Stream It or Skip It: ‘The Holiday Sitter’ on Hallmark Is a Perfect Vehicle for Jonathan Bennett

Hallmark is ready to make history with The Holiday Sitter, the network’s first-ever holiday romcom with a gay couple in the lead roles. After championing inclusion as part of The Christmas House 1 and 2’s family ensemble, Jonathan Bennett gets the starring role as a bachelor who learns that he just may be up for settling down. Is The Holiday Sitter the start of a bold new trend for Hallmark? Or is it… nah, there’s no other option here. It’s the start of a bold new trend, no matter what.

THE HOLIDAY SITTER: STREAM IT OR SKIP IT?

The Gist: Jonathan Bennett plays Sam Dalton, a proud bachelor working as, like, a wealth consultant for top-tier clients? Basically rich people hire him to keep track of their expenses and talk them out of buying things like yachts and tigers. Sam’s ready to spend Christmas flying solo in Hawaii — and then he gets an offer he can’t turn down, even if he would really like to. Sam’s sister Kathleen (Chelsea Hobbs) and her husband Nate (Matthew James Dowden) have to hit the road because the baby they’re adopting is arriving earlier than expected. Who can take care of Kathleen and Nate’s two kids, Miles (Everett Andes) and Dania (Mila Morgan)? Who couldn’t possibly have any plans this close to Christmas? Sam, that’s who!

Sam postpones his holiday in Hawaii and hightails it to the suburbs where he meets Jason DeVito (George Krissa), Kathleen’s handsome, single, and gay neighbor. Kathleen neglected to mention Jason because she knows how commitment-averse her brother is, and she knows that Jason is about to start the process of adopting a child. With Jason’s help, Sam learns how to guncle like the all-time greats … and maybe he’ll also learns that this family thing ain’t so scary after all…

What Movies Will It Remind You Of?: There’s a bit of Three Wise Men and a Baby in here, another one of this year’s surprisingly original Hallmark movies. And while The Holiday Sitter has the zip and charm of our fave Hallmark holiday romcoms, it really does offer something completely unique.

Performance Worth Watching: This is George Krissa’s second Hallmark movie, following a supporting role in May’s Road Trip Romance, and hopefully it’s just the beginning of a prosperous partnership. He really has a stoic charm to him that makes him seem mature and mysterious at the same time — but he also has the smile of a Hallmark romance lead. Hallmark needs to start building out its roster of queer leads, and here’s hoping Krissa gets to find love in a movie of his own next year.

Memorable Dialogue: When Sam finds out that the vegan pancake place is closed, thus dashing Dania’s breakfast dreams, he says to Jason, “Apparently it’s vegan pancakes or deep sighs of disappointment followed by a face I usually only see right before someone breaks up with me.”

A Holiday Tradition: Sam’s nephew Miles gets a role in the annual Christmas play, The Life and Times of Santa Claus; there’s the usual Christmas market (but no tree lighting, at least that we see); and we get a new tradition in the form of a Christmas lights walk. That’s where you walk around looking at Christmas lights.

Two Turtle Doves: As mentioned above, you can definitely pair this with Three Wise Men and a Baby, another stellar Hallmark entry from this year about men learning how to take care of a child. You could also wait until Friday, December 16 and pair The Holiday Sitter with Lifetime’s gay romance Christmas movie, A Christmas to Treasure (starring real life spouses Taylor Frey and Kyle Dean Massey).

Does the Title Make Any Sense?: Yes, it does. I think The Holiday Sitter is slightly better than The Holiday House Sitter, which is a mouthful. And it’s better than The Christmas Sitter, which — say it out loud and try to not sound like Randy Quaid in Christmas Vacation while he’s emptying his RV’s septic tank.

Our Take: I mean — it’s great. It’s not the most original Hallmark movie of the year, nor is it the funniest, nor does it have the most star power — but The Holiday Sitter is great in all of the ways that it needed to be great. Because — to get the serious stuff out of the way up top — America needs to see queer couples in holiday movies, Candace.

Like I said about The Christmas House in 2020, including queer people (which, BTW, should include more than just cis, white, gay men) in family content like holiday movies helps the “gay agenda” tremendously — the “gay agenda” being us wanting to… continue to exist. If you’re from the South or the Midwest, or just the rural parts of any state, then it’s likely that your mom and dad don’t watch We’re Here, grandma won’t watch Queer Eye, your somehow-even-more-religious aunts and uncles won’t watch Drag Race — but they all watch Hallmark holiday movies. And if they watch The Holiday Sitter, they’ll see that it is possible for two men to fall in love while making pancakes, decorating stockings, and singing “Silent Night.”

So yes, on that level, The Holiday Sitter absolutely gets the job done. But I want to talk about two specific successes that make this movie stand out. First, there’s the Jonathan Bennett of it all. Hallmark has a lot of fan favorite male leads, but Bennett is a new kind of leading man. He seems like the first leading man who gets top-billing in his movies because he has name recognition outside of the Hallmark channel. That’s the kind of star power that is, to my knowledge, only wielded by the network’s women (Lacey Chabert, Tamera Mowry-Housley, Jodie Sweetin, Holly Robinson Peete).

I really love this for Bennett because he is absolutely on the same level as all of those Hallmark heavy-hitters. Watching him in The Holiday Sitter, I noticed how this script and this role really played to his comedic strengths. There’s an over-the-top, bug-eyed look of worry that Bennett does that reminds me so much of Lucille Ball. Bennett isn’t afraid to look goofy, to fall into a Christmas tree or be flummoxed by an oven. He’s already a pro at this vibe, and it’s exciting to see where he’ll go next year and beyond.

The other major success: this is a storyline that could only be done with a gay couple. They didn’t just take an existing script and change “Samantha” to “Sam” — or, I mean, if they did, they went in and renovated every page. The Holiday Sitter is a Christmas movie about the incredibly unique bond between gay men and their nieces and nephews — family members who have long stood in for children due to the hurdles facing gay couples or gay men looking to adopt. And the chat between Sam and his sister towards the end of the movie, the one that explains why he’s always been terrified of having a family? No spoilers, but it’s a wonder seeing a common lived experience for so many members of the Hallmark audience finally reflected on screen.

And on top of all that, it’s just a fun movie. What a gift.

Our Call:  STREAM IT. Hallmark has donned the gay apparel, y’all.