Ash and May have dated for a few years as they started to travel together after Ash's journey in the Kalos region. He traveled with new friends Clemont and his sister Bonnie along with a friend he met years ago, Serena. They all had fun together and at the Pokemon League, Ash was runner-up for competing in the league. So after the league was finished he went home, but he was surprised that Serena said to him that she liked him. He didn't want to hurt her feelings but he had explained that May was his girlfriend and that he hopes that they can still be friends.
Serena was surprisingly calm and accepted his offer of friendship; soon afterwards they all went their separate ways. Then Ash and Pikachu went home to Pallet Town only to be surprised that May was there to greet them. She proposed that they travel together through the Indigo League again and she would compete in the contest circuit again.
Now they are in the Hoenn region again after Ash had won the Indigo and Silver League in Kanto and Johto. Now he was challenging the Hoenn league and May was competing in the Hoenn contest circuit after taking a year break from when they were in Johto.
Currently, they were in Slateport City where May was training with her Pokémon, improving any new combinations that they came up with, while Ash and Pikachu were watching them working. Now Ash was about 18 years old with May being 17 years old. He watched at her progress and smiled at how well she improved her skills over the years.
He interrupted by saying, "Hey May, why don't we call it a day. It's starting to get late and we have to get ready remember?"
Tonight was their anniversary of three years and he had something special in mind for tonight as a surprise.
May smiled and replied, "Yeah, I remember silly. How could I forget?"
So they headed back inside the Pokémon Center and they had gotten ready. Ash went first and was relatively fast as he let May gave the bathroom to her while he got ready in the room. He wore a navy blue button-down shirt with black slacks and black dress shoes. He actually attempted to comb his hair and he put on cologne as well.
He looked at himself in the mirror and then turned to Pikachu and asked him, "Do I look okay, buddy?"
"Pika pika,(You look great.)" Pikachu answered honestly.
Ash smiled at Pikachu and proceeded to sit on one of the beds and waited for his girlfriend to come out, when she did, he was stunned. May was wearing a blue strapless dress that was a bit above her knees with strappy blue sandals. She wore the locket that Ash gave her those three years ago that went well with her blue dress and her eyes. She wore a bit of light blue eye shadow and light mascara to make her eyes pop. Her hair had been curled at the ends and fell past her shoulders.
She smiled at him and asked playfully, "How do I look, Ash?"
He snapped out of his trance and answered, "Beautiful, as always."
She had blushed slightly with the biggest smile she could muster and then she asked, "Shall we go?"
Ash nodded, held out his arm and then she latched onto, smiling brightly. They left Pikachu and Glaceon to relax in the room and them spending time together as well.
They headed to a nice restaurant that May recommended they should try. Ash had made reservations two days before and they were quickly seated because of their status. So they both ordered their food and they had a good time like they always do. By the time they ordered dessert, it was already 10 at night. So they waited for their dessert and they were discussing their plans on where to go next. Their dessert came and they ate together, fully enjoying their dessert.
Until suddenly, Ash rose up from his seat and gathered the attention of all the other customers.
Ash spoke loudly, "May I have everyone's attention please?"
All of the guests turned their heads in the direction of their table and May looked at him in confusion. Ash turned to May as he said, "I would like to say something."
He walked around to May's side of the table and she continued to question his reason for doing this.
He smiled down at her and he looked in her eyes as he said, "May, we have been dating for three years and I can honestly say that it has been the happiest three years of my life. I've been thinking this over for a long time now and I came to the conclusion that I always want you with me by my side."
He gently held her hand and he kneeled down on one knee, causing May to gasp in shock, covering her mouth with her free hand.
He squeezed her hand as he added, "May, you have always been there for me and I love you so I only want to ask one question."
He let go of her hand momentarily to pull something from his pocket and in his hand was a velvet black ring box. He opened the box to reveal that within was a silver ring with a heart cut sapphire with two diamonds on the each side.
Ash looked lovingly at her and asked, "May Maple, my Princess, will you marry me?"
May's eyes were tearing up and she smiled in happiness that she whispered happily, "Yes Ash, I will."
He put the ring on her ring finger while May pulled his face towards her and she gave him a loving kiss on his lips as the people around them cheered.
Ash had the biggest smile on his face as he held May in his arms as they sat on a bench in a park after they left the restaurant. They were looking up at the sky, just at ease with each other's presence. May had fallen asleep as they were watching the stars and he brought her closer to him. He thought that he'll tell his mother in the morning that he proposed and May will tell her parents and Max as well.
But for now, he put his chin on the girl's head and smiled in content, thinking of their future and how they will be happy together. He closed his eyes and had happy thoughts of himself and his Princess in his arms. He had been lucky to have her and he was glad that he went with what his heart wants and he wanted to be with May for years to come. And for that, he was grateful.
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