Chuck was an early bird by force, not by choice. It had occurred to him long ago that the only safe time he could ever really get to himself was around 4-6 a.m., when all of his hellspawns were still asleep and he didn't yet have any responsibilities. So it was at around this time that Chuck sat at his kitchen counter, sitting coffee and thinking about, of all things, the Winchester boys.

For starters, he found the coincidence of their names slightly alarming, but the universe was strange like that sometimes. He was more concerned, though, with how smitten Castiel and Gabriel were with the two brothers. Both of them lit up at any prospect of seeing them, and the boys were basically all they talked about lately.

It wasn't that Chuck minded that his sons were dating. Far from that, actually. He low key shipped his kids and their dates, although he hadn't gotten too interested in them since he'd had his heart broken at the great 6th grade break up between Anna and a boy named Connor.

Damn, he missed Connor. 

But thankfully, Lucifer and now Gabe and Cassie gave him plenty of ships to think about. The thing that was worrying Chuck was that he had never met the Winchester boys before, and as a good Dad, that meant that Chuck was skeptical of how wonderful they actually were.

It wasn't like he hated them- well, not yet, at least. He was just afraid that the boys weren't all Cassie and Gabriel were making them out to be, and he didn't want to see them get their hearts broken. ESPECIALLY Cas. Gabriel had been through bad break ups before, and he always came out okay, but Cassie? He had barely admitted to having a crush before this, and now he was dating Dean. The poor kid had fallen hard and fast for the eldest Winchester, and Chuck was wary of that. He had to protect his kids, especially when they were in a situation they didn't have experience in, like love.

And Chuck knew better than most how much love could fucking sting.

But he could also have no reason to be suspicious of the Winchesters. They could be just as perfect as his sons insisted. There was only one way for him to find out, after all.

So once his angels woke up for breakfast, he immediately announced his plan.

"So," He started casually, glancing between Cas and Gabriel. "I had an idea."

"Oh no," Gabriel whined. Chuck's ideas were never good for them.

"I think we should have the Winchesters over for dinner," He insisted. "You boys talk about them so much that I think it's about time I finally met them."

"You want us to bring Sam and Dean over for dinner?" Cas echoed, his eyes wide.

"And their parents too, why not? You said they were new in town, I'm sure their folks would appreciate it. How about on Friday?"

"Hell no!" Gabriel yelped. "I'm not bringing my Sammoose over here so you can all interrogate him!" Cas nodded in agreement.

"And it seems kinda early in the dating process for the whole 'meet your parents' thing," He mumbled.

"It's not an interrogation!" Chuck insisted. "It's just a dinner so I can get to know them, and they can get to know us."

"If it's not an interrogation then why are you singling out the Winchesters?" Gabriel asked. Chuck thought for a moment. 

"Fair enough- LUCI!" Lucifer ascended from the depth of hell and raised an eyebrow. "Invite Chloe over to dinner on Friday. I want to have a nice meal with all my kid's significant others." Satan made a face.

"You're not gonna interrogate her, are you?" He asked.

"It's NOT AN INTERROGATION!" Chuck yelled. "I just want to know what kind of people my kids are dating, is that so much to ask?"

"You've met Chloe a thousand times."

"Yes, I know, and I love her, and if you ever give her a reason to break up with you, I will disown you as my child."

"So my fate in this family relies on my ability to hold my girlfriend hostage, got it." 

"No, no, he's got a point," Cas agreed. "If you don't marry Chloe, it'll be a crime against humanity."

"And what if she doesn't wanna marry me, dumbass, what then?"

"Then we'll all cry for eternity." Gabriel and Chuck nodded in agreement and Satan groaned.

"Why must you all approve of my love life," He grumbled, heading back downstairs.

"Don't forget to-" Chuck started.

"SHE'LL BE THERE!" Chuck turned back to his sons, triumphant.

"See? Chloe will be there. Now your boyfriends aren't being singled out." Cas went bright red and Gabriel's eyes widened.

"B-boyfriend?" Cas stammered. "Dean's NOT my boyfriend. I mean, I'd like him to- I mean- we haven't really- uh-"

"It's not official yet," Gabriel explained. "For either of us."

"Mhmm," Chuck looked skeptical. "Well, invite them and their parents over to dinner anyways. I wanna meet them."

"Okaaaay," Cas and Gabriel reluctantly agreed.