The Holiday Sitter: 7+ Thoughts I Had While Watching Hallmark's New Gay Rom-Com

Jonathan Bennett and George Krissa in The Holiday Sitter
(Image credit: Hallmark)

Since 2020, Hallmark has been diversifying its content to include more varied stories about love. This includes more movies featuring people of color as leads and more LGBTQ+ representation. In 2020, Hallmark debuted its first same-sex couple, and now the network’s evolution has led to an entire rom-com with a gay couple as the focus. The Holiday Sitter debuted on Hallmark on December 12.

The Christmas House was the first Hallmark movie to feature a gay couple prominently, but The Holiday Sitter is their first film centered around a gay couple. I really enjoy great Holiday rom-coms, but don't regularly watch upcoming Hallmark movies and am no expert. Therefore, I haven't seen many of the channel's best, but I’ve seen enough to know some of their characteristics, traits, and style. 

I went into The Holiday Sitter expecting a light, fun holiday romance. That’s what it achieves. However, it was even better than expected. Here are some of my thoughts while watching The Holiday Sitter. 

Warning: The Holiday Sitter spoilers ahead. Proceed with caution.

Jonathan Bennett and Chelsea Hobbs in The Holiday Sitter

(Image credit: Hallmark)

The Holiday Sitter Is Silly On Purpose 

The Holiday Sitter doesn’t take itself too seriously. It knows at its core, it’s a romantic comedy with a big emphasis on the comedy. It knows how to balance cartoonish comedy, subtle comedy, and those serious moments when necessary. Jonathan Bennett is an actor who very much uses his expressions to communicate. 

He knows how to exaggerate his eyes, pull a shocked face, and throw his whole body into a gag. It’s a talent that he effectively utilizes here. Sometimes movies don’t understand how comedy works and do too much of one thing and not enough of another. This one knows its audience and knows how to make a fun movie that’s just the right amount of cheesy. It, and many other great Hallmark films, don’t want you to think too hard. It’s all about enjoyment. The Holiday Sitter is perfect for a night of relaxing and enjoying a fantastical story about love.

Everett Andres and Bella Leonardo in The Holiday Sitter

(Image credit: Hallmark)

This Movie Feels Like Every Character Is Living Their Own Hallmark Movie 

Many of the movie’s cast has appeared in other Hallmark movies. I may not have seen their others, but you get the vibe that these actors and actresses are quite familiar with the format. Many of them also have character traits that you may see in the network's other films.

For example, one of Jason's (George Krissa) brothers is a divorced dad. That could easily be a Hallmark movie on its own. Then you have Sam’s (Jonathan Bennett) father who often lives off the grid. That’s another one. Then you have Jason’s seven siblings and eighteen nieces and nephews. Theirs could also easily be its own story for the network. 

Let us also not forget that Miles (Everett Andres) and Arabella (Bella Leonardo) have crushes on each other. A spin-off movie could take place ten years from now when they meet again after college when they return home for Christmas. There you go, Hallmark; another movie idea! The Devito, Dalton, and Walker families have so many characters that could have their own romantic movie. 

Jonathan Bennett and George Kriss in The Holiday Sitter

(Image credit: Hallmark)

Did Hallmark Get A Budget Increase? 

As stated, I have yet to see many of the channel's films, especially many of the new ones. Therefore, I don’t know if it’s the norm now, but The Holiday Sitter feels like it has a decent size budget. It looked very crispy and HD—quite a camera quality improvement. The script feels a little bit wittier, fresher, and more self-aware than some of the Hallmark movies I’ve seen in the past.

It seems like they've put more money into not just creating many films but also really good ones. I was impressed by the production.  

George Krissa and Jonathan Bennett in The Holiday Sitter

(Image credit: Hallmark)

I Now Need Weekly Updates On Sam And Jason’s Relationship 

I would say that many of my favorite films are rom-coms. I have seen many of the best romantic comedies, and some not-so-great ones. However, it is very rare that I get to the end of one and want to know what’s next for the leads. I’m perfectly content with just assuming that nothing bad ever happens for them, and they go off to live their happily ever after.

At the end of The Holiday Sitter, I wanted to know what was next for Jason and Sam. Not only are they a cute couple to watch, but a lot could go wrong in their relationship. However, they feel like the type of fictional couple that can tackle any obstacle standing in their way. I want to know how they navigated these obstacles, especially Sam being “maybe” about wanting children.

I am also nosey and want to see more of their big moments, like, hopefully, a wedding. 

Jonathan Bennett in The Holiday Sitter

(Image credit: Hallmark)

Sam Is Almost Too Good At Mastering Skills 

My one major issue with The Holiday Sitter is Sam’s ability to master things so easily. He went from bad uncle to great uncle, he could easily mentor his nephew from being a bad actor to a good actor, and somehow he went from a contestant on Worst Cooks in America to a Masterchef. I don’t buy it. 

He needs to be bad at a few more things to feel a bit more realistic. Also, what is the holiday movie obsession with bad cooking? First, we have Sierra in Falling for Christmas and her cooking montage, and now Sam watching one cooking demonstration and becoming an expert

Anyone as bad at cooking as they were would need more practice before becoming great home cooks. 

Jonathan Bennett in The Holiday Sitter

(Image credit: Hallmark)

You Can Tell Hallmark Wanted To Get Representation Right  

Sometimes scripts feel like they were written with no specific gender, race, or sexuality in mind. They just plug and play whoever they cast in the role and don’t consider more than that. This can work sometimes. Other times it doesn’t help tell an authentic story. Clearly, The Holiday Sitter was always written (or at least altered) with a gay couple in mind. It doesn’t feel like this script was originally written about a straight couple, and then they changed it to be more inclusive.

There are so many subtle touches that show that the screenwriters wanted to tell an LGBTQ+ love story in a genuine way. Things like Jason coming out to Sam by recognizing his designer shoes, and Sam’s speech about being told no for so long that it’s taking a while for him to adjust to his new possibilities give the film a distinct identity. 

These moments really make it stand out and highlight some struggles that LGBTQ+ people may face. 

Chelsea Hobbs and Matthew James Dowden in The Holiday Sitter

(Image credit: Hallmark)

The Holiday Sitter Tackles Real-World Issues With Care 

The movie sprinkles some really serious topics into an overall lighthearted film. It showcases a family with infertility issues and does so in a casual way. They are a family even if they may not all share the same blood. It also shows characters who are divorced. One of the ongoing jokes about Hallmark movies is that characters are often widows. 

This movie shows that sometimes people just get divorced and still thrive. We also get Jason’s desire to adopt and start a family. It doesn’t go into details, but you see some of the struggles he faces in that process, such as making sure he has enough money to cover all the fees. 

It's quite a realistic Hallmark movie. This makes it even more powerful because it shows that things don’t have to be perfect for a happy ending. 

Jonathan Bennett and George Krissa in The Holiday Sitter

(Image credit: Hallmark)

Other Thoughts  

Ay, another Mean Girls reference. Let us discuss.

  • This is really a great year for Mean Girls and holiday movie fans. First, Lindsay Lohan, then Jonathan Bennett, and we all know Lacey Chabert is one of the queens of Christmas movies and is an actor staying with Hallmark.
  • Sam giving Jason money definitely felt sleazy even if that was their original agreement.  
  • Who knew quietly singing “Silent Night” could be romantic?  
  • I am really glad this took place in a suburb and not a small town. This means that neither Jason nor Sam need to move to be together.  
  • If there is The Holiday Sitter 2, it needs to take place in Hawaii. I kind of wanted Sam to get his tropical vacation.  

The Holiday Sitter and many other original Christmas films are really making this a great year for holiday movies. 

Jerrica Tisdale
Freelance Writer

Spent most of my life in various parts of Illinois, including attending college in Evanston. I have been a life long lover of pop culture, especially television, turned that passion into writing about all things entertainment related. When I'm not writing about pop culture, I can be found channeling Gordon Ramsay by kicking people out the kitchen.