When Castiel asked Sam and Dean for advice on how he could express his affection towards a woman, he had hoped that they wouldn't ask too many questions. The Winchester brothers, however, both raised their eyebrows and looked at one another then back at him. They were seated in a booth at a small town diner with Dean and Sam sitting opposite of Cas.

Dean spoke first, "Got a special lady in your life, huh, Cas?" Dean picked up a fry and dipped it in a blob of ketchup on his plate.

Castiel folded his hands on top of the table, "As a matter of fact, Dean, there is a woman that I am quite fond of."

Sam pushed his mostly empty plate to the side and asked, "Anyone we know?"

Shifting uncomfortably, Cas replied, "That's not of import."

Dean leaned forward, "C'mon buddy. You can tell us."

Castiel sighed, "I really rather not."

Dean opened his mouth to say he would really rather the angel did tell them, but felt Sam's elbow digging painfully into his side. He turned and glared at Sam who ignored him.

"Well, you could just tell her how you feel," Sam stated.

Castiel shook his head, "I feel that words would not suffice for her."

Castiel looked out the window that their booth was situated by. He furrowed his brow and said, "Also, I do not feel that words would adequately give justice to how I feel about her. I would like to express my feelings by doing something special."

Dean pointed at Castiel with fry and replied, "Buy her some flowers. Chicks love flowers."

Castiel considered this. Did Meg even like flowers? If so, he had no clue what kind. "Maybe," he said hesitantly.

Sam side-eyed Dean and said, "Or you could do something really special for her like write her a poem or something."

Dean spoke, "Oh! Or you could go all Say Anything on her."

Castiel furrowed his brow, "Say Anything?" he questioned.

Dean nodded, "Like holding a boom box outside her window while blasting a love song."

Sam rolled his eyes, "Don't do that, Cas."

Castiel frowned, "Okay," he looked back out the window then back to the brothers, "maybe I could write her a song then perform it for her?"

Dean pushed his plate to the side, "Whoa there Ed Sheeran."

"Who is-" the angel started before Dean interrupted him.

"Doesn't matter," Dean said waving his hand, "if you really wanna go this whole song route, why not just do a song that already exists?"

Sam spoke, "Dean's right. There's no need to reinvent the wheel."

Castiel thought about it. He could find a song that exists and perform it for her. The angel nodded slowly, "I appreciate your suggestions," then he disappeared from the booth.

Dean shook his head, "I would pay to see how that turns out."

Sam snorted, "I'm sure it'll be interesting that's for sure."


Castiel was not one to keep up with human culture. However, over the long stint of his existence, he did occasionally check in to admire some of the arts created by humanity. Among the many musicians and singers he discovered during the 1960s when he decided to spend time watching humanity, he became quite fond of Elvis Presley. Castiel had many favorite songs performed by this particular singer, but given his goal, he knew of one song that would adequately convey how he felt about the demon.

Castiel had trouble deciding on how he would perform the song to Meg. He couldn't decide between getting an electronic device to play the music while he sang or playing an instrument while singing. Furthermore if he decided on playing an instrument, which would he play? Castiel agonized over this for days before he decided to visit the Winchester brothers.

He popped up in their motel room in the middle of the night saying, "I need to speak with you," startling both men. Both men had sat up quickly in the dark room and drew their guns from under their pillows. They blearily trained their weapons in the general direction that they heard the voice.

Castiel snapped his fingers and all the lights in the room turned on. Upon seeing it was Cas, Dean groaned, lowered his gun, and flopped back onto his bed. Sam lowered his gun and ran a hand over his face.

Dean sat the gun on the side table and pressed the heels of his hands to his eyes. He sat back up, "Really, Cas?" he growled.

Sam returned his gun beneath his pillow and looked at the clock. He turned back to Cas who stood in the middle of the room looking frustrated.

Sam ran his hands through his hair and said, "Cas, it's 3 in the morning. What are you doing here?"

Castiel shifted from foot to foot and spoke, "As I said, I need to speak with you both."

Dean glowered at the angel and replied, "And it couldn't wait until morning?"

Castiel frowned at Dean, "Well, it is morning."

Dean's mouth opened in disbelief and he looked at Sam, who coughed to hide a laugh.

"Could this wait until a reasonable hour in the morning, Cas?" Sam asked.

Castiel said, "It is rather important and I have been struggling with making a decision and wanted your input."

Sam sighed, "How can we help?"

Dean had laid back down with his arm thrown over his face, covering his eyes.

Castiel glanced between the brothers and said, "I have been having difficulty deciding between playing the piano or a guitar to perform for my…lady friend."

Dean shot back up and exploded, "Are you serious, Cas?!"

Dean looked to Sam and asked, "Is he-" Dean closed his eyes for a few seconds and opened them gesturing to Cas, "Are you hearing this, Sam?"

Sam, who was biting the inside of his cheek and trying to keep a straight face, lost it. He dropped his head into his hands and laughed. Dean, who was beyond irritated, watched his little brother laugh, uncover his face then wipe tears from his eyes. However, when Sam looked over at Dean's scowl, Sam's face wobbled and he started laughing again. Sam would later explain to Dean that it was the lack of sleep and Dean would grunt, 'Whatever.'

While Sam was composing himself, Castiel turned to Dean and asked, "Guitar or piano?"

Dean, who was still scowling at Sam, looked back at Castiel. He shifted his jaw back and forth, realizing he had been clenching over the past few minutes.

"Cas, man, can you just come back an-" Dean stopped, seeing the determination in the angel's eyes. Dean sighed, "Fine, guitar."

Castiel looked at Sam and said, "If you're done, Sam, what would you recommend?"

Sam who was still snickering and trying to catch his breath huffed out, "Guitar. Guitar would be ideal."

Castiel nodded and replied, "You both have my thanks," leaving the brothers in a flutter of wings.

Dean laid back down saying, "Sam, can you get the lights?"

Sam grunted, left his bed and turned off lights Cas had turned on in the room. By the time, he returned to his own bed, he could hear Dean snoring softly.


Castiel spent weeks learning to play the guitar and then finally the song he wanted to perform for Meg. He then realized he had to not only teach himself to play and sing simultaneously, but to sing on key as well. Much to the angel's chagrin that last bit pushed his performance back another few weeks. When the day came that he believed he was ready to perform the song for the beautiful demon, he snagged a bouquet of daisies from a flower stand. Chicks love flowers, Dean had said. He thought maybe it would be good to take pointers from both Sam and Dean.

Castiel arrived at the apartment that Meg had taken residence. He had an acoustic guitar slung across his body and his left hand held the flowers. He shifted the guitar and knocked on the door. After a bit, the door opened to Meg smirking.

"Well hello, Clarence," she said, eyeing the flowers.

"May I come in?" Castiel asked.

The demon stepped back opening the door for Castiel. Castiel stepped into the loft and Meg closed the door behind him. She watched as Castiel looked around Meg's most recent apartment.

Castiel cleared his throat, "Your home is very nice."

Meg moved to stand beside him and tilted her head looking around the space, "It gets the job done."

Meg turned and looked up at the angel's face, "What brings you here, Clarence?"

The angel had spent the better part of two months coming up with excuses to visit the demon and spend time with her at least once a week. Castiel's reasons for visiting ranged from asking questions about humanity that he didn't actually care about and asking about lore that he already knew and suspected she knew he was already knowledgeable about.

The angel shuffled his feet and held the bouquet of daisies out to the demon. He said, "Well, uh, these are for you."

Meg arched an eyebrow, "For me you say?" she said as she took the flowers.

Castiel brought the guitar in front of him and replied, "Also, if you'd please take a seat, I'd like to perform a song for you."

Meg raised her eyebrows in question. Castiel nodded towards the stools situated at the island in the kitchen nearby. Meg grinned, walked over and sat on a stool with her legs crossed, holding the flowers.

Castiel cleared his throat once more. The angel began strumming the guitar and singing, "Wise men say only fools rush in," and he looked up at Meg, "But I can't help falling in love with you."

Meg lifted the bouquet of daisies to her face and smiled into them. After Castiel finished the song, he spoke, "I wanted to express how I felt about you so I thought-"

Meg stood up from her stool and walked over to the angel. The demon raised herself onto her toes and pressed her lips to Castiel's silencing him. She then said, "Why, Clarence, you sure do know how to make a girl's heart flutter."