Chapter 22

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Jody Mills is the mom that Dean Winchester never had.

When Dean went viral off a video of him singing karaoke at a bar on his 21st birthday, Jody invited him on her talk show within a week. She was the only person to reach out to him — even Ellen DeGeneres didn't seem to think his shitty rendition of "I'm Too Sexy" warranted any screen time.

Jody gave him the chance to prove that, while his drunk karaoke is questionable, he can put on a great show when he's sober. Obviously, he had to sing "I'm Too Sexy" again, but he also sang an acoustic rendering of Lynyrd Skynyrd's "Simple Man," which basically launched him straight into stardom. When someone hands you a career like that, you don't forget them.

So that's why Jody's talk show is the first place he goes to promote his new single, "Going Well." The whole joke, not just he could admit it to anyone outside of the operation, is that things stopped going well immediately after the single was announced. It's the irony of the situation that's supposed to sell it. He can't even imagine how many "Things don't really seem to be going well for him" viral tweets he's going to see soon once he confirms the breakup.

But let's not get ahead of ourselves here. We still have a whole talk show to listen to.

The first thing he does is perform the new song. It's the song's first performance, so it has to be big, and he'd like to think he succeeded on that front. Plus, given that the song hasn't been released yet but will be by the time this airs, it's good to make sure that the audience knows the song he's talking about.

And then it's time for the real show. He's reintroduced after what will be a commercial break, and he walks out with a smile on his face and waves at the audience. He gives Jody a hug before sitting down next to her, their bodies angled towards the cameras.

"Well, congratulations on the new single!" Jody says, and her excitement for him seems genuine, which is what he appreciates about this show as opposed to ones like The Graham Norton Show, where Graham genuinely couldn't care less about the guests and has publicly admitted as much. 

"Oh, thank you," Dean says with a warm smile. "I've been really looking forward to this song coming out since I decided this was the lead, and I can't believe it's already here."

"I'll bet," she says. "Why'd you pick this song as the lead single, anyway?"

Dean has to admit, he admires how she did that. It was subtle, a casual flow into exactly what he wants to — or, technically, his team wants him to — discuss today.

But he can't make it obvious what he's trying to get to, either, so he has to beat around the bush, too.

"It was actually one of the first songs I wrote for the album," Dean says. "I'd just started my last tour and I was looking out at that stadium full of people and I was like damn, things are just really going well for me right now. So, obviously, I turned that into a song, and I kinda turned that song into a whole album. It was just a whole album of happy, and what better way to set that up than the song that started it all?"

The audience cheers, and Dean beams. Oh, aren't they adorable? He can't wait to see how stupid they're going to feel when they realize he was speaking in past tense for a reason.

"It was actually going to be the title track, but I decided to change that a few days ago," Dean adds. Obviously, he's not dumb enough to name a whole album Going Well, but it's the story he's going with anyway.

"Can I ask what the new title is?" Jody asks.

"You can ask all you want, but I'm contractually obligated to not give you a straight answer," Dean replies, and the audience laughs.

"Ah, dang," Jody says as if she didn't already know that. "Well, it's still a fantastic song. You've outdone yourself once again."

"Thank you!"

"Now, obviously, I have to ask," Jody says. "Has Jo heard the song yet? How'd she feel about that little shoutout?"

The audience cheers at the mention of her name, but, when they see Dean's smile falter, they shut up immediately.

"Uh, yeah, she did." He looks down at his lap, fiddling with his thumbs. "But we're, um..." He lifts his gaze back to Jody's timidly. "She's not really in my life anymore."

There's a loud "Awww!" from the audience.

"Oh, no, I'm so sorry," Jody says quickly. "I didn't realize..."

"No, it's okay," Dean assures her, but he makes sure that it's clear to everyone listening that he's heartbroken. "It just... wasn't working out. Too many outside factors." It sounds vague now, but he knows people will put two and two together soon and realize he's talking about Castiel, probably before he even mentions "someone" stabbing him in the back later on in his promotion cycle.

"Still, I'm so sorry to hear that," Jody says. "Do, uh... do you want to tell us about your new song?"

And, just like that, the interview is back on track. It's a lot easier to reroute interviews like that when the interviewer knows the ins and outs of the subject — particularly, the fact that their relationship was fake — and Jody knows everything.

In the wise words of the Staples button, "That was easy!"

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