It had been a very, very long time since Chuck had gone out for a night with friends and no kids. He couldn't honestly remember the last time he had, although it had probably been before he and Naomi had gotten married.

But there was no real reason why he couldn't go out, especially now, since his kids were old enough to be trusted to stay home by themselves. Well, trusted wasn't the right word- they were old enough to survive if left home alone for a few hours. Well-

Well Chloe was at the house, so she could look after everyone and make sure nobody died. There, that could put Chuck at ease.

Mary Winchester, of all people, had asked him to hang out. Apparently Ellen Harvelle wasn't happy that her old friend had been in town for so long without them properly going out and drinking together, so that's where it had started, and Ellen had invited Bobby, Mary had invited Chuck, and Chuck always brought Amara to situations where he didn't know what to expect, so thus formed their little drinking group.

So while Chuck's kids stayed home doing god knows what (Currently Lucifer and Chloe were answering letters from the Satanic Church, Michael was doing homework, Balthazar was using Hannah as a living mannequin while he altered a dress, Anna was at a party, and Charlie, Cas, Gabriel, Jo, and Sam and Dean were over at the Winchester's house having a giant, brutal Mario Kart tournament), Chuck and Amara headed out to Rocky's Bar.

"Chuck! Over here!" Mary called as they wandered in, the rest of the crew already gathered and one drink in.

"Hi all," Chuck offered.

"Great, everyone's here," Ellen insisted, waving a waiter over. "Now we can do shots."

"ELLEN!" Mary objected.

"Ooooohhhh YES," Amara agreed. "I already love you."

"Some of us have to work tomorrow," Bobby reminded her.

"Please, Bobby, like you've never gone to work with a hangover before," Ellen said, swatting at him. "I remember, our senior year you got so plastered right before Midterms that you decided to just keep drinking in order to put off the hangover, and you ended up ripping your exam in half and swearing at the teacher." 

"I really should stop talking to people who know all my embarrassing stories," Bobby muttered. He turned to Chuck and Amara. "But I haven't met you two yet, what's your story?" Chuck held out a hand and Bobby shook it.

"Chuck Novak. Writer. Generally crazy person. This is my sister Amara, who has more braincells and less sanity than me."

"You got that right," Amara said.

"Novak?" Bobby echoed. "Wait, are you Castiel's father?"

"The one and only." Chuck said proudly.

"Dean never shuts up about your boy," Mary nodded.

"You can say that again," She said. "Every day Sam and Dean come home from school and all I hear is what the Novak kids are up to. I'm sure they exaggerate some of it, but still."

"The scary thing is I doubt they're exaggerating," Chuck said. "If you knew half the things my kids have done over the years, you'd put your own up for adoption just in case."

"Your kids are the reason I'm never getting married," Amara insisted.

"I don't blame you."

"How many kids do you have in that house of yours, Chuck?" Ellen asked. "Cause I'm pretty sure my daughter is dating one of them."

"Eight teenagers- who's your daughter with?"

"Charlie?"

"Yep, she's one of mine!" Chuck admitted. "Well, actually she's the only one that isn't my kid, but since she and Cas were so close, I adopted her after her parents died, so I'm technically legally responsible for her."

"She's a sweet kid. It's gotta be hard raising so many kids on your own, though."

"I can't even imagine," Mary went on. "I'm having a hard enough time with two, but EIGHT? How are you even still standing?"

"Two reasons." Chuck explained, picking up a shot. "One, I have help." Amara waved. "And two," He clinked his shot glass against Amara's. "We drink." They killed the shots and Ellen and Bobby started laughing.

"It almost gets worse the older they get," Mary said. "When Sam and Dean were little, they were hyper and loud, of course, but they were easy to manage. Now Dean just gets in his car and drives to who knows where whenever he wants, and I have no idea how to rein either of them in."

"You lose more and more control the older they get," Ellen agreed. "I think you just have to accept it and see it as them becoming independent. There's not much to can do to control where they're going, who they're hanging out with, who they're screwing, etc. You just try to make sure they're prepared, and be there when they need you."

"Oh, don't get me started on who they're screwing," Mary scoffed. "The Talk was the single most embarrassing and miserable moment in my entire career as a parent."

 "I'll bet," Chuck said. "That's why I never did it."

"Wait, you never told your kids-"

"Nope."

"But-"

"Mary, we live in a modern world. Anything I'm gonna tell them they already learned two years ago from TV or the internet. It just seemed pointless to do, and my kids haven't had any problems so far."

"Yeah, but there's a lot TV leaves out. They don't talk about things like birth control or-"

"Oh, I handled that," Amara said. "I made damn sure all those kids know about that stuff. I hand out condoms like candy to most of them."

"Wait you do?" Chuck's eyes widened. 

"Hell yeah. You never used them and look where that got you."

"It got me a wonderful family."

"It got you SEVEN CHILDREN."

"And I regret nothing."

"Of course not, you're stupid."

******

Several rounds later, Chuck felt like he had been friends with Bobby, Mary, and Ellen for years, and they had already made plans to do this every week.

"So," Chuck started, pointing at Bobby and Ellen. "What's the deal with you two?"

"What do you mean?" Bobby asked.

"Cause I happen to know that there is a plot among the children to make sure you guys end up dating, so where's that coming from?" Bobby choked on his drink and Ellen laughed.

"It's a long story," She said. "We went to high school together, were best friends with Mary and John, of course," Mary offered her a tight smile at the mention of John. "Then they started dating, so suddenly Bobby and I were spending a lot more time together. One thing led to another and then we started dating."

"But high school romances aren't always perfect," Bobby said.

"No they weren't. Our relationship was like a forest fire, it just kinda blew up on us, so we broke up shortly after graduation. I moved with a friend to Sioux Falls for awhile and met Jo's father, Bill. We moved back here after we got married cause I missed the old place, started the diner, had Jo, and then..." She paused. "And then Bill wasn't in the picture anymore."

"I never left the town," Bobby said. "Just graduated and started up my shop outside the house where I grew up. Dated around for a few years, but nothing really stuck, so here we are." He smiled. "Part of me wonders what would've happened if we had just stayed together."

"Certainly be a different life," Ellen whispered. She and Bobby stared at each other for a moment and Amara leaned toward Chuck.

"How the hell do we Parent Trap these bitches?" She hissed.

"I don't know, but I'm joining the kids' side," Chuck whispered back.

"Well maybe you two should give it another try," Mary suggested, snapping Ellen and Bobby out of their trance. "I mean, everyone always said John and I were perfect for each other, and that was a trainwreck. Maybe having the wisdom to break up in high school and wait til you were adults was the better move and it'll pay off."

"I don't know," Ellen sighed. "I haven't seriously tried dating in years."

"What have you got to lose?" Bobby asked. "I've got nothing."

"Well," Ellen smiled softly. "Maybe you've got a point."