"I mean it, Gabriel." Castiel sighed heavily. "He's just a friend"

"Oh sure, Cassy, sure" Castiel pressed the bridge of his nose between his thumb and forefinger, he could hear the wink that Gabriel shot Anna through the phone line as she scolded him.

"Gabe, even if he was, you can't go scaring him off!"

"Ugh, fine. But you owe me!" whined Gabriel.

"I owe you for not being a dick?" Cas pushed, trying to make sure that Anna could hear and would keep Gabriel in check. He felt bad playing her emotions like that, he knew she was concerned he'd disappear like he did when their Father died; this was the first time they would be getting together since. Still, he didn't want what he had already made an awkward situation any worse with Gabriels teasing. He hoped that Dean could hold his own, but with the insinuation that they were an 'item' he didn't know. Dean had never seemed homophobic, but Castiel wanted Dean to like him, at least for the sake of friendship, and even if Dean could take a little teasing, he didn't know if anyone could take how relentless Gabriel could be when he had a few glasses of wine in him.

"Cas?" Anna asked, seeing if he was still on the line

"Yeah" The man was pulled from his thoughts.

"Okay, good. Listen, I'll make Gabriel behave. It's good you're bringing somone. I know, I know just a friend and all, but it's good you have a friend other than Meg. Not that Meg isn't great, but you know what I mean? Someone other than your ex-wife." Anna paused.
He felt bad that Anna was so nervous about Christmas. He was going to come, and there really wasn't much that could change that. He was used to his siblings, and last time was different. Even if Gabriel tanuted Dean into a full-blown fist fight, he'd still come around. His siblings weren't awful, and they really did care; he had to hold onto that.

"Anna, it's going to be fine. I am really excited to see you, and the kids." He said softly, trying to ease the worry he had created "Dean can handle it, he's a grown man even if Gabriel is still a child, and I know Gabriel doesn't mean it to be hurtful. I'll give Dean the heads up. I love you."
Anna sighed with relief "I love you too, Castiel"

Castiel took two suitcases, his and Ishmael's hastily packed, downstairs to the parking deck where his car spent most of its time. Cas sometimes wondered why he even had one.

Gabriel moved to Ohio shortly after Abraham died. With nothing keeping him in New York, he quickly left. Castiel honestly had no idea where Balthazar and Uriel were living with their booming plastics business, which he resolved to learn more about this year, at least the name of the company. Anna had gotten engaged about 3 months ago, it upset Castiel to think about how he was not there for that, that he didn't know his name until last week, she didn't have Sarai and Abraham there for her, and she was the closest to them both, and Castiel had let her down; he resolved to quit letting so many people down.

Castiel pulled out of the parking deck, and slipped on his bluetooth., calling Megra first.

"Hey, Cas!"

"Meg, I'll be there shortly. I-uh... I have to pick someone up first, then we'll pick up Ishmael."

"Oh?"

"That's not a problem, is it? I can pick up Ishmael first if you-"

"No, no you're fine! I don't want to pry, but you know I'm intrigued by your mystery man."

"Who said it was a man?"

"Now I'm hurt!"

Castiel groaned

"Yes, it's a man, but it's not like that"

"Sure"

"Seriously"

"Alright, alright!"

"You've met him, anyway."

"Oooh!" Cas heard Ishmael squalling for him in the background "Okay, well we'll see you soon!"

"Okay, Love you"

"Love you too, bye"

He then called Dean

"What's the plan?" Dean sounded well caffeinated

"I'm coming to pick you up now, then we're going to get Ishmael. Are you ready?"

"I've been ready for two hours, what the hell have you been doing?"

"You've never packed for a toddler"

"What could that kid need?"

"Anyway, I'll be there in five" Cas hung up and anxiety washed over him.
He wondered if Dean was a family man, if maybe one of them wanted kids, and the other didn't. With context Castiel assumed that Dean was the one who didn't want them, saying how he "just couldn't". He thought about all the possibilites he could in about two minutes before he wondered if Dean would want him less because of Ishmael. Nobody really likes someone with baggage, and a kid counts as baggage. Castiel shook his head, it didn't matter what the hell Dean thought, first of all Dean didn't want him and second Ishmael would always be priority.
Castiel really did need more time to figure his life out, he didn't realize that he hadn't really established his priorities, or even thought about dating anyone until now.

Castiel was barely in the driveway of Dean's condo when Dean came out, baggage in hand and clearly 100% ready to go. He popped the trunk and Dean put his things in, and hopped into the front seat.

Castiel stared at him for a moment.

"What?!" Dean beamed warming his mitten-ed hands over the vents. "Are we going, or what?"

"I.. yeah." Cas pulled out of the driveway and headed towards Megra's.

Dean was clearly excited, and caffeinated. Dean pulled his iPhone out and hooked it to Castiel's built in jack.

"Only good thing about these new cars" Dean mumbled as he clicked into a playlist "Gotta have a road-trip soundtrack!"

"I hardly think this is a road-trip"

"The hell it isn't" Dean turned on Wheel in The Sky by Journey "I haven't had a roadtrip in years, I'm just glad not to be on a plane."

The rest of the ride was mostly Dean jamming to 80's hair music, for as long as it took for them to get to Megra's, it was about one song

.
They pulled up to Ishmael pressing his face to the front window behind the couch, squaling and smacking the glass when he saw Castiel. Cas turned to tell Dean he'd be back, and Dean was already out of the car walking ahead to meg standing in the doorway. Cas stood by the car for a moment watching Dean introduce himself to Meg with a handshake, Ishmael clung to Meg's leg, looking up apprehensively at the man before him. Dean knelt down and Cas couldn't hear what he was saying, he walked to the door and greeted Meg with a hug and a kiss on the cheek, she looked down at Dean and just smiled at Cas.

"shut up" Cas mouthed silently.

Ishmael looked away from Dean and beamed to see his Dad. He held his arms up saying "Go! Go!" Cas gave him a kiss and set him back down "Just a minute, buddy. i have to grab your bag and we can't leave without your jacket"

"Go! Ishmael bounded to the livingroom where his boots and coat lay sprawled next to pieces of a hot wheels track
"He had those on a minute ago" Meg chuckled.

Dean was in the livingroom asking Ishmael all sorts of questions, and the boy ate it up. It a matter of minutes Dean was helping him into his coat and boots, promising they could take the two hot wheels cars they had been playing with.

Cas followed Meg upstairs to grab a few extra things for Ishmael before they left.
"Well well." Meg smiled

"Well, what."

"Is he?"

"Gay? No. Not that I know of."

"Would you be interested if he was?"

"Do we have to do this now? Anyway it's kind of awkward, don't you think?" Castiel wanted nothing to do with this conversation.

"No. I want you happy, but I'll let it go. For now." She rubbed her hand along his shoulder and grabbed the bag for Ishmael. "Give everyone my love, okay?"

"Of course" Castiel kissed her on the cheek again and they walked down stairs.

Dean was wearing Ishmael's hat on the top of his head, the boy was in his arms reaching for the hat. They were both laughing as Dean waved his head around to keep the hat from the boy's hands.

It was then that Castiel and Meg both knew that Cas was a goner.