[Warning: The following contains spoilers from Monday's episode of Supernatural. Read at your own risk]
Monday's episode, titled "Destiny's Child," began with Sam (Jared Padalecki) and Dean (Jensen Ackles) alerted to a strange noise coming from the library. They arrived to find a pale green Fiat carrying their pretentious doppelgängers, expensive loafers and all. But before the Winchesters could get at why their look-alikes suddenly dropped in, the doppelgängers vanished through a rift.
After checking in with Cas about what just happened, the brothers were interrupted by Billie (Lisa Berry), who informed the gang that the alternate Winchesters were running from Chuck (Rob Benedict), who's been destroying his other worlds one by one. She went on to explain that Jack eating angel hearts was just the first step in her plan to defeat God. It was time to move on to phase two and a more spiritual quest, which entailed finding a powerful object called the Occultum. Jack, who strolled in eating a peanut butter sandwich, seemed ready, but the Winchesters weren't exactly sure about this plan. After all, Billie didn't provide details about how exactly they'd beat Chuck.
As the brothers researched the Occultum, Dean continued to question Billie's plan. Jack was supposed to kill Chuck, which would then leave Amara (Emily Swallow) alive and the universe imbalanced, which would then end all existence. To counteract that, Dean suggested that Jack also kill Amara to solve their potential dilemma. It works in theory, save for one giant hole: Who would take over after Chuck? Jack?
But there was no time to delve further into Dean's theory since they still had work to do. On a tip from Cas, they hit up Jo (Danneel Ackles), who was wrapping up her latest scam, about the Occultum's location. Illustrated through flashbacks, Jo revealed that she was approached years ago by Ruby (Genevieve Padalecki) about a buyer who would purchase the extremely powerful object for millions. Before Ruby could lock in the deal, however, she was killed by Sam and Dean, so now the Occultum is in Hell.
Elsewhere, Jack indulged himself with a feast of fried chicken, pizza, and hot dogs. But those delicious foods weren't enough to make him forget that nagging feeling of emptiness after burning off his soul. In a heart-to-heart with Cas, Jack revealed that he understood feelings like joy and sadness, but he no longer felt them in the same way he did before he lost his soul. He also noticed that things have changed with the Winchesters, especially Dean, after what he did to Mary (Samantha Smith), and wondered if the elder Winchester would ever forgive him. Cas, explaining that Dean feels things more acutely than anyone he's ever known, didn't have an answer for when that might happen.
As Sam and Dean prepped for their trip to hell to search for the Occultum, they ran into a new problem. The alternate Winchesters were trapped between dimensions, an issue that would have to be addressed at another time because they needed to find Ruby's special object. (Raise your hand if you choked when Cas referred to her as "the demon [Sam was] sexually intimate with.") Instead, Sam and Dean made their way to the underworld, where they were greeted by a demon who agreed to take them to Rowena (Ruth Connell), who now sat on hell's throne. Unfortunately, that turned out to be a trap, and the Winchesters were ambushed on Jo's orders. Yep, the fiery-haired angel had set them up.
Back at the bunker, Cas rightfully remained suspicious of Jo and decided to ask Ruby in the Big Empty about the Occultum's location. In order to get there, he needed Jack to draw his life force into a flash, which would kill him temporarily. If Jack somehow messed this up, though, Cas would be lost forever. It was an especially tall order for the young Nephilim given that he also needed to keep watch over the spell that sent Sam and Dean to hell. No pressure!
In the Big Empty, Cas called out to Ruby, but instead of the deceased demon, he got Meg (Rachel Miner). Actually, it was the Empty in the form of Cas' former flame. Not one to be messed with, Cas reminded the Empty that he was there on Death's authority, so it was probably a good idea to grant his request to see Ruby. Reluctantly, the Empty caved and Ruby was awakened.
With no time to waste, Cas immediately inquired about the Occultum, which Jo claimed was in hell. After asking about Sam, the "big lug" she admitted to really liking, Ruby set the story straight. Jo was the one who had called up Ruby when she realized they were on the brink of an apocalypse with Lucifer and Michael butting heads. Jo wanted to work together ahead of the new world order and mentioned the Occultum, which was actually a place and not an object. They came to an agreement, and Ruby hid it before she died.
After noting that Jo can't be trusted, Ruby agreed to tell Cas where the Occultum was if he helped her escape from the Empty. It turns out dreaming over and over about past regrets while eternally resting was pure torture. Cas told her he'd help her, which prompted Ruby to whisper the location in his ear. Before Cas could leave, however, he was stopped by the Empty, who planned to torture him since Billie never specified that Cas was necessary to complete her plan. Thank heaven for Jack, who pulled Cas out of the Empty before he could be tortured to death. Back at the bunker, Cas was met by Dean, who called him an idiot for going through with this risky plan.
Empowered by Cas' new lead, Dean decided that the Winchester doppelgängers would be useful after all. They would serve as stand-ins for the real Sam and Dean in case Chuck checked in on them while they were out chasing down the Occultum. Sam cast a spell to bring them to their dimension, and we learned a bit more about these alternate Winchesters. Things to note about their world: They don't like beer, John Winchester is alive and spoils them, they get paid to demon hunt, and they carry out the family business on their own private jet because they're filthy rich. In order to pose as our Winchesters, they needed to look the part, which meant Sam had to ditch the man bun and Dean needed to switch his dressy button-down for a casual flannel top. Needless to say, they were offended at the changes but agreed to play along.
While Team Free Will carried out their new mission, the alternate Winchesters were left to their own devices at the bunker. Sam refused to ditch the man bun because his hair was "sacred." Meanwhile, AU Dean found his counterpart's porn collection, which scandalized AU Sam, and noted that the Winchesters had it made. They didn't have to deal with all of the corporate nonsense of monetized demon hunting, like quarterly reports and investor calls. They simply hunted monsters, drank beer, and watched porn.
Elsewhere, Sam, Dean, Jack, and Cas arrived at the church where the Occultum was apparently hidden. Jack pointed out that this was too easy, and right on cue, hell hounds made their presence known with eerie growling. But the boys made it inside the church before they wound up as doggy chow. With the fearsome creatures threatening to tear down the door, the gang searched for the Occultum. Jack quickly found a round, silver object covered in markings that said: "To be in the Occultum, the Occultum must be in you."
Taking the phrasing literally, Jack swallowed the object, which then transported him to an idyllic garden of fresh florals and greens. It turned out the Occultum was actually the Garden of Eden, a place that humans could not enter. He was met by a young girl who led him to a tree with a serpent, who asked Jack two very important questions: Who is he really, and who is he meant to be? Those deep philosophical questions sent Jack into an emotional spiral, with the Nephilim reliving his darkest memories, including murdering Mary Winchester and breaking out of the malek box. He was then transported back to the church and awakened in the fetal position.
Back at the bunker, Dean ushered out the doppel-Winchesters and suggested they head out to Brazil next. Before leaving, alternate Sam revealed that he and his brother found it. Yep, AU Sam and Dean found the Impala and drove it, much to Dean's dismay. Brushing off the humorous moment, Dean checked in with Cas about Jack after his mysterious trip to Eden. Cas noted that something was different about their adoptive son, ushering them in to see him. Jack, an emotional wreck, immediately apologized to Sam and Dean for killing Mary. But this time, he really meant it. He felt remorse. It's only then that Cas confirmed what everyone suspected: Jack got his soul back. Jack then begged for forgiveness and the Winchesters, bearing pained expressions, looked on in silence.
Who else needed to hug a puppy after this?