night?" She asked, winking at May. The latter blushed profusely, and nodded meekly. "Well come on in, Brock's in the back." The two walked through the bar and into the room that they had just eaten in.

"Hey, May!" Brock greeted, also giving the brunette a hug, "we just finished eating, can I get you anything?" May shook her head.

"No thank you, Brock, surprisingly, Max cooked breakfast for us this morning," May replied, "which was a shock, to say the least."

"How's he doing? I heard he gave this one a beating the other day," Brock teased, jabbing a thumb in Misty's direction.

"Watch it mister!" the red-haired warned, causing May to giggle.

"He's doing well, that was his seventh badge," May answered, but then a confused look settled on her face, "he never actually mentioned how he got on with the Gym here, he just asked if we could train later."

Brock and Misty shared a look. Had Ash not told her he was the Gym Leader? May seemed completely oblivious to the matter.

"That's good to hear," Brock replied, "and how did you find last night?"

The couple smirked as May flushed red.

"I had such a wonderful time," May gushed slightly, "Ash was such a gentlemen, and he has an incredible sense of humour! I'm so glad you advised me to come, Misty." The latter smiled at the brunette.

"I'm just glad you've enjoyed yourself," Misty said, "even more glad now that you're regions away from that scumbag." May frowned, before letting out a sigh of relief.

"Me too, Misty, me too," May muttered, "there was one thing about last night though."

"What's that?" Brock asked, noticing the frown return to May's face.

"Ash didn't really talk about himself much," May answered, "he seemed quite secretive, and very reluctant to talk about his past, even when I tried to comfort him." May sounded downhearted as she spoke. For the umpteenth time that morning, Brock and Misty shared a look.

"I know you can get through to him, May," Misty said, smiling at the hopefulness that crept onto May's face at her words, "if you would like a future with him, just spend more time with him, he'll open up eventually."

May's smile slowly widened as Misty's words sunk in.

"Thanks guys, I needed to hear that," May thanked, "I don't know how or why, but it just feels like I've known him my entire life, I've never connected so easily with someone before."

The couple smiled at May, knowing that Ash had felt that same connection.

"I best get a move on, don't want to keep the brat waiting for his training!" May joked, and the three shared a laugh. They all hugged again, saying their goodbyes.

"Hey, May," Misty said, as May stepped outside the door, "Ash has had kind of a rough deal, he just needs some gentle encouragement." May smiled at Misty's words.

"Thanks, Mist," she replied, "ohh, and thanks for arranging the event last night!" the couple could tell she wanted to say more, but she had decided against it.

"Bye, May!" the brunette waved as she walked down the street.

-IBYL-

Ash laid his head back against the headrest of his car, eyes fixed on the road. A frown formed on the Gym Leader's face. The guilt was back, and this time, he had no one to hide it from. A low groan slipped out of his mouth.

"Why am I feeling guilty?" He mumbled to himself, "its been five years since Serena…" he gulped, just saying her name made his heart ache.

"Pull yourself together!" Ash scolded himself. The feelings were eating away at him, they had been slowly for years. But now? They seemed to be doing it quicker since meeting May.

The thought of the brunette made a smile flicker onto his face briefly. As quickly as it had come, it was replaced by the guilt and heartache.

Ash growled as he arrived at the airport. He sat momentarily, before forcing the issues into the back of his mind.

-IBYL-

It had been a few days since Max had lost at the Gym, and having spent most of the time since training – either on his own or with May – he felt relatively prepared as he climbed the stairs to the Gym, with his sister in tow.

"So you reckon you can beat him this time?" May asked, a slight teasing tone in her voice. Max shot her a glare over his shoulder.

"I hope so," he answered, "I might stand a chance if his other Pokémon are weaker than that Charizard."

"What typing does he use?" May asked, speeding up so she was walking next to her younger brother.

"That's the thing," Max replied, "he doesn't use a set typing." May's eyes widened.

"How will you be able to beat him not knowing his type?"

"He reveals his Pokémon first."

"I s'pose that makes it a bit fairer," May surmised, as they reached the door. They pause for a moment as they hear a voice coming from the back of the building. Max knocked on the door, and they waited patiently. The voice continued. May huffed slightly and rang the doorbell. The voice stopped, and they could hear a door sliding open.

May gasped inaudibly as the door swung open. "Of course!" she thought, "how did it slip my mind?!"

"Hey, Max," Ash greeted, as he realised who was in front of him, shaking Max's hand, "here for your rematch?"

Ash's eyes flicked to the person stood behind Max. His heart jumped into his throat.

"No, no, no!" Ash thought, managing to keep a smile on his face, "not like this…"

"Hey, May!" he said, making sure sounded enthusiastic, "I'm guessing you're the sister Max mentioned last time he battled?" Ash asked, as he stepped forward and greeted her with a hug. She quickly got over her shock and hugged him back briefly.

"You two know each other?" the siblings asked each other, in unison, once the hug had ended. Ash raised his eyebrow, amused.

"Did you two not talk about our match at all?" Ash asked, his amusement creeping into his voice, "Max challenged me and briefly mentioned he had a sister, and May and I met a couple of days ago at some friends of mine's bar," Ash explained, he gestured to the inside of his house, "would you two like to come in?" Max shook his head.

"Thank you for the offer, but I think I'll leave you two to it," he answered, "I could use some more training before I actually challenge you again." Ash nodded in response, before turning his attention to May.

"The offer still stands?" His heart pounded as he awaited May's answer.

She smiled brightly, "I'd love to."

"I'll catch up with you later, May," Max said, as he turned to leave, "I'll be back to challenge you again soon, Ash." Max smirked as he turned his back.

"See you later, Max!" Ash and May said in unison, causing them both to blush slightly. Ash holds his arm out, gesturing inside once again.

"After you, madam," He said, smirking and bowing slightly.

"Why thank you, good sir," May joked back, giggling slightly as she spoke. Ash smiled as he followed May in.

"Can I get you anything to drink?" Ash offered, heading over to the kitchen, whilst May took a seat on the sofa.

"Just a soft drink, if you have one," May answered, skirting her eyes around Ash's home. There was a large coffee table in the middle of the room, with sofa's either side. Directly behind these were a set of sliding, glass doors, which May could see led out onto the back of the estate. There was another sofa, which had a smaller coffee table in front of it, just to the side of those doors, aiming to May's left, where there was a large plasma TV on the wall. Diagonally left, and below, the TV was a fire place, with a large mirror above that. On top of the fire place, she could make out what appeared to be picture frames, lying face down. Just to the left of that was a narrow entrance that seemed to curve around, with stairs there.

May glanced over to the direction Ash had gone. There was a worktop directly behind the sofa, as the kitchen and the living room were connected, with a gap in between the "sofa worktop" and another, larger worktop that stretched across the rest of the room. There was no real wall, so May could see Ash moving around the kitchen. There was a breakfast table in the middle of the kitchen, and on the far side, there were cupboards up along the wall. She watched Ash walk to the fridge, which was in line with the sofa that faced the TV. He pulled out a bottle of soda water, and a fresh lime. He poured some lime cordial into two pint glasses, followed by the soda water. He quickly and efficiently sliced up the lime, and with a quarter of it in each hand, he squeezed them into a glass each, before dropping the lime in. He placed the rest of the lime back in the fridge, shutting the door afterwards. Ash grabbed the two glasses, and pushed them up against the fridge door. A couple of ice cubes dropped into the drinks.

"Thank you, Ash," May thanked, accepting the drink.

"I hope you like lime and soda," Ash said, taking a sip of his, "I just find it much more refreshing than cola or lemonade." May smiled.

"I agree, I'd say it's my favourite soft drink." Ash smiled at that, it was his as well.

"So, you forgot I was the Gym Leader?" Ash teased, as the two sat down on the sofa by the sliding door. May blushed slightly.

"It may have slipped my mind," She mumbled, sheepishly rubbing the back of her head. Ash chuckled.

"It's okay, I don't like to brag about it too much," Ash said, "I've found it brings the wrong kind of attention."

May understood that feeling. So many times she had been approached by men who just wanted to get to know her because of her success.

"I understand that," she voiced her thoughts, "I've had plenty of attention, just because I won a Grand Festival." She made no attempt to hide the disgust in her voice. Ash nodded in agreement, people who mocked him for his poor display in the Kanto League quickly tried to get into his good books after he beat the Johto League.

"I was thinking, Ash," May's voice snapped him out of his thoughts, "when did you travel to Hoenn? I can't believe I would have missed your battle with my dad." Ash considered this.

"Well I saw Misty the other day, and she happened to mention that you left for your journey the year before I travelled to Hoenn," May nodded, and watched Ash expectantly, wanting him to tell her more about his journey, he obliged, "I started my journey at 10, it took me a year to go through Kanto, and then a year and a half through Johto."

"I was 10 when I started my journey as well," May commented, she worked out, from the information, that Ash must be 25. They'd never actually told each other their ages.

"So that means you're… 22?" Ash questioned, feeling a bit stupid for not asking sooner. May smiled at their synchronised thinking.

"Actually, I'm 23," May answered, "it would've been easier for me to say I was almost 11 when I started my journey, my dad was reluctant to let me leave," she pondered this for a moment, "we still would've travelled Hoenn at the same time, if that were the case?"

Ash thought about that, "I took a break after beating the Johto League, I wanted to let the excitement die down before travelling again," he explained, "I'm 25, by the way," he said, smirking.

"I figured that out myself, thank you!" May teased, winking at him. The two shared a laugh. When they had settled down, May gestured for Ash to continue telling her about his journey.

"Ohh!" He exclaimed, realising he hadn't finished, "I then spent a year in Hoenn and Sinnoh, I actually spent two years in Unova, and then my last journey was through Kalos, which was also around a year," Ash finished, mentally counting the years that he had been on the road, "I also spent six months taking on the Kanto Battle Frontier."

May's eyes widened in surprise, "that's a lot of travelling!" Ash smiled slightly.

"I think that works out as being on the road for… Eight years?" Ash roughly estimated, "I decided to settle down slightly when I was 18," he added, "I took on various other challenges that people offered me until I was 20, when I became Gym Leader." May's eyes widened in surprise.

"You were the Gym Leader when you were 20?!" May exclaimed, Ash nodded in response. May was very impressed at that, even though she'd known other Gym Leader's to be younger, she was well aware of Pallet Town's reputation of being the strongest in the region. "By the way, you have a really lovely house," May complimented, gazing around the room again. Ash smiled.

"Thank you, May," he replied, "this actually used to be Professor Oak's laboratory, but it so happened that I got the role as Gym Leader at the same time that he upgraded to a bigger facility, so I bought it off him, and converted the lab into a living space, and built a battlefield for the Gym just outside," Ash explained, pointing out of the back door to where he and Max had fought the other day.

"That's awesome! You've done a really nice job with the place!" May complimented, still looking around the room.

Ash gulped quietly as the guilt settled on him again. "Serena did most of it…" he thought. He took a large swig of his drink, trying to snap himself out of it. It wasn't fair to May.

"Would you like a top up?" Ash asked, standing up to head to the kitchen.

"I'm alright for now, thank you," May replied, she was amazed at the décor of the place, trying to imagine what it was like here when it was Oak's lab. Ash smiled at the look on her face, before turning to make his drink.

May's eyes settled on the larger coffee table in the middle of the room, and something caught pink caught her eye. She walked over and felt her stomach drop.

Ash mentally kicked himself as he made his drink, his back turned to May. "Pull it together, Ash!" he scolded himself again, "Five years!" it had become a mantra to him. He finished making his drink and turned to walk back into the room. He froze in his tracks as he saw May.

She was holding a pink hairbrush. Ash's heart leapt into his mouth.

"I knew this would happen," Ash thought, "why didn't I make an excuse?!"

He sighed, dejectedly.

"I guess I should explain," He said, walking over to the coffee table they had been sat by, placing his drink down. Ash then made his way over to May and gently took the hairbrush from her. He looked at it momentarily.

"You don't have to explain anything, Ash, I just assumed you were single, attending a speed dating event and all, but -" May said quickly, trying to hide her disappointment and pain. She quickly moved back over to the other sofa and took a large gulp of her drink.

"No, no, no!" Ash rejected quickly, moving over and grabbing May's hand, guiding her to sit down next to him, "it's nothing like that." He squeezed her hand at attempted reassurance, May met his eyes, and a huge wave of guilt crashed over him. She looked so hurt.

"Somebody has done that to her before," Ash figured out. His feelings turned to anger. "How could someone treat this amazing, beautiful, funny woman in such a way?"

The way he had thought about May made his anger turned to guilt. He couldn't hide his pain this time.

May watched Ash closely, and notice him physically wince. "Whatever he's trying to say, it must be really tearing him up inside," May thought. She then remembered what Misty had told her earlier.

"Ash has had kind of a rough deal…"

"Umm… y'see… I… I…" Ash's stammering brought May out of her thoughts, and the look on his face melted her heart. She shifted her hand, which Ash was already holding, so that she could interlock their fingers, giving his hand a gentle squeeze.

"Ash, if it's too har-" May attempted to comfort Ash, and reassure him that he didn't have to tell her if it was too painful, but Ash cut her off, having been given the strength to tell her by her actions.

"I have a daughter."

EOC

So there it is. Ash's secret is out! How will May react?

A slightly shorter chapter, but I feel there was more development in this one than Chapter 1, and feel happier about this one. Hopefully you all enjoy it as well!

I've added a bit more of the slight AU background there, with more to come in the next chapter.

Thank you to each and every one of you who favourited and alerted to the story! It had a much better reception than I had expected!

As for length of this, I have one more chapter roughly sketched out, and the possibility for a fourth, but at this moment, I can't see it stretching much further than that. I have a couple of other small projects I would also like to work on, but being a stereotypical guy, I can't juggle them both at once!

REVIEW REPLIES:

WHAT IS MY THIS: I really appreciate your kind words! Grammar is a very big thing for me, I can't count the amount of stories I've read on here that have very good plots, but are ruined by poor grammar. A pet peeve of mine, so I'm really glad you think mine was good! I hope the plot holes were rectified somewhat here, they were slightly intentional, to try and keep readers hanging!

PRAETORFABLE: Familiar face number 1! Thank you so much for your review! That means a lot to me! I hope you enjoy this chapter too!

ABOZ567: (Familiar face number 2!) I'm really grateful for you reading this, and grateful for the review you left on If You Could See Me Now, it's astonishing and heartwarming to see a familiar face to my stories. It's great to be back! Thank you! As I mention before, a couple of more chapters for sure, but once I've finished what I planned for this story, I'd be happy to try and create some "oneshots" carrying on in this universe! And might I add, I am really, REALLY, enjoying "How to Change a Life," I'll be completely honest, reading your story helped me get motivated to start re-writing again!

KODAKOHL: (Familiar face number 3!) And as I said above, I'm so grateful that you're still a fan (if I may be so bold as to call you a fan), as with grammar, details are another big thing for me. I like to think I have a vivid imagination, and want to be able to present exactly what I'm imaging to the readers. As for Ash and May knowing each other… I lot of that is to do with their pasts. For this fic to go the way I'd like it to, I needed them to have not travelled together. The "recognising" each other was kind of a last minute idea, just to add a bit more of a connection between the two.