The Rookie characters have been through some pretty awful relationships over the show's five seasons, but five of them were more difficult to watch than others. From an unexpected couple in the pilot to a regretful hook-up later on in the series, the writers have never been afraid to pair up the LAPD officers with other characters that they had no business being with. But unfortunately for the audience, they're the ones who had to sit through all of these exasperating relationships.
The good news is that none of these pairings are still together. There's a reason why they didn't work out, and there's a reason why they induced secondhand embarrassment in the viewers. These couples weren't meant to be together, and they were just cringeworthy stopping points for the characters before they found their perfect matches in The Rookie.
5 Nolan and Lucy
John Nolan, Lucy Chen, and Jackson West met at the training academy prior to the pilot of The Rookie, and they were all assigned to the Mid-Wilshire station in Los Angeles. The three of them seemed like the best of friends. However, at the end of the series premiere, the show revealed that Nolan and Lucy's dynamic was a bit more romantic.
Nolan and Lucy were dating, but had to keep it a secret from their fellow officers, as they didn't want their colleagues to view them in a negative light because of their relationship. However, when Nolan's training officer Talia Bishop found out about the couple, she warned that their connection would mark Lucy for the rest of her career because of the unfair stigma put on woman cops who fraternize with male cops. Nolan and Lucy broke up early on in season 1, much to the delight of fans. There was no chemistry between the two, and their entire dynamic - given their age difference - left a poor taste in viewers' mouths.
4 Tim and Ashley
Tim Bradford and Ashley McGrady were one of the most difficult relationships to witness in The Rookie. They were obviously paired together to be a roadblock for Chenford, but it still made no sense for them to be together. They might have looked good together, but when they opened their mouths and communicated, it was awkward and cheesy.
Ashley was Tim's last relationship before he finally gave in to his feelings for Lucy, and viewers always knew their romance would end eventually. It was only a matter of time before they broke up, but the way they ended was a surprise, which made the couple even more frustrating. It might have been more believable had Ashley broken off their relationship because of Tim's obvious affection toward Lucy, or if Tim left Ashley because he wanted to explore something with Lucy. However, when Tim's bullet wound from season 1 forced him to get emergency surgery, Ashley realized she couldn't date a cop. Their unnecessary romance ended, and The Rookie was better off for it.
3 Lucy and Chris
Lucy's relationship with Chris Sanford paralleled Tim and Ashley's in The Rookie in the way that it was just something that got in the way of Chenford. Viewers knew that Tim and Lucy would eventually end up together, so Lucy and Chris never made sense, and it was easy to look away when they shared scenes. Their romance had an expiration date, and, thankfully, it came in The Rookie season 5.
However, even though Lucy and Chris weren't meant to be together, they also had a handful of downright cringy moments. No one could ever forget the scene when Chris subconsciously hummed "Dream A Little Dream Of Me" right in front of Lucy after watching the video of her in the barrel when Caleb Wright buried her alive. Plus, Chris was oblivious to Lucy's hesitation when it came to buying a house together. She wasn't ready to take the step while he was attending open houses. Ultimately, Lucy broke up with Chris to be with Tim in The Rookie season 5, episode 9, and it all worked out in the end.
2 Harper and Donovan
The Rookie characters aren't prone to making mistakes, and Nyla Harper made a big one in season 4 when she got drunk with her ex-husband, Donovan Town, and they slept together. Harper and Donovan previously had a tumultuous relationship that resulted in a tense custody battle for their daughter, Lila. Eventually, Donovan agreed to share custody, but that didn't mean that he and Harper should have reignited their spark. They weren't right together. Plus, Harper and Donovan were seeing other people when they slept together, making their hookup even more awkward.
When they woke up the morning after, the exes agreed that sleeping together was a slip-up and should never happen again. A few episodes later, Harper found out she was pregnant, but the show never dove deep into the "who's the father" storyline. They made it very clear that it was James Murray's baby, and Harper never thought twice about that. She never even told James about sleeping with Donovan, which adds another level of cringe to the whole situation. Thankfully, the unwarranted hookup, which never had any real consequences on the characters' storyline, is in the past, and Harper is very happy with James and their daughter, Leah, in The Rookie.
1 Jackson and Sterling
Jackson West didn't have many substantial relationships throughout his time in The Rookie, but his most serious one was probably with Sterling Freeman. The two met in season 2 when Jackson and Angela Lopez worked as police consultants on the set of a popular procedural television series. Jackson was a fan of the show, and when he met one of the stars (Sterling), they immediately hit it off.
For a while, Jackson and Sterling's romance was entertaining and sweet, but it took a cringeworthy turn when Jackson found out that Sterling lied to him about his past. He wasn't honest about his real name, where he came from, and his former criminal exploits. Sterling had assisted a cult leader in a robbery, which put a quick end to his and Jackson's relationship. Their breakup was rushed, and fans only found out about it via a true-crime documentary. Given the end of Jackson and Sterling's romance in The Rookie, it's difficult to look back on it as a whole without wincing.