Hiya! This story means more to me than some of the others I've written, mainly because it is based off of my personal experiences. My goal for this is to express how I felt through Jessie in a way that others might relate to as well. Some things will be similar to my experiences, while others won't. I'll be posting a chapter a day except for chapter twelve, which will be posted whenever I get it done. Hope you enjoy! Leave a review!

Summary: Feelings are confusing sometimes. When you truly love someone, you want them to be happy no matter what, even if it means hurting yourself in the process. Jessie learns this after helping James with his love life. ROCKETSHIPPY!

It was an ordinary day, just like any other. James, meowth, wobbuffet and I were selling our homemade malasadas. It wasn't a very busy day, so we had quite a bit of free time between costumers.

I was just relaxing when another costumer came. She was not one of our regulars, in fact I don't think I'd seen her before. She looked to be about our age. She was short, had auburn coloured hair, freckles, and bright blue eyes.

From what I could see, James couldn't get enough of her. As he took her order, he was in some kind of trance. He was fumbling his words and blushing a lot. This behaviour was very out of the ordinary, and only meant one thing- he liked her.

Now, let me tell you, James was not the kind of guy to just fall for somebody so easily. His childhood experiences with Jessebelle have caused him to completely close himself off from love... until now. I couldn't help but smile as I watched him make a complete fool out of himself. It made me happy seeing him so happy. And it was nice to see him opening up despite his past.

Meowth was also finding the situation quite amusing. He kept looking at me with a bewildered expression, as if to ask is I was seeing what he was seeing.

Oh yeah, I was seeing it. That girl had a certain look in her eyes, bright and happy but at the same time deep and questioning. It seemed so familiar, but yet I had no idea where I had seen it before. She was definitely interested.

After giving her the malasada she ordered, he also gave her a free one. I was going to tell him off for the freebie, but something stopped me.

The mysterious girl then left. Just like that, the moment was gone and James was watching her leave sadly, never to be seen again. Not if I had anything to do with it.

"James, we're closing early tonight. You are going to talk to that girl." I say. Meowth is shocked for some reason.

James started blushing profusely. "What? Why?"

I smirked at him. "Oh, I think you know why..."

"I'm not going to ask that girl out."

I couldn't believe what I was hearing. "Why not?"

James thought for a minute. Why not? "B-Because I'm not as confident as you are! I can't just go up to her and ask her out!" I looked at him with disbelief. If he liked her, he should just go up to her and ask her out. Surely she'd say yes if she liked him back, which she did. As if reading my mind, James blurted out: "fine." He then quickly left our malasada stand and started following the girl, as she was almost out of sight at this point. He managed to stop her and the pair was just barely visible to me.

I watched them as best I could from where I was. I couldn't hear what they were saying, but the conversation went on for a solid five minutes. This was a good sign. They eventually parted ways and I noticed James doing his cute little happy dance as she left. A very good sign.

He practically skipped back to the truck, his face a very deep shade of red. I laughed at him a for a moment before asking him how it went.

"Oh Jessie it went amazingly! We have a date tomorrow evening!" He said excitedly.

"Yay!" I say. "You're probably the only guy on this planet who could get a date in that outfit." I motioned to his bewear inspired uniform.

"Hol' on a second..." Meowth thought for a moment. "You're leavn' tomorra? Friday? Teh busiest day uddah week?"

"Yes Meowth, and you don't need to make him feel bad about it." I told him. I wasn't super enthusiastic about it, but I actually wanted to give him the day off, so he could have all the time he needed to prepare.

"Here" I handed him our wallet, which contained all of our small amount of money. "Buy yourself something nice to wear." I said. This whole situation made me so happy, I love love! James was finally ready to start dating again, and that girl seemed perfect.

Understandably, he looked a bit confused, as it wasn't like me to give James control over our money, unless it was for a pikachu plan. "You sure? Thank you so much!" He took the wallet and hugged me. "I gotta tell you more about her, she's great!"

He spent the rest of the evening talking about her. Apparently her name was Jenn. James would not shut up about how pretty she was, and how pleasant she was to talk to. She was pretty. She had a unique type of natural beauty that I don't really know how to describe. James has a great taste in women.

I continued to listen to him ramble about Jenn and about how thankful he was for the entire balloon ride back to home base, until we finally arrived. Then, the conversation shifted to starting a fire and getting some shuteye.

That's it for now! Hope you enjoyed this so far! Expect updates daily!

Luv ya!

Buh-bye!