Shit. He was really going to do it. Holy shit. Dean's nerves kept him silent on the way home from Cassie's hotel room. As they approached their apartment door, Dean heard Charlie crying. Quickly, he and Cas walked in.

"What's going on?" Dean asked. Charlie had her face buried in Dorothy's shoulder.

Dorothy shook her head at Dean, "Don't worry. We just finished watching Les Mis. You know how she is."

Charlie wailed, "Why can't they just live? Just one time!" Dean turned towards Cas, who was still looking at Charlie in utter confusion.

"Do you want to go out?" Dean asked.

Cas' eyebrows knit together, "But Dean, we just got back from being out."

"No, Cas," Dean said, grinning, "I mean, do you want to go out on a date?"

Cas' eyes widened, and Dean just about drowned in all that blue. He had to do it. It had to be today. Maybe not around Charlie being overly emotional about a movie, but it had to happen.

Cas smiled, "Are you asking me out?"

Dean gave Cas an exasperated look.

Cas laughed, "Okay, where do you want to go?"

"I have an idea," Dean said.

They walked out the door, Dean leading the way.

"Where are we going?" Cas asked.

Dean smiled at Cas, "It's a surprise."

Dean started second guessing his plan. But it needed to happen. He had to do it. Still, he wanted a little insurance.

"Cas," Dean asked, "If we broke up, what would you do?"

Cas stopped walking. "Why?" he asked, suspiciously.

Dean said, "Just curious." Cas nodded, his eyes never leaving Dean's face, and continued walking where Dean was leading.

"I don't know," Cas said, "I'd be very upset. I'd probably cry, maybe take a long walk to have some space. I don't know." That wasn't quite what Dean was getting at.

"Where would you live?" he asked.

Cas sighed, "Would you really kick me out again?"

Dean shook his head, "Probably not. But would you want to live with me if we broke up?"

Cas stopped walking again. "Dean, you are really starting to worry me," he said.

Dean smiled, "No, it's not that. Don't worry. Just asking questions."

Dean's heart raced. This could work. This could be okay. They kept walking for a while in silence, but it was comfortable. Dean reached for Cas' hand when they came to a red light.

"Jesus, Cas, your hands are freezing," he said.

Cas shrugged, "I'm used to it."

Dean took Cas' hands in his and breathed warm air on them.

Cas smiled at Dean. "You don't have to do that," he said.

The light turned green, and they crossed the street. Dean pulled his gloves out of his pockets.

"Here," he said, "Take these."

Cas shook his head, "You really don't have to. Your hands will get cold."

"They've been fine so far. Seriously, take them," Dean said.

Cas reluctantly pulled the gloves on and held Dean's hand. "Thank you," he said.

Dean grinned and said, "We're almost there."

Cas looked around and said, "We're not really close to any...Dean, are we-?"

Dean nodded.

As they rounded the corner, Dean watched Cas' eyes widen and a smile spread across his lips.

"Figured our first real date could be where our first not-a-date was," Dean said quietly.

Cas turned and kissed him softly.

"I don't know what to say," Cas murmured.

Dean led Cas across the street to the two towers of Millennium Park. The towers, while still showing faces, were not covered in falling water like they were in the early winter when Dean and Cas had first gone.

Dean asked, "You want some hot chocolate?"

Cas nodded. They walked over by the skating rink to the vendors. Dean ordered the hot chocolate and handed one to Cas. Dean leaned against the rail encircling the rink. Everyone seemed to have so much fun skating. Dean sipped his hot chocolate.

"What about sex?" Dean asked suddenly.

Cas almost dropped his cocoa onto the ice.

"What?" Cas asked.

Dean felt the sudden rush of blood to his cheeks warming his face against the cold air.

"I mean, if we have sex, how would we...?" Dean tried.

Cas kissed him and smiled warmly, "We'd do whatever you're comfortable with."

"But what would you be comfortable with?" Dean asked.

Cas shrugged, "I don't know. I've never done anything. We'll figure it out when we need to. Don't worry."

"What if we needed to figure it out now?"

"Dean, you're not ready for sex. You said so not all that long ago."

"What if I am ready?"

Cas grinned, "Are you proposing we have sex in the cold in the middle of Millennium Park?"

Dean shook his head, "No, I just-"

Cas said softly, "Don't worry so much. It'll be fine." For whatever reason, that did help Dean calm down a bit. He still had to do it, though. He needed to. But it didn't seem like the right time.

"What if we broke up?" Dean asked.

Cas sighed, "We already talked about-"

"No, I mean what if we broke up after we had sex? I'd be your first and if we broke up, I don't know-" Dean said.

Cas stopped him, "Dean, if you break up with me, it will hurt. Period. End of story. That's how breaking up is. If you have my virginity, it might hurt a little worse, granted, but I don't care. Whatever we share in the time we have together is worth anything pain that comes up later."

Dean looked back at the people on the ice. Some were more experienced than others. Some were wiping out every few steps while others did tricks in the center of the rink.

"You say that now," Dean said.

Cas looked at him. "Is something wrong, Dean?" he asked.

Dean shook his head, but his heart was about to burst out of his chest.

Cas held Dean's gaze and grabbed his hand, "You are a terrible liar. What's going on?"

Dean cleared his throat, running his hand over the back of his neck. "Nothing," he said, "Really."

Cas gave him a very concerned look.

"C'mon," Dean said. Cas followed him, despite his apparent worry.

He didn't want to worry Cas. That hadn't been the intention. Dean really needed to just get it out there before anything got any worse. Even if he didn't want to, even if it scared him, this had to happen. They walked past the Bean over to the band shell. Dean could just see the frozen shores of Lake Michigan from where they stood.

"I need to tell you something," Dean said, looking out at the snowy beach. No, he had to do this face to face. He had to. Dean forced himself to look at Cas. There was so much concern in his boyfriend's face, but there was no hiding the amount of love there. It made Dean feel amazing to have that kind of affection aimed at him.

"I'm sorry if I made you worry, Cas," Dean said, "I promise everything's fine."

Cas sat with Dean on one of the metal benches near the band shell. He seemed a bit more at ease but not enough.

Dean said quickly, "I was only asking about if we broke up, because I need to know that if, for whatever reason, we do split up, that you'll be okay. I need to know that it won't be like when I kicked you out. I need to know you'll have a place, and you'll still eat meals, and you'll be safe. I need to know you'll be alright."

Cas stared at him but finally asked, "What's this about?"

"We're family, Cas," Dean said, "I need you. And if we ever broke up, that would still be true. We'd still be family. I'll always need you."

Slowly, Cas wrapped his arms around Dean and hugged him tightly.

"I know. I need you, too," Cas said quietly.

Dean hugged his boyfriend back and buried his face in Cas' jacket. It was so warm, Dean was reluctant to move from that spot.

"Do you want to go out to dinner?" Dean asked.

Cas grinned, "Was that really all you wanted to tell me?"

"Yeah," Dean lied.

Cas stood up and pulled Dean up with him, "Then you may take me out to dinner if you'd like."

Dean smiled, "If I didn't want to, I wouldn't have asked."

"If I didn't want to, I wouldn't have answered you," Cas said.

"Well, there's this pizza place," Dean said, "I can't remember its name, but I know where it's at."

Cas said quickly, "Sounds good. Lead the way."

They walked north for a bit, neither saying much of anything.

When they were about a block away, Cas asked, "Was it really necessary to give me a heart attack back there?"

"What?" Dean asked.

Cas sighed, "I was really starting to think you were going to break up with me."

Dean stopped and hugged Cas gently. "I'm sorry," he said. He released Cas and looked him in the eye, "I didn't mean to freak you out, I swear."

Cas smiled. "So, where's this pizza place?" he asked.

Dean replied, "Just a little further. It's got the best pizza ever. You're going to love it. It's not just pizza, it's like a pizza pot pie. And they've got this amazing bread-"

"Dean, I'm already hungry enough," Cas said.

Dean grinned, "Sorry."

When they arrived at the restaurant, Dean spotted a sign on the door.

"Shit," he said.

Cas asked, "What?" Dean pointed to the sign.

"Cash only," Dean said, "I don't carry cash."

"Maybe they have an ATM?" Cas suggested. That was a good point. With a cash rule like that, they should definitely have an ATM. Dean led the way inside.

It was darker than he remembered. He still had no idea what this place was called. It was sort of a hole in the wall entrance, and there didn't seem to be any signs inside. A server came up to seat them.

"Two?" she asked.

Dean said, "First, do you have an ATM?"

She looked at her menus awkwardly, "We do, but it's out of order. I'm sorry."

Dean sighed. This had been a great idea. Cas gave Dean a small smile.

"Sorry," Dean said to the server. They walked back outside. It was starting to get very dark in the city.

"Where to now?" Cas asked.

"I don't know," Dean said, "I'm sorry, Cas. This was supposed to go a lot better."

Cas replied, "It's fine. I just need food. We could stop at a McDonald's, and this would still be the best date I've ever been on."

"I'll make it up to you," Dean said.

Cas sighed, "Seriously, Dean. Is there a McDonald's nearby?"

Dean grinned. "Yeah," he said, "Up the block."

Cas led the way, fueled by apparent starvation. The determined way Cas was walking just made Dean adore him more. He was so ridiculously cute, and he wasn't even trying.

They wound up grabbing some chicken nuggets to go and headed back to the apartment. By the time they got there, Dean missed his Impala with a violent passion, and he could barely feel his toes due to the cold.

They went inside and found Charlie asleep on Dorothy's lap. Dorothy was reading something, only looking up to greet them with a smile.

"We'll take this to our room," Dean said softly.

Dorothy mouthed a quick 'thanks' and tucked a strand of Charlie's hair behind her ear.

Dean approached Cas, who had just jumped onto the bed with his chicken nuggets, and started feeling nervous all over again. But c'mon. This was Cas. It would be okay. If they broke up, Cas would be fine. If they stayed together, that'd be great. They would take care of each other no matter what. Dean swallowed his fear and sat on the bed with his boyfriend. He didn't want to freak out Cas again. He didn't want to shock him while he was eating either. So, he waited. He munched on his own dinner for a bit, but his stomach was too antsy to bother with much food.

Soon, Cas finished eating and looked at Dean.

"Are you okay?" Cas asked, "You look...Dean, what's going on?"

"What if I didn't feel about you the way you think I do?" he asked. As the words came out of his mouth, he wanted to kick himself in the face. Cas turned about two shades whiter.

"God, no. That's not what I mean. Shit," Dean stammered. Nut up or shut up, Winchester. Dean took a deep breath.

He looked Cas in the eye and caught him in a full kiss. He wrapped his arms around his boyfriend and kissed him again. And again. When he stopped, they were both panting. Dean pressed their foreheads together as they caught their breath.

Cas said between breaths, "Dean, what-?"

"I love you," Dean said softly.

Cas backed up from Dean quickly and fixed him with a warm, blue stare.

"Are you serious?" Cas asked.

Dean gave him a confused look.

"That's what this was all about? You were trying to tell me you love me?" Cas asked.

Dean nodded.

"You made me think that you-But it was just-," Cas stammered, flustered.

He paused and said, "I love you, too, Dean."

Dean kissed Cas as his heart hammered in his chest. He was so glad Cas wasn't mad at him for being a basket case. It was such a relief.

Cas pulled Dean on top of him and kissed him within an inch of his life.