While Shay was definitely one of the best characters, she did not have great taste in women. Devon took advantage of her and robbed her apartment, stealing money and collectibles from Shay, Severide, and Otis. Shay was already in a bad place, and she nearly became suicidal. It doesn't get much worse than that.

These two are going through a rough patch. Olinsky had an affair while undercover, resulting in a surprise daughter. While Meredith has every right to be angry, she is being completely unreasonable about Michelle, and she's unwilling to even talk about it. Instead, she threw Olinsky out, forcing him and Michelle to stay at Ruzek's small apartment. Hopefully these two will work it out, but for now, their drama puts them low on our list.

Harrison and Brett were engaged before Harrison broke it off, leading Brett to start over in Chicago. While he did return to apologize, it was clear this guy did not appreciate what he had, even going so far as to imply that Brett can't take care of herself without him. Well, she proved him wrong, and thankfully sent him back to Indiana...by himself.

It seems that at one time Antonio and his wife Laura had a great relationship, but the dangers of Antonio's job hit home for her when he was shot. They get in a fight when he returns to work early, leading Laura to pack up the kids and leave him devastated and alone.

Severide has not had the best of luck in the romance department. Jamie seemed promising at first, even earning the right to wear his hockey jersey. But, things went south fast when she agrees to represent the evil Maddox. Eventually she did come through and help him take him down, but any hope for their relationship was long gone.

We love Jimmy, but Chili is in the process of falling off the deep end. Her behavior has been erratic and irresponsible, and it has gotten both her and Jimmy in trouble. It may have been Casey who told Jimmy to break up with her, but until she gets some help managing her grief, it was the right decision. She's a mess.

Shay's pregnant ex strolls back into her life, and the two plan on raising the baby together. Shay helps Clarice fight for custody and makes plans to move in with her. Unfortunately, Clarice makes a deal to split custody with her ex-husband, but it requires her to move to New York. Poor Shay is left heartbroken for the second time by this girl!

Remember Ruzek's first, no wait, make that second fiance? The two seemed to have a pretty fun and playful relationship, but then sparks began to fly between him and Burgess. Wendy could see that something had changed with him, and she smartly ended the engagement.

Severide fell hard for Renee, and even strongly considered moving to Spain with her after she received a promotion. Ultimately, he realized he'd never be happy giving up his career, and the two broke up. That may not seem so bad, but she returned a few months later, telling him she was pregnant with his kid. Being the trusting guy that he is, he planned to raise the baby with her, until Shay helped him realize the timing was off. After a paternity test confirmed he's not the father, they broke up again, for good.

We know Zoya was with Severide first, but Cruz was the one she nearly married for a green card. Cruz's spontaneous proposal was not thought through. This relationship was doomed from the beginning, but luckily Zoya had the sense to break it off and move back to Russia before Cruz had a chance to make a huge mistake.

Call us crazy, but we were actually kind of rooting for this one. They were both in bad places in their lives, and not in the greatest state of mind when they decided to get married on a whim in Vegas, but, surprisingly, they were actually good for each other. The marriage was never meant to last, but they helped each other realize they were trying to escape their problems. Their split was amicable, and both were ready to start moving on with their lives.

Remember when Halstead and Dawson dated each other? Seems like a distant memory now, but at the time they were pretty hot and heavy. The relationship started out on a lie, and that usually spells doom. Halstead was undercover, and Dawson didn't even know he was a cop...or that he worked with her brother! They tried to keep the relationship going even after Dawson learned the truth, but when things got too dangerous, Dawson realized she couldn't date an undercover cop.

They didn't exactly get off on the right foot, with Mills accusing Isabella of using him as leverage to join a campaign, but she swore her intentions were innocent. With his help, the senator did offer her a job, and their short romance came to an end with a tearful goodbye.

Some of the best couples start out as friends, and Brett and Cruz got closer when she inadvertantly attended his zumba class. She then taught him how to cook, and their romance blossomed from there. These two were really cute while they lasted, but eventually Brett realized that even though she adored Cruz, they wanted different things. She planned to break up with him, but Cruz beat her to the punch, probably because he knew what was coming.

Mouch and Mari crack the top ten because they were simply adorable. It was mostly long distance, but she did inspire him to campaign for union president. He was understandably devastated when she eventually dumped him for a game show host, but long distance relationships are never easy!

Believe it or not, this was Severide's most stable relationship. It was also the first one to cross over the two shows. They really worked as a couple, and they certainly did not lack for chemistry. They had a lot in common, but ultimately, they were not meant to be. After Shay died, Severide became more detached, and Lindsay realized they were better off as friends.

Casey and Hallie were together for eight years, and even got engaged. They broke up after a disagreement over children, but ended up reconciling because they still loved and missed each other. Their romance came to a tragic end when Hallie was murdered, leaving Casey absolutely devastated.

Mills and Dawson were supposed to be the highest ranked couple no longer together, and for good reason. They oozed chemistry, and it was obvious they really cared about each other. Their relationship started in secret, and came to an end because Dawson kept one from him regarding his mother and Chief Boden. They might have been able to work it out, if it weren't for Dawson's growing feelings for Casey.

Ruzek and Burgess were one of the hardest couples to rank. They started out solid, full of sweet, romantic moments and amazing chemistry, especially when they were still keeping their relationship a secret. But, then Ruzek developed commitment-phobia, forcing Burgess to return his ring. Because of that, Mills and Dawson aren't the highest ranked broken up couple anymore. We're hoping they work it out, but until they do, this is as high as they go.

Boden nearly botched this one with his original proposal leaning more towards supporing her and the baby financially, rather than making it about love. Luckily, he got another chance, and these two have a solid marriage. They went through some tough times with their baby's delivery, and arguments about his name, but they worked through it. She supported him through his legal troubles, and we loved watching her stand up to Serena. These two are going to make it.

Herrmann and Cindy have the longest tenured relationshp and have five kids to show for it! A guy who surprises his wife on their anniversary with a vasectomy earns them a place in the top five. Add that to the support and love they've shown each other over the years, through near death experiences, a miscarriage, financial problems, and you know this is a solid couple.

These two danced around each other for awhile, trying to abide by Voight's rules. When they finally gave into their feelings, it could not have been hotter. Their chemistry was off the charts, but they broke it off due to Lindsay's reluctance to go public. It didn't stick though, and the two are not only back together, but out in the open. Here's hoping they're in it for the long haul this time!

Surprised to see them all the way at number two? What can we say, we adore this couple! They are super cute together, and Platt's re-proposal to Mouch was perfectly fitting. They're currently dealing with some money troubles, but we are confident they will figure it out. Their relationship is strong, and we expect their marriage to be a lasting one.

Did you expect anyone else to take the number one slot? These two have been through so much, including break-ups, a miscarriage, a kidnapping, and so much more, but their relationship has survived it all. No matter what drama the writers keep throwing at them, we know Casey and Dawson are end game.