If Dean was still on the fence about forgiving Jack and allowing him to fully resume his place in their erstwhile family, a visit from a wood nymph named Mrs. Butters changed that.
Supernatural Season 15 Episode 14 introduced a new character who has a place in the history of the Men of Letters, and for a while, she was great fun.
But when lessons are to be learned, even good times must come crashing down around Sam and Dean.
It's easy to appreciate how easily Dean wanted to succumb to Mrs. Butters caring for them. He's always longed for the family he remembers so little of and that Sam doesn't remember at all.
They missed out on so much normalcy during their lives, things the rest of us take for granted.
Holidays can bring out the worst in us sometimes, but could you imagine a life when you didn't use those special occasions to celebrate what you love about life?
Mrs. Butters was right about a lot. They need to take time to smell the roses now and again so they don't get too caught up in the overwhelmingly negative things they encounter almost daily.
Dean has always done that better than others. He's quicker with a joke and always eager to taste the next, best burger he's never had. There are simple pleasures that Dean enjoys that he always allows himself, no matter how frenzied their lives become.
If we look at Sam and Dean as parents with traditional roles, Sam would be the father figure and Dean would be the mother. Sam errs on the side of caution, and that was no different with Mrs. Butters.
It took Dean egging on Sam to accept her and her joyous attitude first, and look beyond that only if something went wrong.
Of course, we knew that Sam's spidey senses were tingling because something was bound to go wrong with Mrs. Butters.
But at the very least, she was acting aggressively not because she's an aggressive person but because she swore to herself to protect the Men of Letters always, even if she didn't fully understand what she was protecting them from.
Jack's soul has returned, and at the beginning of "Last Holiday," he was still cooped up in his room, contemplating all he had done and all he had to do to save the world.
He's rightly concerned that there's a lot that could go wrong.
But he was also feeling Dean's wariness, and that was dragging things down a little more, too.
Introducing someone who would, at least initially, care for them all put Sam, Dean, and Jack on equal footing. They could take a momentary pause from caring for each other and get stuff done without worrying about everything from household necessities to allowing any of themselves not to feel supported in any way.
Mrs. Butters not only had magic, but she was magical for the boys, who needed a little mothering.
Even when Mary was alive, they were all still so focused on the world at large that they barely got to appreciate the second chance they received they were all reunited.
Heck, even Mrs. Butters understood the importance of second chances and making the most of them, but that was before she understood the potential peril Sam and Dean might suffer at his hands.
It was so fun seeing everyone getting along, slaying monsters, and enjoying life's little pleasures that have passed them by. It's too bad that we didn't get to see more of those festive encounters.
Seeing them all open presents that they hadn't bought each other on Christmas, or shooting off fireworks like little kids, or Dean standing around with pumpkin guts on his hands as he carved a pumpkin would have all been welcome.
But, you take what you can get, and just like the boys, we were pulled from that reverie too soon when Mrs. Butters decided that to protect the Winchesters, Jack had to go.
To be fair, she has a very bad teacher in Mr. Cuthbert. He taught her that violence was an answer, which would ordinarily seem to go against her beliefs. She's kind hearted and caring, but she was used to dispense of enemies. That's cruel.
Mrs. Butters didn't understand what Jack meant to Sam and Dean, nor did she understand his importance to the world. But Sam's appeal that hurting people they care about goes against her desire to protect started to chip away at her game plan.
Thankfully, they managed to get the whole situation under control before anything irreparable occurred. It would have been great if they could have found a way to work together to save the world, though.
You can't argue that Mrs. Butters' powerful magic would have been beneficial in a battle with God.
But if nothing else, her visit reminded the bunker boys what they appreciate about each other. Even while in mortal danger, Dean allowed Sam to continue his date with Eileen, deciding to wait for his return naturally to intervene with Mrs. Butters instead of calling him home abruptly.
Someone threatening Jack also reminded Dean that he cares for him even if he's having a harder time forgetting than he would like. Their lives aren't ideal, but they work, for the most part.
And Dean's love of the apron came in handy to help Jack celebrate his birthday. The cake was a visual disaster, but it was made with love. What more could anyone want from a birthday?
For Jack, he's beating himself up over how easily he fell for Mrs. Butters and her charms and home cooking, worried that if he rolled over that easily for her, he's not going to be a match for God.
Except after 15 seasons, we don't have any doubt that this is going to end well. Because the alternative, after so long loving and caring for this family, isn't palatable.
Is it possible? Sure. But my bet is on the fact that Sam and Dean have done more for the world than anyone ever should have to do, and a happy ending is on the way.
What did you think of "Last Holiday"?
Are you just here to enjoy the ride while it lasts and the Winchesters ride off into the sunset?
Don't forget that you can watch Supernatural online right here via TV Fanatic, and share your thoughts in the comments below.
Carissa Pavlica is the managing editor and a staff writer and critic for TV Fanatic. She's a member of the Critic's Choice Association, enjoys mentoring writers, conversing with cats, and passionately discussing the nuances of television and film with anyone who will listen. Follow her on Twitter and email her here at TV Fanatic.