A/N: This is my first fanfic, so I don't expect it to be good, though I hope anyone who reads it will enjoy it. I do not own Pokémon or any of the characters or places mentioned. If I did then the series would've died after the first episode.

Ages:

Ash: 17

Misty: 19

May: 16

Dawn: 15

Brock: 24

–Chapter 1: Ash's Predicament–

After having won the Sinnoh League Championships, Ash was now back home in Pallet Town, where a party was being held for his victory. All of his friends were there, including Misty, Gary, Tracey, May, Max, and the others who had traveled with him and made friends with on his journeys. However, there was one thing on Ash's mind after he got back home and saw Misty, May and Dawn in the same room talking to each other.

'They're all so beautiful. I really wish there was a way for me to choose,' Ash thought to himself.

Pikachu then jumped onto Ash's lap as the boy sat on a chair, just looking at the three girls he had traveled with.

"Pika?" the small electric mouse spoke as it tilted its head at its trainer.

Ash just looked down at his Pokémon and pets the mouse's head.

"I'm fine, Pikachu. Just a bit confused as what to do right now," Ash said to his best friend.

Ash then looked just up at Misty, May and Dawn, who were still talking and laughing, apparently about when they were adventuring with Ash.

"What's wrong, Ash?" the trainer heard someone ask.

Ash turned to see the source of the voice was Brock.

"Nothing," Ash said, hoping his friend wouldn't find out what Ash was thinking.

Unfortunately for Ash, Brock's been paying attention since the start of their journey.

"You're thinking about the girls, aren't you," Brock said quietly to Ash, making sure the girls wouldn't hear anything.

Ash just nodded.

"I can see that being a problem. All three of them are beautiful," Brock said, making Ash's face turn a little red.

"But I wish there was a way for me to choose," Ash said quietly.

"Hang on. How about we talk about it outside so no one can listen in," Brock suggested.

"Sure. If anyone else hears I'd probably never hear the end of it," Ash said, agreeing to Brock's suggestion.

Ash then stood up and both he and Brock walked outside.

"I can see how you're having trouble picking one of them, Ash," Brock said.

"Really? How can you tell?" Ash asked.

"Each of them has a quality that you like. Take Misty for example. She's traveled with us the longest, through Kanto and Johto. So you practically know each other like the back of your hands," Brock stated.

"That's true. We do know each other fairly well," Ash said as he crossed his arms and started to think.

"And as for Dawn, her personality is quite similar to yours if you think about it," Brock said.

"How so?" Ash asked, tilting his head.

"Well, you both care for Pokémon and, in case you haven't noticed, the both of you can be a bit stubborn at times," Brock explained.

"I guess," Ash said as he thought about what Brock just said. "And what about May?"

"Well, it should be obvious even for you Ash. She more developed than most other girls for her age," Brock answered, causing Ash's face to turn red.

"Aside from that, Brock," Ash said, almost yelling at Brock, but remembered he didn't want to draw attention from the others in the house.

"What about her determination? Though she probably picked it up from you since you've always been determined to win the title of Pokémon Master," Brock stated.

"That's true. But those still don't help me choose," Ash said as he looked up at the night sky.

"Well, try being alone with each of them on different days. Hang out with them and get to know them more, especially with Misty and May since you haven't really seen them in a long time," Brock suggested.

"Alright. Thanks Brock," Ash agreed.

"No problem, man. You're like a brother to me, so I'll always help you when I can," Brock said.

Ash just nodded and the two friends walked back into the house. After a few more hours, most of the guests were starting to leave. But Misty, May and Dawn decided to stay so they could talk a bit more, though Misty and May wanted to talk with Ash and ask how things had been since he last saw the two of them. But before they had the chance to talk with him, Ash's mom had told them they should get to bed, since the trip to Pallet was a long one, especially for Ash, Dawn and Brock. Everyone agreed with her and headed for bed. Ash went to his room, which was kept exactly as it had been when he left for Sinnoh and the three girls shared the guest room, causing Brock to sleep on the couch in the living room.

'Okay. Tomorrow I'll spend time with Misty first since I've known her the longest. But what should I do? Guess I'll figure that one out in the morning,' Ash thought to himself before going to bed.

I know it's rather short, but I couldn't really think of anything else to add in. The girl Ash chooses will remain a mystery until the last chapter, which will most likely be Chapter 5 since I don't expect this fanfic to be very long.

Please R&R