No turning back.
While getting ready for game night at the bunker, Dean has an alarming voicemail from Donatello – begging for help before speaking a mysterious language. Dean and Mary rush to his home only to find Nick waiting for them. He has Donatello and injected him with a lethal dose of poison. If they want to find him they have to give him what he wants. With no immediate options, Dean and Mary take Nick back to the bunker for some light interrogation. Sam wants in but Dean knows that his brother needs to sit this one out after what happened last time. Sam reluctantly agrees but Dean doesn't have much luck beating Donatello's whereabouts out of Nick so they give into Nick's demands and let Jack talk with him – alone. Things go from bad worse very quickly when Nick accuses Jack of not having a soul and headbutts him when the young Nephilim gets close; setting Jack and taking the interrogation down an even darker path. Elsewhere, Castiel has made contact with the angel, Anael, in the hopes that she can help him contact God. It's something he hoped wasn't true but deep down, he knows that Jack has lost his soul and the only being capable of restoring one is God himself. After getting Donatello's location from Nick, Dean and Sam head out to save their friend with a handcuffed Nick in the back seat. Dean manages to find Donatello but not before Nick springs his trap. Every step of the way, Nick was getting closer and closer to bringing Lucifer back from the void.
It's been a few off weeks for Supernatural but Game Night finally nailed the tone of the final episodes for season fourteen. While Supernatural often has more than one story going that tends to be at the expense of the other, Game Night's stories worked in parallel to strengthen Jack's motivation and deliver message that the Nephilim has lost his soul and may be too far gone to save. Since he killed Michael and absorbed his grace, Jack has been slipping more and more into the realm of sociopath: looking for a place to fit in but feeling no guilt or remorse for any of the actions that he has taken. While not as exciting, Castiel's story slowed the pace in a meaningful way, showing he is desperate to help his adopted son and fears the worst knowing Jack has lot his soul. I'll admit, I wasn't happy to learn that Lucifer had woken up in the void but it was very satisfying to see him thrown right back in by Jack. It closed the door (at least temporarily) on that character and lead to Nick's demise (probably not). The excellent pacing between the two stories and how well Castiel's story foreshadowed the final three episodes of the season that helped pull everything together. Jack's story has taken a turn for the worst and Game Night made that happen in spectacular fashion.
If there's anything to knock on Game Night is has to be how obvious it was that something terrible was going to happen to Mary. Mary has been an afterthought this season and largely absent as of late. Her touching moments with both Sam and Dean made her a dead wringer to...die. Considering everything happening with Jack, his actions to Mary are the quickest and way to turn him from the well-intentioned boy to the soulless monster the Winchesters may see him as. Besides that, the only other slight is that Supernatural lore on the soul has largely been a complete miss and doesn't adhere to any rules until it suits the story. In this case, Jack has no soul and feels no remorse for whatever terrible action he feels he needs to take – but Nick does have a soul. It's never been questioned that Nick has a soul yet he murdered a lot of people and has done things far worse than Jack has. My point being is that Supernatural has never really defined what it means or doesn't mean when someone has a soul, just that it's bad because reasons. It was never clear when Sam lost his soul or even how Donatello has no soul but still isn't that bad. They feel nothing but that doesn't automatically mean terrible things.
Overall, Game Night is a solid episode of Supernatural that probably had the best entrance for Lucifer we have seen and a pretty gruesome death for Nick (possibly). Whatever happens next, things don't look good for Jack and the Winchesters may not be able to stop him. We'll see what happens next week when Supernatural returns in Absence.