16. Gabby Dawson and Peter Mills
Gabby Dawson always had a crush on Matt Casey. He was unattainable due to his relationship with Hallie Thomas, and then later, his drama with his mother made his life too complicated for a girlfriend. Gabby was never able to go after the man she wanted, so she set her sights elsewhere. Romance blossomed out of a friendship with Peter Mills (Charlie Barnett), but something never felt quite right about it.
Peter was never going to be Gabby’s number one, as Casey always held that spot. Gabby led Peter on for far too long, as she could never shake her feelings for the lieutenant. Gabby also finds out that Chief Boden (Eamonn Walker) had an affair with Mills’ mother and holds the secret for a while. When Mills finds out, they break up, which is probably the best thing that ever happened to him. He was also onto Gabby about having feelings for Casey, and this relationship just seemed like the second roadblock to Dawsey becoming a thing. Gabby and Mills actually become really great friends, and we wish they never dipped their toes into the romance pool.
15. Eric Woodruff and Daren Ritter
Darren Ritter (Daniel Kyri) is easily one of the most likable people on “Chicago Fire.” Introduced in Season 7, the candidate serves on Engine 51 and becomes close with Christopher Hermann (David Eigenberg) and Mouch McHolland (Christian Stolte). We met his boyfriend Eric Woodruff (Curtis Edward Jackson) in Season 8, but their relationship gets a stronger storyline in Season 9.
After quarantining together during the pandemic, Eric and Ritter broke up because they spent too much time together. Ritter went on a blind date with someone else, who also happened to date Eric. The blind date talked trash about Eric, which caused Ritter to defend him, and the exes rekindled their relationship. However, it came to an end for the second time in Season 10, when Eric realized he would never be able to understand Ritter’s place in the firefighting world. The duo came to the conclusion they wouldn’t be able to work, especially since Ritter loves his job as a firefighter too much.
14. Erin Lindsay and Kelly Severide
Severide and Erin Lindsay (Sophia Bush) are one of the many “One Chicago” crossover relationships. While it might be better to classify their relationship as a fling, there were some serious feelings between the two, and they were a duo that fans definitely had opinions on at the time. The “Chicago P.D.” star made her way into the “Fire” family in Season 2 when she investigated the kidnapping of Katie. She and Severide are attracted to one another immediately and share one of the steamiest kisses in “Chicago Fire” history.
However, the death of Shay brings their fling to an end as Kelly slips into a depression and stands up Lindsay on several occasions. She promises to always be there for him but says she is not a woman who will sit around and wait for him. Luckily, she moves on rather quickly to Jay Halstead (Jesse Lee Soffer), and they serve as one of the best couples ever on “Chicago P.D.”
13. Anna Turner and Kelly Severide
Anna Turner (Charlotte Sullivan) made her “Chicago Fire” debut in Season 5 for the series’ landmark 100th episode. Former 51 member Jeff Clarke (Jeff Hephner) suggests Severide get tested to see if he can donate bone marrow to Anna (who has leukemia), and he turns out to be a match. Severide and Anna go through with the procedure and start dating shortly after. Anna even moves to Chicago to be near Severide and takes a pediatric nurse position at Med.
They have a whirlwind romance, but it comes to an abrupt stop when Anna’s health starts deteriorating again. Tired of fighting her leukemia, she signs a DNR. This frustrates Severide, but he’s able to be by her side when she takes her last breath. The two made for a decent couple, but it never looked like Anna was going to be Severide’s forever. It was one of the softest we’ve ever seen Severide, and made him the more compassionate and loving person we know him as all these seasons later.
12. Katie Nolan and Otis Zvonecek
The first love interest we get to see for Brian “Otis” Zvonecek is Katie Nolan (Brittany Curran), the half-sister of Kelly Severide and daughter of Benny Severide (Treat Williams). The two tried to keep their affection from one another away from Kelly, who was overly protective of a half-sister he never knew existed. Otis and Katie only get to date for a few episodes, but we get to see how much he cares for her after Vince Keeler (Jacob Weary) kidnaps her as revenge against Kelly.
Otis visits Katie in the hospital after she’s rescued, but the two have to end their fling because she is too traumatized to stay in Chicago. She ends up moving to New York to accept a position in a restaurant (one she initially debated taking because of Otis), but she goes on to live a happy life in the Big Apple. She returns for Benny’s funeral in Season 7 and runs into Otis, and it’s obvious there are still sparks between the two, but he had moved on to someone else at this point. If Katie was never kidnapped, she very well might have lived a happy life with Otis — until his untimely death in Season 8, that is.
11. Brittany Baker and Kelly Severide
In Season 3, Kelly Severide shocked everyone at Firehouse 51 when he returned from Las Vegas a married man. Severide met Brittany Baker (Serinda Swan) while at a craps table, and the two instantly fell in love. Within 24 hours of knowing each other, they got married and were truly head over heels.
We later find out that Brittany was in Vegas to help get her mind off her sister’s death, while by pure coincidence Severide was on vacation to distract himself from Shay’s death. They were exactly what one another needed to get through very tough times. They eventually realized that their marriage just wasn’t going to work, since Brittany was homesick and wanted to return to Florida. No one did anything wrong; no one lied; no one was mean. It just wasn’t meant to be. They were a very fun couple to watch together, despite how short-lived their four-episode marriage was.
10. Sylvie Brett and Kyle Sheffield
The sparks are instant between Sylvie Brett and Kyle Sheffield (Teddy Sears) in Season 7. The new Chaplain for the CFD takes a liking to Brett instantly, but he ends up breaking her heart when he dumps her because of his job. Matt Casey makes an excellent point to the Chaplain — that it’s hard for people of the CFD to confide in him if he’s dating someone within the department. However, it’s not the end of their romance.
Kyle proposes to Sylvie in the Season 7 finale after he’s offered a position in Indiana, which will take him out of the CFD. Knowing how incredible she is, he wants her to come with him, and Sylvie somewhat hesitantly accepts the proposal. Around this time, something starts to brew between Casey and Brett, but she still accepts and leaves Chicago. In the Season 8 premiere, she tells Kyle she can’t be with him and misses 51 too much. She moves back to Chicago and back into Casey’s life.
Brett and Kyle made a really great couple, and there was nothing wrong with their chemistry or relationship. They were just two wonderful people who wanted different things.
9. Lily and Otis Zvonecek
In Season 6, Lily (Ariane Rinehart) is introduced as the daughter of a bar owner who recently had to close down his business. When Otis goes in to see if he can buy any used equipment for Molly’s, he meets Lily, and there is a spark immediately between the two. Otis is smitten with Lily, and the feeling is mutual. He goes from looking for some cheap equipment to buying the bar, and he convinces Hermann and Dawson to hop on board. Lily’s family bar is now known as Molly’s North, thanks to Otis.
Lily is also a tremendous support for Otis after his neck injury in Season 6, and sticks by him in the hospital and during his grueling physical therapy. This is Otis’s second and last relationship on the show, but he definitely has one of the healthiest love lives out of any “Chicago Fire” character. We don’t get to see Lily’s reaction to losing Otis in the Season 8 opener, but we find out that she chose to close down Molly’s North, as it was too much of a reminder of her fallen beau.
