Jonathan Bennett | Holiday Sitter, Producing, + On-Screen Dynamics

Making breakthroughs for queer representation.

Written by

Jess Ferguson

Photographed by

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Styled by

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George wears Alexander McQueen shirt. Jonathan wears Alexander McQueen shirt.

Eighteen years have flown by since Cady Heron in the ever-quotable Mean Girls told Aaron Samuels it was October 3. Actor Jonathan Bennett has paid homage to his breakout role since then, starring in Ariana Grande’s pop culture tribute music video for “thank u, next” and publishing a parodic cookbook with celebrity chef Nikki Martin called The Burn CookBook in 2018. Although Bennett primarily started as an actor, he’s also recently taken on roles like producing, podcasting, activism, hosting, and entrepreneurship. His charisma as Aaron translated to hosting Food Networks’ Cake Wars for several years and competing in Dancing with the Stars. Now, he’s making history with his most recent project, The Holiday Sitter, as Hallmark’s first holiday romantic comedy with LGBTQ+ characters at the forefront, releasing December 11. After publicly coming out in 2014, Bennett has made other breakthroughs for gay representation—like his iHeart podcast PRIDEcast, and his travel company with his husband Jaymes, OUTbound, which offers worldwide cruises to gay travelers. 

We caught up with Bennett on The Holiday Sitter, working with his co-star George Krissa, taking on producing, and managing a work-life balance. 

George wears SARAI BESPOKE pants and vest. Jonathan wears Thom Browne sweater and pants.

What can you tell us about The Holiday Sitter

I’m so proud to executive produce and star in Hallmark Channel’s first Christmas rom-com that features LGBTQ+ characters as the central storyline. Not just because we are making history, but because of how hilarious and heartfelt this story is. My character, ‘Sam,’ is living the eternal bachelor life when he gets roped into coming home to take care of his niece and nephew for Christmas. He meets the handsome handyman living next door and sparks fly. I love physical comedy more than anything in the world and in this movie I got to do so many things I’ve always wanted to do in a movie…like knock over and fall into a 15-foot tall Christmas tree just to get the laugh. What makes The Holiday Sitter so special is the humor and the heart. It's filled with so many touching moments that make me still have butterflies every time I watch it, and as a gay man, I never had these touching holiday moments represented on screen growing up, so I think that’s why this movie, although a comedy, makes me so emotional. What I love most about telling this story is that yes, The Holiday Sitter is a gay lead rom-com, but it’s a love story for everybody. Just like Christmas is for everybody, The Holiday Sitter is for everybody. 

How was the dynamic of working with your co-star George Krissa?

Casting the perfect actor to play ‘Jason’ is something that kept me up at night for months. The actor had to have so many different qualities in my vision for ‘Jason’ that I was afraid we’d never find him. He had to be hunky, my height or taller, have blue eyes, be good with comedy, be charming, be able to sing, have that X factor on screen; the list goes on…Then I saw George Krissa’s tape and I called my husband and then the other producers and said, “WE FOUND HIM!” Working with George was such a blast for so many reasons, we had amazing comedic chemistry and were both so excited to be on set together every day. We both love show tunes, so there was never a quiet moment between the two of us on set. But I think what we loved most about working together was knowing how special and important this story is, and how lucky we were to get to be the ones to tell it. We would drive home from work each day on cloud nine, and George would just always say in the van, “We are so lucky.’’ It’s fun working with an actor who’s newer to the filmmaking scene; George reminded me every day of why I got into the business in the first place. We learned a lot from each other.

George wears Thom Browne suit, Gucci watch, and Prada loafers. Jonathan wears Thom Browne suit and tie, Gucci watch, and Gucci loafers.

Can you describe your transition from acting to producing? Was this something you always wanted to do?

I’ve always loved storytelling, but as an actor, you can only do so much, so producing has become second nature to me. I think if you ask anyone I’ve worked with, I basically have been producing for years whether I knew it or not. I’ve always been very vocal about my opinions in the filmmaking process, LOL. I always try to help advance the film and the process of filmmaking to make the best film possible; it’s just now that they’ve given me an actual title. Ha! Producing with Hallmark Channel is unlike any other experience in the industry. Hallmark treats their talent like a family, and really believes in the talent and their dreams and creative process.  Producing The Holiday Sitter with them has been such a creatively fulfilling process, and the network has been so caring in making sure we tell a truthful story of what LGBTQ+ love looks like on camera. And off-camera, we have such a diverse group of queer people leading the creative elements, from producing, to directing, to writing, that it’s a dream come true for so many talented queer artists telling this story together. 

How would you describe your style right now—are there any particular inspirations you’ve drawn from?

My style consists of whatever I borrow or “accidentally take home” from the wardrobe department on my movies because someone else that knows what they are doing picked it out for me. My style on the town is a mix of clothes from Express, because everything from Express looks good, so for someone like me who’s not good with fashion, I never have to think about it, I just know it’s gonna look good. If I’m not at an event or red carpet or on set, you’ll find me 100% of the time in gym clothes and Crocs. That’s where I feel my fashion really shines. Pajama adjacent at all times.

How do you take care of yourself when you’re not working?

I don’t know the last time I’ve had time off since I got married to my husband Jaymes in March. After our wedding, we launched OUTbound, our LGTBQ+ Travel company that does gay cruises around the world. Our 2022 season was such a success because of the support of the queer community. OUTbound traveled to Croatia, Portugal, Spain, Mexico, and we are headed to France, Germany, and Switzerland at the end of the year for our Christmas Markets Cruise. So between shooting Hallmark movies, OUTbound, and my iHeart Pridecast podcast, I honestly don’t have a day off, ever. But next time I do, I just want to do the normal things with my husband. Drink coffee in the backyard and throw the football for our Goldendoodle, Brad. That’s real life. That’s what I love most.

George wears Alexander McQueen shirt. Jonathan wears Alexander McQueen shirt.

Photographed by Noah Asanias

Styled by Sarah D'Arcey

Groomer: Katrina Wrobel

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Jonathan Bennett, George Krissa, Mean Girls, The Holiday Sitter, PRIDEcast, OUTbound, Jess Ferguson, Alexander McQueen, Sarai Bespoke, Thom Browne, Gucci, Prada, Noah Asanias, Sarah D'Arcey, Katrina Wrobel