New week, new episode! We’re catching up on a Christmas movie from 2025 that slipped through the cracks — and it’s a little messier than your typical Hallmark Christmas movie. Today, we're talking The Baltimorons.

A newly sober man’s Christmas Eve dental emergency leads to an unexpected romance with his older dentist as they explore Baltimore together.

September 5, 2025 | Theaters

• Michael Strassner as Cliff
• Liz Larsen as Didi

The movie kicks off with a drunk guy stumbling up to an attic. He’s clearly having a rough time.

Cut to Christmas Eve. Cliff tells his girlfriend, Brittany, that he’s six months sober. They arrive at her mom’s house, where Cliff immediately nails his mouth and loses a tooth. He has to drive around Baltimore looking for a dentist and eventually finds one. The bad news? He’s terrified of needles and passes out the second he sees one.

The dentist, Didi, is clearly going through it herself, but she helps him out and tells him he’ll need to come back on Monday to get the crown put in. When Cliff walks outside, he realizes his car has been towed. Didi sees him and offers to drive him to the tow lot. She’s very kind—but also clearly annoyed by Cliff, who is… a lot.

They get to the tow lot and find it closed. Once again, Didi helps him out. To thank her, Cliff insists on taking her out to dinner, assuming she has no plans since her kids are at her ex-husband’s house. Instead, she decides she wants to crash her ex-husband’s party—and wants Cliff to come with her. Cliff understands the assignment and does everything possible to make Didi look amazing while making her ex absolutely miserable.

They keep hanging out afterward, and Cliff opens up about his past in improv. Didi suggests they go to a show. Cliff admits he was fired because he “bullied” another comedian and hasn’t been back since. He really wants to go, but he’s nervous.

They go anyway, and his friend Marvin calls him up on stage. Cliff panics and says he can’t do it—but Didi pushes him to get up there. The crowd wants him to perform his Baltimorons sketch, but it needs a second person. Everyone gets awkward, so Didi volunteers.

It starts off rocky, but eventually improves, and they end up kissing on stage—until Cliff abruptly calls “end scene.” Didi is embarrassed and storms off. Cliff explains that he smelled alcohol on her breath and panicked because he’s six months sober. He didn’t think he could perform sober, but now he knows he can. He wants to keep the night going, especially since his fiancée is already mad at him.

They head to Didi’s boat and go out on the water. When they return to the dock, Brittany is waiting for him. She saw on the tracker app that he was in the middle of the water and got worried. They argue, and it seems like they break up.

Cliff goes back to Didi’s place. They slow dance. They kiss. What a night.

The next day, Cliff returns to his place, where Brittany shows up. They talk and officially break up, realizing it’s what’s best for both of them.

Cliff goes back to Didi’s house. She invites him in.

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It's finally happened. BRENDEN PENNY IS ON THE LINE!

Brendan Penn is a Canadian film and television actor who first became well known to TV audiences as A.J. Varland in the first season of Whistler that aired in Canada from 2006 to 2008. Brendan starred as Kevin O'Brien in the Hallmark Channel family drama series Chesapeake Shores & is now a Hallmark staple, appearing in many Hallmark Channel movies.

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Join us as we catch up on our mail from over the holiday season!

Watch the show on Youtube - www.deckthehallmark.com/youtube

Interested in advertising on the show? Email bran@deckthehallmark.com

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.