"Look, I don't get it." The boy said, shaking his head as his friend as he rooted through a pile of clothes. 
"Get what?" His friend responded, only looking up at him momentarily before pulling out a t-shirt that looked dirty from being worn for a week and throwing it aside.
"Why you're trying so hard to impress this girl. She doesn't even dress up like the others. She doesn't care if you wear your dirty work clothes, most likely." He replied, laughing at his friend's struggle. He paused and stopped rooting, sighing.

"...You don't get it. She has this air to her like she doesn't really care about anyone. She just... looks right past you. How am I supposed to impress her? Get her to even look at me?" He asked, defeated, and fell as he laid over on the pile of clothes. 

His friend laughed and helped him up. He shook his head at him for acting so odd, then started to leave.

"Look, Jake, you're going crazy. No girl is worth digging through a pile of months old clothes hoping to find a clean shirt." He said, then waved.
"I've got an art class to go to. Good luck, Romeo." He said sarcastically.

Jake watched him leave, then sat on his bed and put his hand to his face. He looked at the mess of his room and reached over to his side table and grabbed through his drawer and found a wallet. He took out his phone, looking at the options he could find at the mall. When he finally convinced himself he got up and grabbed the keys off of his shelf and walked outside to his beat up car.

When he finally got to the mall, he searched for a store that had (in the very least) something other than sports gear for men. When he finally found a store, he shopped valiantly for something that screamed 'please like me'. Feeling a little desperate about how he had just thought that; he shook his head for a moment before grabbing a few more shirts and clean jeans that weren't ripped (that badly). He paid for it as he found the total to be $300, cursing himself as he felt like he was wasting his hard earned money. 

And as he started to head to the shoe store, he felt a bump against his side as his bag rustled and heard a startled noise. A girl, straight faced and wearing a band t-shirt looked at him. He mumbled under his breath and then apologized.

"...Yeah. It's fine, I guess." She said, shrugging. She looked a little bit more aware of who he was in a moment and lightening up a little.

"Wait, Jake? Wow! Didn't see you as the type to be planning a new wardrobe like that. You've worn the same shirt for at least two years." She said, a little bit sarcastically.

The interaction in itself was enough to make him speechless, as Cassie really wasn't the type to talk much. In fact, this might have been the second time she had ever really spoken to him. 

"You noticed that? Jeez..." He said, trying to get words out.

"...And... I have a pile the size of a mountain in my room of dirty and small clothes. So it was completely clean my room or buy new clothes for the school year coming next month." Jake said, laughing nervously.

"That's not lazy at all!" Cassie said, smiling. She went on her own way and Jake watched confusedly.

It was entirely stereotypical, he knew, to say that girls were confusing. In fact it was so stereotypical that he had to pause for a moment to shame himself.

But none of that mattered, because he was going to buy a new pair of shoes and go home and wonder what would come next. A month couldn't go by faster, and there was no way that he could interact with Cassie outside of school.

He would have to find out in a month what was coming.