Bobby, It's Cold Outside

"Bobby, It's Cold Outside" is the 10th episode of season 31. It aired on December 15, 2019.

Plot
Five weeks before Christmas, Lenny orders his Christmas gift online, and two days later United Parcel Service, UPS, carefully delivers it, but someone stole it before he could grab it.

At the lighthouse, Sideshow Bob is decorating his tree with decorations of dead Barts. He's visited by Cassandra Patterson, a woman who lives in the nearby lighthouse, bringing him muffins and flirting with him, asking for any dark secret and if he ever thought about children.

She tells him she mentioned him in town, and Bob knows he let his guard down around her when two men come visiting, but they offer him a job at the Springfield Mall as Santa. Meanwhile more people are getting robbed of their delivered gifts.

In the garden, Homer is blowing his Santa inflatable but to do it quicker he used the car's gas and blows it away in flames, burning the tree too, with Ned extinguishing it. Afterwards, Marge informs him they're going to Santa's Village with the kids and Homer tries to fly away like his balloon but Marge stops him.

The kids don't really have a great time at the start, expecially Maggie having to ride her feared Gnome in Your Home ride, the Gnome-in-the-Home Dome, where Gerald gets kidnapped too.

Bart skips the line to see Santa thanks to Milhouse and finds out the bad way who he really is. Bob tries to strangle him but he can't cause he can't step out of character, so Bart hits him with a fan and tries to show security who he's but fails and the family runs away when Homer finds out as an old Krings Kringle Union member, he has to pose to photos as Santa too.

When a plan to trick the robbers with gun powder fails for Lenny, he says to Carl who the culprit is, writing with his blood the letters SB. When the news gets on tv, Homer calls the cops to reveal that SB means Selma Bouvier and she gets arrested, freeing the held, and Sandra Bullock.

But Bart knows better, so he takes the bus back to the Village and finds the plan, but it's just his life goals. When Bob finds him reading it, to prove to Bart that he's not going to kill him, Bob agrees to help Bart find the culprit, by conceiling himself in a box and is placed on the porch.

The thief arrives and the family follows the van to a hangar, finding out Smithers and Mr. Burns were the culprit, and Lisa catches on why he did it, because he's depressed.

Mr. Burns tells the story of how he got heartbroken on Christmas, when he asked Santa just a hug and a smile from his parents and they never delivered, taking him to boarding school instead, and the next time they met they died (though his mother is seen alive in present time).

Bob reaches into his heart, reminding him how they made him strong as the biggest present. Burns and Smithers then give presents back to the people in town on a sled.

On Christmas Day, Homer and Marge snuggle together just before the kids open the presents, and they go to the basement to enjoy some time together, just after Grampa takes a picture to bless everyone with "Merry Christmas from the Simpsons!".

Back at the lighthouse, Cassandra brings Bob a Christmas present, a rake, and tells Bob that she knows who he is. She tells Bob that she wants him to kiss her before the two of them start singing "Baby, It's Cold Outside" together. She and Bob then sign a "Snuggle Contract" saying that both of them knew what they were getting into, just after Horatio McCallister crashes into a rock because the lighthouse light wasn't lit.

At the Springfield International Airport, Ballmer meets Mr. Burns. Burns asks him how he could be so positive about everything and asked if he could teach him how to do it. Ballmer then gives Burns a pep talk. When Burns tries to copy his motions, he hurts himself and has to be taken away in an ambulance, with Steve Ballmer going with him.