After that moment on the hiking trail, Dean never left before telling Castiel he loved him. Dean was over at his house a lot. After he got off work, he went straight to Castiel and Gabriel's house to check on them. It wasn't until late that he would leave. Dean sometimes took time off work to take Castiel to his appointments so Gabriel could have some time to himself and even started helping them pay the bills.

Gabriel loved it when Dean was over. He loved seeing his little brother with someone who could make him so happy, especially when depression could've taken that place in Castiel's heart.

Dean didn't only spend time with Castiel. He came in every morning to the coffee shop to check on Gabriel and see how he was doing.

Gabriel was doing better. His boss insisted on a raise after the old woman complained to him that he wasn't paying him enough (the old woman came by Winchester Motors and told Dean not to tell Gabriel that it was her). He also made Gabriel take Saturdays off after he almost collapsed into the coffee maker.

It was looking up for the trio. Dr. Milton said she thinks the chemo is working, slowly killing off more cancerous cells. Castiel was still sick, but, seeming as though it wouldn't last too much longer, he thought he could live with that.

Dean usually took Castiel out on dates once or twice a week. It was never anything fancy. Sometimes it was something simple like hiking or driving around. Other times it was just going out for Dean's lunch break to some cheap diner. No matter what, it was always amazing to Castiel.

Today, however, was different.

The beginning of fall was Castiel's favorite time of year (besides Christmas, of course). He loved seeing the monotonous green leaves turn to vibrant oranges, yellows and reds. Driving through downtown, with all the trees planted for decoration, made everything look gorgeous.

Dean was driving with Castiel for another date. Castiel always wore his gray hoodie whenever he went outside. He didn't like how he looked bald.

"So," Castiel said, turning to Dean. "What's the plan for today?"

"It's a surprise," Dean said casually.

Castiel huffed as he turned back to the window.

"I'm going to assume fall is your favorite season?" Dean asked.

Castiel nodded. "I just love all the colors. I know that makes me sound like some teenage girl from a rom-com, but-" Castiel shrugged. "-I love it."

Dean smirked. "I actually think spring is my favorite season. Summer's way too hot. Winter's too cold. And fall is just a winter greeting."

Castiel chuckled softly.

A few minutes later, Dean pulled into a Walmart parking lot. "Dean, what are you doing? I thought we were on a date."

Dean pulled into a parking spot near the back and parked the car. "We are," He said as he turned off the engine.

Castiel was confused as they stepped out of the car and headed to the entrance. He didn't know what Dean had planned, but he was starting to get both suspicious and excited. It was a strange combination of emotions.

Once they were inside, Dean stopped him as he was about to grab a cart. "Okay, so I know this is kind of random, but I have a game." Castiel tilted his head, both out of interest and confusion. "The challenge is to buy each other an interesting outfit that we each have to wear the rest of the day. I have a budget of fifty dollars and a time limit of forty-five minutes. We'll meet at the changing rooms in the back." He glanced at his watch and set a timer. "Time starts...NOW!"

Dean took off running for the clothes, almost running into a little girl with a doll. Castiel actually thought his outfit through before he took off towards kitchen supplies.

Exactly forty-five minutes later, Castiel found Dean waiting with his outfit back by the dressing rooms. From what Castiel saw, he actually had a nice outfit planned. He saw a pair of blue jeans, a light blue t-shirt, and what looked like a dark green head scarf.

He looked down at the outfit he was carrying and chuckled to himself. He had a cheap pot for a hat, a bright red thong, a blue t-shirt that said 'I wuv hugs,' and an ugly floral skirt. He laughed harder.

Dean turned his way with a grin, but it faded almost instantly when he saw what Castiel was carrying. "Aww, hell no!" He shouted. "You can't just-"

"You only said it had to be fifty dollars and that I had to be back here on forty-five minutes," Castiel giggled. "So, I let my imagination run wild."

Dean grabbed the bright red thong off the top of the stack. "Really Cas? A fucking thong?"

"Yes, really. Now go try this on!" Castiel shoved the stack of clothing into Dean's arms. "I want to see what this looks like on you!"

Dean chuckled lightly. "You 're such an asshole."

"You're the one who decided to not specify rules." Castiel shrugged.

Dean came out of the changing room fifteen minutes later. He obviously debated coming out to show his boyfriend what he looked like in the outfit he picked. WHen Castiel saw him, he didn't hold back his laughter.

Dean's face was as red as the thong he was wearing. The skirt reached just above his ankles (Castiel didn't want the thong to show when they were outside). The blue shirt matched terribly and the pot on his head was just the best finishing touch.

Castiel was rolling on the ground, tears in his eyes and arms around his stomach, laughing. "Okay, fucker. Now it's your turn," Dean said, but without any bite.

Castiel stood up, still laughing, and took his clothes to the changing room.

The clothes that Dean chose for him fit amazingly on him. The jeans hugged him in all his best places and the shirt was loose, but not too big. The headscarf didn't really match the rest of the outfit, but it was beautiful. The headscarf was silk and already pre-tied. It felt smooth on his head.

Castiel sauntered out, knowing he looked good in the outfit Dean chose for him. Dean changed out of the outfit for now, since they still had to buy it, but was staring daggers at it. When he caught a glimpse of Castiel, bit eyes widened slightly and he stood up, meeting Castiel just outside the changing room.

"Wow," He said breathlessly. "You look gorgeous."

Castiel blushed slightly. "Thank you, Dean."

Dean leaned in and wrapped his hand around the base of Castiel's neck and kissed him gently. Castiel ran his hands up and down Dean's back and Dean brought his other hand up to cup Castiel's cheek.

Dean pulled away, but kept his hands on Castiel's face. "I figured that, you know, since you don't like the way you look bald, I would get you a headscarf so you don't look like such a creep."

"There are hoods on hoodies for a reason, Dean," Castiel said.

"I know, but-" He gestured to Castiel's headscarf. "-you look so much better in this. It hides your face less."

Castiel grinned and leaned back up to kiss Dean again. "Thank you. This was a pretty good date idea."

"For you maybe," Dean said. "I still have to wear that fucking skirt and thong for the rest of the day."

An old man an aisle over gave them a weird look.

"Kay then. Let's pay for this and change back into them." Castiel gave Dean a sly look.

"Ugh, fuck me," Dean mumbled.

"Maybe later," Castiel whispered in his ear.