Chicago Fire has 11 seasons worth of dramatic and exciting relationships,

but some have only brought pain to the characters and the fans who were

rooting for them. Viewers love a good romance, especially if it develops over

time and it makes sense for two people to be together. However, when watching Chicago Fire, fans know that relationships often come and go in the show, and sometimes, they end in tragic heartbreak.

The NBC series revolves around the firefighters and paramedics of Firehouse 51, and given that they risk their lives every day on the job, deaths are bound to happen. Or sometimes, characters unexpectedly leave the show, and their significant others are left to deal with their heartbreak. Chicago Fire season 11 might add another couple to this list if Taylor Kinney, who plays Kelly Severide, never returns, but that’s a problem for another day. Here are five previous Chicago Fire relationships that have ended in disaster.

5.Dawson and Casey

When Chicago Fire first premiered, everyone believed Matt Casey was engaged to Hallie Thomas, but it was obvious that Gabby Dawson had a crush on him. It would only be a matter of time before Dawson and Casey acted on their feelings for one another, but the writers made fans wait a long time before that happened. After Casey and Hallie officially broke up and Hallie later died in a fire, Dawson and Casey confronted the tension between them. Unfortunately, the fan-favorite couple would continue to be on and off for the majority of their time together in the series.

Dawson and Casey finally married in season 5 and tried to have a baby, but Monica Raymund, who played Dawson, decided to leave the series at the end of season 6. To explain her exit, Dawson left for Puerto Rico, and she and Casey subsequently got a divorce. It was an unfortunate ending for a relationship that Chicago Fire fans had been rooting for since the show’s pilot, and Casey later moved on with Dawson’s former partner.

4.Severide and Anna

Severide has had multiple romances and flings throughout Chicago Fire‘s 11 seasons, but the one that arguably changed him the most was his connection with Anna Turner. Anna was a leukemia patient waiting for a bone marrow transplant that would potentially save her life. Severide met Anna in season 5 after Jeff Clarke convinced the firefighter to donate his bone marrow to her. After the procedure, the two started dating.

Anna seemingly got better, and she and Severide had a whirlwind romance. Unfortunately, Anna’s leukemia had other plans for the two. Her health started deteriorating, and she decided to sign a DNR, which upset Severide since he was in love with her. Anna was admitted to the hospital, where she became septic and died. Severide sat at her bedside and pleaded for the doctors to help her, but there was nothing they could do. Severide and Anna had one of the most tragic love stories in Chicago Fire. Regardless, he became a better man for loving her.

3.Violet and Evan

Violet Mikami and Evan Hawkins’ relationship in Chicago Fire is another one that painfully ended in death. Evan was the Paramedic Field Chief, and he and Violet met when he rode along with him and Brett while he was considering approving Brett’s paramedicine program. Their romance developed from there, and they began dating later in season 10.

Despite some trouble due to others pointing out Evan’s favoritism toward Ambulance 61, Violet and Evan fell in love. Sadly, in season 11, Evan died during a fire call when a building collapsed on top of him while he was trying to save a victim. The whole scene happened right in front of Violet, and she tried to resuscitate him after the firefighters pulled the wreckage off of him. Violet’s efforts were fruitless, and she was left to mourn Evan in Chicago Fire.

2.Brett and Casey

On a lighter note, neither Brett nor Casey died in Chicago Fire, but circumstances beyond their control tore them apart in season 10. During the early part of the series, they were just friends since Casey was involved with Dawson and Brett was Dawson’s partner on Ambulance 61. However, that all changed once Dawson moved to Puerto Rico.

Brett and Casey gradually developed feelings for one another but took their time acting on them since they felt guilty about the Dawson situation. Eventually, they gave in to their obvious chemistry and started dating at the end of season 9. In season 10, Brett and Casey’s relationship was thriving, right up until the point when Casey decided to move to Oregon to become the guardian of Andrew Darden’s sons. He and Brett committed to trying a long-distance relationship, but Brett broke up with him in season 11 when the separation became too much. However, after Casey returned in Chicago Fire season 11, episode 18, there’s always the possibility that he and Brett will find their way back to one another. For now, their relationship has ended.

1.Otis and Lily

One of the most heartbreaking deaths in Chicago Fire was Otis’s, and it was made all the more tragic by the fact that he left his girlfriend, Lily, behind. Their relationship didn’t get much airtime on the show, but it was sweet, and viewers were happy to see Otis happy. Otis and Lily first met in season 6 when Otis, Gabby, and Christopher Herrmann bought Lily’s father’s bar and called it “Molly’s North.” Sparks immediately flew between the two, and before fans knew it, they were dating.

Unfortunately, Otis died during the season 8 premiere. The firefighters responded to a fire at a mattress factory, and when a boiler exploded, Otis risked his life to save everyone else’s. The first responders rushed Otis to a nearby hospital, where he eventually died from his injuries. The audience never got to see Lily’s reaction to Otis’s death, but she helped organize his memorial and undoubtedly mourned the loss of her boyfriend. Lily even closed Molly’s North in Chicago Fire because it was too painful to run given its connection to her late boyfriend.