For fans of Chicago Fire, Firehouse 51 is more than just a fictional battleground for bravery—it’s a second home. We’ve followed these firefighters and paramedics through triumphs, tragedies, and everything in between. But not every moment has aged like a fine wine. While the show delivers powerful drama and emotionally charged storylines, there are a few scenes that made even the most devoted Chi-Hards squirm in their seats.
Whether it was a poorly executed romantic subplot, an awkward encounter, or just plain over-the-top writing, these scenes made us cringe—sometimes unintentionally, sometimes by design. Let’s revisit ten moments that left fans either laughing nervously or hiding behind their hands.
1. Boden Walks In On Otis & Katie (Season 2, Episode 13)
During a power outage that forced locals to take shelter at Firehouse 51, Otis and Katie decided to sneak off for some alone time—in the shower, of all places. Just as things heat up, they’re caught by none other than Chief Boden. Cue the red faces and secondhand embarrassment. Seeing Otis—usually the comic relief—caught in such an awkward moment was uncomfortable, especially since Boden is, well… Boden.
2. Shay’s “Plan B” Baby Idea (Season 1, Episode 19)
When Shay asked Severide to be her donor, things got weird—fast. After discovering she couldn’t afford artificial insemination, she jokingly suggested a more “hands-on” method. Her graphic description and the use of the word “mounted” left both Severide and the audience deeply uncomfortable. Thank goodness they moved past that plan.
3. Casey’s Dirty Laundry Gets Aired (Season 3, Episode 15)
Dawson and Casey’s relationship had its ups and downs, but nothing was as awkward as when Chief Welch dropped the bomb about Casey hooking up with his superior’s ex-wife. The reveal, which should’ve come from Casey himself, felt like a soap opera twist—and not the good kind. Watching Dawson’s reaction was like watching a car crash in slow motion.
4. Brett & Antonio’s Cringe-Flirt (Season 5, Episode 1)
Chemistry is important in any romance—but not every spark ignites. When Brett and Antonio’s flirtation began, fans were hopeful. That changed the moment Brett called herself a “regular David Copperfield” and Antonio responded with a “magic hands” line that landed with a thud. The dialogue felt painfully scripted, and even Gabby looked like she wanted to disappear.
5. Cruz’s Desperate Proposal to Zoya (Season 2, Episode 8)
Joe Cruz is a fan-favorite now, but back in Season 2, he made some questionable choices—including proposing to Otis’ cousin Zoya so she could get a green card. Not only was this wildly out of character, but it also came off as desperate and poorly thought-out. Thankfully, that storyline was short-lived and he eventually found his match in Chloe.
6. Shay, Dawson, And The Leather Harness (Season 2, Episode 10)
The paramedics have seen it all—but this one really took the cake. Responding to a call involving a man stuck in a leather harness after a romantic misadventure, Shay and Dawson showed restraint. Viewers, however, were squirming. The moment the man sniffed Dawson’s hair while half-naked? Absolutely not.
7. Protesters Hijack The Firehouse (Season 8, Episode 19)
While Chicago Fire has tackled social issues before, the episode where protesters chained themselves to trucks at 51 felt forced. Their cause—reopening a firehouse—was admirable, but the decision to stage a sit-in at a different firehouse confused viewers. The cringey community video montage at the end only made matters worse.
8. Jimmy’s Downfall (Season 5, Episode 2)
When Jimmy disobeyed Chief Boden’s orders in a fit of grief and anger over his brother’s death, it was more frustrating than tragic. His reckless move led to serious injury, and while the moment was meant to be emotional, fans couldn’t help but feel that he brought it on himself. What should’ve been a powerful arc was diluted by poor decision-making.
9. Severide’s “I’m Not Monogamous” Exit (Season 5, Episode 1)
Kidd offered Severide a place to crash. Instead of accepting the kindness or at least being honest, he panicked—blurting out that he “isn’t good with monogamy.” The implication? That their night together meant nothing. Fans weren’t the only ones wincing—Cruz, of all people, had to point out how terribly Severide handled the situation.
10. Casey’s Christmas Cheek Kiss (Season 1, Episode 10)
Dawsey fans have never recovered from this one. After finally agreeing to attend a Christmas party with Dawson, Casey almost reciprocated her affection—only to pivot last-second and kiss her on the cheek. Dawson’s reaction was to storm off, and while Casey’s intentions were likely pure (she was tipsy, after all), the result was heartbreakingly awkward.
The Bottom Line
Even the best shows have their off days, and Chicago Fire is no exception. For every emotional rescue and romantic spark, there’s a moment that makes fans collectively facepalm. But hey—that’s part of the charm. The missteps, cringe and all, are what make these characters feel real. Because sometimes, the most awkward moments are the ones we can’t stop talking about.
