Dean Winchester did not do feelings. He did not do 'chick-flick' moments, nor did he believe in 'heart to hearts.' Dean preferred that his emotions stayed bottled up in his head where no one could see them. He didn't need anyone to coddle him, hug him, or be his therapist. Absolutely not.

After Lisa, Dean didn't do relationships either. He couldn't afford to become attached to another person when homicidal angels were constantly haunting him. He also didn't think girls would be wooed by the pickup line, "Hello, I'm Dean Winchester. I helped jump-start the apocalypse, was almost the vessel for an asshole archangel, and might have once formed an alliance with the King of Hell. Want to go out on a date?"

Dean avoided commitment like he avoided Sam's rabbit food.

Then, one night, Sam left the bunker to pick up a library book he had on hold. He told Dean and Cas to continue researching, but Dean really didn't feel like sticking his nose in the bunker's finest dusty old textbooks. Instead, he took it upon himself to educate Cas in Star Wars.

Three movies, four beers, and two popcorn boxes later, Cas and Dean were sprawled out across the couch. Dean couldn't remember what they talked about, only that it was the most fun he'd had in a long time. In the morning, Cas hadn't left. Instead, he was sleeping, or quietly thinking with his eyes closed (since angels didn't sleep) next to him. All Dean could think was, 'I want to stay here forever.'

Thank god Sam didn't seem to notice all of these…emotions radiating off of him.

Sam would try to give him a speech about acceptance and unconditional love. Frankly Dean was not in the mood. He didn't date guys. Never once in his life had he looked at a guy and thought, 'Damn, I want to hit that.'

Sleeping with a guy.

Commitment.

Cas just had to fuck everything up.

…And Dean was okay with that.

Even though Dean avoided meaningful relationships, he'd always had the ability to charm his way in any girl's heart...or pants. Whichever worked. Maybe his tactics weren't conventional, but smiling and killing scary monsters had worked pretty well so far.

Yep, Dean thought, just keep telling yourself that. This had worked dozens of times before. Just keep smiling and trying to flirt. He'll notice…eventually.

Except he wasn't noticing! Dean had tried everything, but Cas hadn't so much as given him a second glance. Why didn't he understand Dean was trying to be his…boyfriend? No. Lover? Ew. Friends that exclusively make-out and maybe sleep together? Yep, that's it.

Dean looked across the room to where Cas was reading some obscure book Sam had given him. His eyes crinkled as he turned the page, and he snuggled deeper into the chair. He was adorable (if Dean Winchester used words like adorable, which he definitely didn't).

In that moment Dean realized he was in completely uncharted waters. Cas wasn't some random girl at bar looking for a quick fix. Cas was his best friend. If Dean actually wanted any type of meaningful relationship, he needed a new plan. A new foolproof plan to make Cas notice him.

Phase #1- Become Interested in Cas's Hobbies

This step wasn't as easy as Dean thought it would be. While they could call the bunker their home, they still often travelled from motel to motel. Cas might still have been an angel, but he had started spending more and more time with Sam and Dean. That meant Cas's hobbies were restricted to things he could pack in a duffel bag. Due to this, Cas had developed a love of readings and those stupid crossword puzzles. Both things Dean despised.

But he reminded himself of the end goal, and reluctantly picked up Cas's copy of Harry Potter. He double-checked his surroundings to make sure Sam wasn't anywhere near him. Then, he opened to the first page.

Three hours later (hours that weren't as painful as Dean thought), he felt comfortable enough to put Phase 1 into action. He waited until Sam left for a food run. He would never hear the end of it if Sam found out what he was doing.

Cas was leaning against the bedframe completely engrossed in his book. Dean paused in the bathroom to run a comb through his hair and even took the time to put on deodorant. He wanted to look presentable.

Then, he casually sat down next to Cas.

"So, what do you think of the book?" Dean asked.

Cas glanced up. "I much prefer the wizards in these novels to what exist in the real world."

"Yea, they're pretty…awesome. What house do you think you would be in? I bet you'd be Gryffindor."

Please find that flattering, Dean thought.

Cas raised his eyebrows. "I didn't know you read Harry Potter, Dean."

But you're totally impressed right?

"I got bored after a hunt, and found it in Sam's bag."

Lies, lies, lies, lies.

"I feel like I would be a Hufflepuff."

"Nah, Cas. You're too brave for a Hufflepuff."

At that moment Dean spotted a piece of Cas's hair hanging across his forehead. Before he could tell himself no, his hand was reaching out to push the piece of hair away. Dean froze and slowly drew his hand away.

Cas didn't seem to notice Dean's discomfort. He smiled at Dean with those bright blue eyes that made Dean want to wrap Cas in his arms and never let go.

"You can sit with me if you want. I found a copy of the second book at the gas station," Cas said.

Yesyesyesyesyesyesyesyes!

Dean might have spent more time staring at Cas than reading the book, but overall he considered it a success.

Author's Note

Hi! I'm back! So, I was going to make this a oneshot with all of Dean's attempts to woo Cas, but as is evident, that didn't work out. This might be updated in a couple days, but then I won't be able to update for two weeks. Curse you exams! But I shall return. I apologize ahead of time for the spelling mistakes(I can't spell). Tell me if you like it!