I didn’t know anything about this movie before I started it…except perhaps that one of the characters had the audacity to group Oatmeal Raisin in with actual Christmas cookies. Be warned, that DOES happen. Let’s dive in!
A truck pulls up to a big house with a gigantic tree. The Darlington house. Jessica is their assistant. Looks like there are three Darlington brothers. They have a lovely, GIANT living room. Jessica is going to start being one of their attorneys. That is quite a shift-assistant to lawyer? One of the Darlington boys, Charles asks her to meet with their family lawyer, Nina.
Their nieces and nephew are coming back from Australia. Their other brother and his wife died and now their current guardian, their great Aunt Matilda, has had some health challenges and can’t take care of them. So this brother and Max are going to raise them. Jessica seems skeptical about Max.
Max is skiing with his bros. He seems to just like living his life going where the wind takes him. Back at the office, Nina tells Jess all the details about the kids. Charlies is going to be in Europe all of December. He tells Jess that the kids will be going to boarding school over Christmas because everyone is too busy or sick to spend Christmas with them. So, all Jess has to do is get them to boarding school. Max is too busy skiing in Vermont. He seems to just bounce from Ski Lodge to Ski Lodge throughout the winter. Not working, just spending money. T
Max doesn’t seem to know about the boarding school plan. Wait so Jessica says she started the job as Executive Assistant 2.5 years ago? Instead of gaining practical legal experience she worked round the clock as an executive assistant? I mean, I guess it paid off for her but that is a dumb plan.
Later, Jess reviews a flyer for a Christmas Fair with her friend Zoey. She thinks the kids would probably like the Christmas Fair. Later, Jess looks up the boarding school the kids are going to.
The next day, Jess goes over Charles’ schedule and the details of the Christmas Party. EVERYTHING NEEDS TO BE PERFECT. Charles is working on a deal with Victor Lee. A big Christmas party is going to be crucial to securing this big deal.
Max arrives at the office. He is very clearly an absent “President.” He has a bone to pick about the Peyton Academy boarding school. He wants to be involved in the decisions about the kids. Max wonders if there is anywhere else they can go. Charles is like, who is going to watch them? Then, Jess offers to watch them over her vacation. She says she knows what it’s like to be a kid alone at Christmas. Then Max agrees to help too.
Jess has a fireplace IN HER OFFICE. Dude, I would be an EA for that. Jess and Max strategize about having the kids. Jess wants to give them an old fashioned New England Christmas. Oh I am so sad for these kids.
The next day, Jess and Max wait at the airport for the kids. She brought their Christmas presents to the airport. Why? The kids arrive and are very polite and well mannered for being sent across the world right before Christmas. Okay, they hand the kids some welcome gifts. They all got Christmas sweaters. Just what every kid wants! Oh, the little one, Abby, does love it.
They arrive at the house and meet Mrs. Brooks. The kids remember her. Max takes them up to their rooms. Jess and Nina talk about how hard it’s been on the kids.
Mrs. Brooks and Jess chat downstairs in the kitchen. That’s a pretty basic kitchen for such a wealthy family. Mrs. Brooks talks about how hard it was on the Charles and Max when Jared, their brother died. She thinks that’s why both brothers are gone so much.
Max goes in to check on the girls and he can’t find them. He finds them all in their brother’s room. And they all wanted to stay in their dad’s old room.
Then we get a little sense of Max and Jess’s personalities. She wants to make a list of FUN Christmas activities. He wants to just see how things go. So he is a free bohemian spirit and she is…not.
The next morning, Max oversleeps! The rest of the crew are downstairs having a formal organized breakfast with everything beautifully spread out on the table. Are they all going to eat cold waffles because they were waiting for Max?
Jess asks for their ideas for fun Christmas activities. One of the girls suggests decorating a Christmas tree. But their interior tree is already decorated. They decide to go get another tree. Jess’s idea is to decorate a tree outside with ornaments that animals can eat. She used to do that with her mom. I actually love that idea.
They head back to the kitchen to make the ornaments. MONTAGE TIME. The older sister. Emma, does a lot of parenting and helping it seems. She says they’ll be alone again when they go to boarding school. Abby says, “that’s okay! We can handle it!” Sad.
Then, Max organizes a carriage ride. The oldest sister, Emma likes to read about horses and ride. They kit a bump and Jess gets closer to Max. After the ride, Jess shares that she doesn’t have any family to spend Christmas with. The kids realize that their grown ups are like them. Well aren’t they all a sad little bunch? Then, they decorate all the trees outside. So cute!
Jess calls Zoey on the phone. She fills her in on the day before. Zoey asks what he’s like. Then Jess reads an article about Victor Lee, the important businessman they need to impress with the Christmas party. He likes family! Not fancy! The party will NOT impress him. Uh Oh. And the only solution is to change the theme of the party because Christmas parties are what make or break big deals.
Later, the Darlington crew stroll through town. The boy sees a shop full of JUST PUZZLES. I guess it is a toy store. Max takes him inside and Jess takes the girls for hot chocolate. The boy (I never catch his name) quickly calculates how many hours it will take to do the puzzle he picked out. The shop owner blabs that Max usually buys all the toys in the store for the Boys and Girls Club but likes to keep it anonymous. Oops. Did he just say that out loud?
Jess and Max tell the kids that they have to change the Christmas Party plan to accommodate that potential…investor or client or whatever? Emma says they should have it at a house. Max says they should just have it at the house. Max gets that classic whipped cream mustache. FUNNY GUY. Max tells Jess to tell Charles about the changes to the Christmas party. Max doesn’t think Charles will listen if he thinks the idea comes from him.
The next day, they whip out the puzzle. Max is all in on helping. Meanwhile, Jess fills Charles in on the new plan for the party. Again, this whole deal hinges on an impressive party. Jess gives credit to Max for all of the new ideas. Jess also wants to invite the families of the employees. Charles doesn’t want it to look like a circus. Amen, brother. He agrees. Then Jess checks in with Nina. Jess asks her how she got into family law. She was inspired from personal experience. Jess shares some of her experience and how she ended up taking the job at Darlington. The family law attorney tells her she would be a great family attorney.
Jess gets back tot he house in time to see the whole gang baking Christmas cookies. Uh oh. Jess puts on an apron and asks where the raisins are. WHAT. She wants to make oatmeal raisin cookies. KICK HER OUT OF THIS HOUSE AND FIRE HER. Is anyone’s favorite cookie oatmeal raisin?
Emma says her favorite thing is toffee. Mrs. Brooks has her mom’s recipe! She shows it to her and it’s in their mom’s handwriting. Oh that’s very sweet.
Later, Max makes grilled cheese and tomato soup for Jess and himself. That sounds good. He opens up a little about his life choices and all that. Jess shares a little about herself too. Max says she is part of their family.
The next day, gang heads to the Christmas Fair and they all brainstorm ideas for the party. Jess sees Zoey. Zoey is spiraling about the barista she likes. Zoey recognizes Max from volunteering in the pediatrics ward. She didn’t realize he was a Darlington. Zoey is like, you should have a crush on him, okay.
Then they all do Christmas crafts together at this fair. Max says Zoey looks familiar. Jess says she knows about his sneaky volunteering. He says you should do the right thing because it’s the right thing; not to brag about it.
Later that night, Abby comes in to Max’s room and says she has a nightmare about a fish. She asks him to read her a story. She’s got the Wizard of Oz all ready. Jess encounters Emma in the hallway. She is looking for Abby. All these kids out of bed in the middle of the night is stressing me out!! They carry sleepy head Abby to her bed. Emma is still awake! Go to bed girlfriend! Emma says Abby usually goes to her when she has a nightmare. She is worried that Abby is getting too attached when they are about to be shipped off to boarding school. Max reassures her that this is their home when they’re not in school. That seems to help for now.
Max and Jess chat downstairs. He tells her how they weren’t ready to be guardians when his brother died but he wants to be more involved. He really loved Jared. Charles must be quite a bit older than Max because Max says he already had his own life when Max showed up. He feels that after everything Jared did for him growing up, he owes Jared’s kids a good Christmas. Mrs. Brooks walks down and interrupts for no reason. After Jessica goes to bed, Mrs. Brooks tells Max not to “mess this up.” She knows he’s liked Jessica for a long time! Max thinks she doesn’t take himself seriously.
In the next scene, the street sign is TOTALLY BLANK. Jessica admits to Zoey that she has a crush on Max. Zoey tells her that she is too cautious. She didn’t used to be!!
Jessica comes home. Max has just opened a package with the kids’ uniforms. The kids see them and are very polite about them but sad. To lighten the mood, Jess suggests they make snowmen. They have a little snowball fight and run right into Charles! The kids fill him in on all the fun they’ve had. Charles is surprised that Max has been so good at parenting and everything. Max takes this opportunity to ask Charles to talk about his role at Darlington. Charles asks if they can talk about it later. He is SO TIRED.
It’s party time! The girls look so cute. The boy needs help with his tie. So Max helps him out. Zoey arrives with the barista, Kate. Zoey tells Max that Jessica has been having a great time with him. Jessica sees Nina and walks over to chat. She says she can’t be a family law attorney because she doesn’t have any experience. She’s been an executive assistant the whole time she’s been in law school so she doesn’t have practical experience in any field! She’s lucky anyone wants to hire her!
Max runs into Victor. They share a love of some random winter vacation spot. Victor wasn’t aware that Darlington was a family company! The party makes that VERY CLEAR. Then, Charles shows up and wants to introduce Victor to the other board members. Charles tells Max to do what he does best-have fun and not worry about Victor or this deal. So Max goes outside and stares at the trees. Jess joins him. She gives him a nice pep talk and says she believes in him. Then Abby bounds out and says she made more ornaments.
Victor Lee comes out and sees the trees. Jess says “Merry Christmas” in a language he also understands. Abby does a good job inadvertently reinforcing how family oriented they are.
The next morning, Charles shares some good news. Victor Lee picked them to…do business things with! The Christmas Party won him over. There is no other reason. Victor told Charlies he really liked Max and wants to meet up with them next month at that vacation spot. Charles apologizes to Max and says that Victor wants Max to be the liaison for their company. So now Max gets to “run the Taiwan” division. He would be in Taiwan on a more permanent basis. Oh yikes! He will miss Christmas with the kids!
Jess and Max talk about what a great opportunity this is. They both seem sad. And they realize they have to tell the kids. The kids seem bummed. Jess says she’ll stay for Christmas though.
Max gets ready to leave. The kids all say goodbye in their Christmas sweaters. Oh, they have like 5 pieces left of their Christmas puzzle. How can he leave before that’s done? Outside, Max dramatically pauses and looks at his family before getting in his car to drive to Taiwan. Jess stares after him in the driveway.
Max sits at the airport and sees a family walking by. They must have muted the parents yelling at their kids to hurry up or stop whining or remind them that no, they just had a snack or tell them we have to get our gate first. He doesn’t hear any of that so he feels wistful instead of relieved to be traveling alone. He decides to make a pro and con list of staying versus leaving.
The kids all say they like it at the house. Emma reminds them they’ll get used to Peyton as well. Jess goes in to Charles’ office to talk to him about boarding school. She thinks the kids should go to Riverside school instead, which is just down the road. She says she can take care of them. He’s like, you would give up your career? She’s like, no, it’s the 21st Century, dummy. People (EVEN WOMEN) can work AND raise children. The choices aren’t boarding school or quit her job you silly goose!! She wants to figure something out because she loves them too much! Charles agrees. Charles says Nina was right about her being a good advocate for children. He asks why she turned Nina down? She says it’s because she has a job with them! And they’ve treated her really well. Then, he gives her permission to work for Nina. So then, Jess gets a big gust of courage and tells Charlies she’s leaving to be bold and brave. So he needs to watch the kids.
Jess runs out of the house and calls Max. He doesn’t answer. Then she tries Nina. She leaves a message accepting her job offer. She passes Max in the driveway. She says she was on her way to stop him at the airport! He’s like, you’re being impulsive?! And then he shows her the little list he made about the pros and cons of staying. Then he says he’s been in love with her for 2.5 years. And they KISS. TWICE. Wow they love each other. Okay.
I notice Charles’s sweater for the first time. Charles is like, what is the deal, dog? Why are you back? Max says he wants a bigger role at work but he wants to be with the kids and Jess. Especially during Christmas. He wants to figure out a way to travel to Taiwan less. Charles is like, Mr. Lee wants you to be the liaison. So you can be the liaison. Max advocates for the kids to stay home too. Charles is like, I already know that.
They finally finish that blasted puzzle and have lovely little Christmas. Charles makes a toast to everyone…and Christmas. And that’s it!