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25 Days of Bingemas, Day 23: ‘The Holiday Sitter’

Hallmark’s first gay rom-com features two opposite personalities drawn together by their mutual hotness

Getty Images/Hallmark Channel/Ringer illustration

The Ringer’s 25 Days of Bingemas is a guide for people who love original holiday movies; it’s a guide for people who hate original holiday movies; it’s a guide for people who occasionally watch these movies and want more; it’s a guide for people who never hope to watch these movies but would like to watch one writer descend into madness as she attempts to differentiate between 25 unique forms of holiday magic, 12 different fake countries, and eight different male leads who make you wonder, “Wait, is that the guy from Mean Girls?” (It isn’t, except for that one time when it is.) Every day for the next 25 days, Jodi Walker will feature one of this season’s 169 original holiday movies, answering a curated series of questions in order to showcase the genre’s masterful formula, the dedication to chaos, and the commitment to consistently widowing lumberjacks that launched an entire genre of TV movie. On the 23rd day of Bingemas, we turn our cheerful spirits to …

What are we watching?

The Holiday Sitter.

Where are we watching it?

Hallmark.

Why are we watching it?

Because, per Hallmark, “When Sam, a workaholic bachelor, babysits his niece and nephew before the holidays, he recruits help from their handsome neighbor Jason and finds himself in an unexpected romance.”

How many Vanessa Hudgenses are in this?

There are no Vanessa Hudgenses in this movie, but we are provided with a different heartthrob of the aughts. The only thing I’ve personally seen Jonathan Bennett in since Mean Girls was an LIRR train car a few summers ago when even he was forced into standing room only. The Holiday Sitter was a much more pleasant experience for both of us. Bennett’s big-eyed goofiness is a nice balance to his love interest George Krissa’s “go girl give us nothing” approach to wooing. I also firmly believe that if these two harnessed the power of their megawatt smiles in the same direction, they could create a hole in the space-time continuum. (Inside that hole? All the fake towns and countries from Hallmark movies.)

How believable are the lead characters’ ostensible careers?

Sam has a vague job in finance, which I love. We don’t have to invest (pun intended) too much in figuring out his whole deal (it’s finance), and sometimes he answers the phone like this: “Hello? Duchess? Yes, we’ve donated all the funds to the children’s home anonymously.” Sure, that sounds like a job! Jason is a similarly vague contractor whose current job is remodeling a nursery for Sam’s sister, which seems to mainly consist of painting four walls a nice lavender color. So, I guess, I am also, on occasion, a handsome local contractor.

How problematic is the meet-cute on a scale of “one saved the other from falling in a snowbank” to “one is the other’s boss and they fall in love on a work trip”?

The Holiday Sitter marks Hallmark’s first gay rom-com, as the network has slowly worked toward diversifying the content of its historically very straight, very white oeuvre. Thankfully, the writers spare no expense in doling out the most classic Hallmark tropes: career-focused bachelor Sam meets family-loving local (alleged) contractor Jason when Sam’s sister unexpectedly needs him to come babysit his niece and nephew over Christmas. When Sam arrives on the icy doorstep in his city-boy boots, Jason the next door neighbor quite literally shows up out of nowhere to catch him in his arms as he flails through the air after slipping. They stare into one another’s eyes presumably thinking, “I’ve never met another person who was as hot as me before.”

Say, are these two opposites?

After actually talking, Sam and Jason discover that they’re complete opposites. Sam hasn’t been to visit his sister in years because everything about suburban family life gives him the ick. He’s still trying to live down the last time he babysat his niece and nephew, when he almost burned their house down, whereas Jason has known he wanted to start a family his whole life, and is beginning to look into the process of adoption as a single dad. Once Sam realizes how good Jason is with his niece and nephew, he asks if he can pay Jason to help him with this unexpected, unpaid, and unappreciated (hot take on a TV movie that premiered two weeks ago—this sister is kind of a villain) babysitting gig.

Does anyone almost kiss only to be interrupted?

Once Jason more or less moves in to play husbands with Sam, these two are never not almost kissing. (Except for the times when they’re just almost-holding-hands, an entirely new genre of foreplay.) Throughout the film, their near-kisses are interrupted by kids with nightmares, by Jason’s 20 family members that also all live in this neighborhood, and inexplicably, by headlights shining through a window as they sing “Silent Night” a capella around the Christmas tree while still, mid-song, somehow nearly kissing. At which point I screamed, “You can still kiss! You don’t have to not kiss because of headlights! KISS!!!”

Is there any singing/crafting/baking/blogging?

There is live theater in this movie, which is so sacred yet rare to the formula I dare not even keep it in my list of questions. Anyway, Sam’s nephew is in the community Christmas play, so Sam steps up to help him with his lines because he “used to be in a lot of Christmas plays.” Please understand that Christmas plays are a very specific form of acting, and they require a delicate touch. (On that note, I keep seeing an absolutely inscrutable preview for a Hallmark movie about actors performing in “a Christmas Eve courtroom production”—Oh, that old chestnut?!—where they act out a part-scripted, part-improvised debate over who wrote the Christmas poem, “A Visit From St. Nicholas.” It is my greatest Bingemas regret—and perhaps my greatest life regret—that I cannot cover this Christmas Eve courtroom production for you here.)

Is there any singing/crafting/baking/blogging?

There’s also quite a bit of baking in this movie as Jason teaches Sam how to make an edible breakfast over the course of playing house. That leads to, hands down, the most unintentionally hilarious scene in the movie, which went viral on TikTok because, out of context, it kind of makes it seem like Sam’s mother was killed by pancakes, his father knows it, and is intentionally trying to harm him with his breakfast order.

Did this movie make me cry?

In context, Sam is afraid he’s lost Jason and all the pancake privileges that came along with him. Jason wants to start a family, and Sam has always publicly eschewed the idea of children. But now that he’s met Jason, he’s able to envision a different life that he couldn’t have foreseen; before, Sam thought he looked for reasons to run from men who were interested in him, but now he’s found out he just needed a reason to stay. A reason such as a contractor with a heart of gold and eyes of Targaryen purple.

And listen, there’s some sticky stuff in there about just allowing characters to not want to have children, and not making that some character flaw they have to overcome … but that is simply not the priority of The Holiday Sitter. The priority of The Holiday Sitter is to be a sweet love story between two hot men. And I’ll shoot you straight, I somehow did not cry, but I think that might be because Jonathan Bennett was crying enough for all of us: sad tears, happy tears, heartbroken tears, pancake tears. The man saw his opportunity to take the emotional stakes of this Hallmark movie up a notch and said: watch this.

How modest are the wardrobe choices?

Far too modest! There are like six opportunities for these guys to strip their shirts off and paint a nursery lavender and they never do it once. It just goes to show: Hallmark has made some progressive strides, but there’s still plenty of room to grow, and plenty of abs yet to be seen.