Chloe Sullivan was in an on-and-off relationship with Jimmy Olsen from Season Six to Season Eight. They were about to be married when Davis Bloome arrived in Season Eight and fell in love with Chloe, resulting in a love triangle.
Chloe and Jimmy met during the summer of 2002 during an internship at the Daily Planet. Chloe lost her virginity to him but he never called her back causing her to put that relationship in the back of her mind. During season 4 while Lana was asking her advice about sex, Chloe revealed her summer romance and that she regretted her first time with Jimmy (whom was presumably Jimmy Olsen).
Chloe calls it "a summer infatuation that just was not special." In season 6 they accidentally met again where Chloe accidentally shot him due to the trauma of Dark Thursday. Chloe and Jimmy's relationship have been on and off due to Chloe protecting Clark's secret and Jimmy's inconsistency in how he feels about Chloe due to him constantly making up and breaking up with her.
He even dumps Chloe for Kara and then dumps Kara because she has amnesia. One of their major breakups was due to the fact that Jimmy had no kind feelings towards meteor freaks after being hurt by them and this prevents Chloe from opening up to him about her special abilities. Jimmy, due to having worked with Lex Luthor, accidentally got Chloe arrested by the Department of Domestic Security which turned out to really be one of Lex's projects at Black Creek pretending to be the D.D.S. However he does not admit the part that he played in her arrest even though it was not intentional. Jimmy also proposed to Chloe, realizing that he wants to be with her.
Chloe met Davis after a bus exploded and they both came to a young homeless girl's aid. There was an instant connection between the two and while both worked together to help Bette get settled, they quickly developed a friendship. Chloe was clearly impressed with Davis' kindness to help Bette and felt so comfortable around him that she told him that she was engaged to Jimmy before telling anyone else. Even Chloe was surprised how open she was around Davis.
Jimmy met Davis through Chloe and sought Davis out after he thought he could help him with the story of the attack on the Ace of Clubs and the serial killer. Jimmy asked if he could ride along with Davis in his ambulance to be the first on the scene if there was another incident. Davis was reluctant at first, as he suspected that he himself may be the killer. However, Jimmy was insistent and was keen to make friends with one of Chloe's friends. He managed to convince Davis by asking him to do it for Chloe. Before Jimmy and Davis left the hospital, Davis went to try to confirm his suspicions that he was the killer. Chloe walked in on him collecting DNA evidence from the latest victim and Davis revealed his secret, telling her he has been blacking out and waking up covered in someone else's blood. Clearly upset that he could be a murderer, Chloe refused to believe that he was the killer and insisted that he was innocent. Davis was surprised at her faith in him, but pleased that they had become so close so quickly.
Davis' feelings for her were growing stronger and when Chloe realised this, out of loyalty to Jimmy, she decided that she and Davis shouldn't see each other for a while. This didn't stop Davis' persistence, as he went to the Talon with a letter to try to convince Chloe not to marry Jimmy. However, to his surprise, he was met by Jimmy instead. As a cover, Davis told Jimmy that he was replying to his wedding invitation and would not be able to attend. Oblivious to Davis' growing feelings for Chloe, Jimmy remained friendly with Davis and was disappointed that he couldn't make it to the wedding, as he felt Chloe would want him there. He assumed the letter was Davis' RSVP but when Jimmy tried to take it, Davis pushed it into his pocket. Clearly feeling awkward to get in the middle of Chloe and Jimmy's relationship, Davis seemed to make a decision to leave Chloe alone. However, when Brainiac started to remove all her memories except those of Davis, she went to him for help. Deciding that she was better off to stay with Jimmy when she was in such a state, he returned her to the Talon. When she began to act fearful of Jimmy, Davis sedated her. Clark was then able to save her by Jor-El restoring her memories.
After her recovery, Davis approached Chloe in the alley behind the Talon. Chloe thanked him for his help and Davis confessed his love and refused to let her marry the wrong man. He then kissed her to Chloe's shock. She insisted that she loves Jimmy and said that the connection between her and Davis was never romantic but Davis showed no sign of giving up.
Chloe nervously prepared for her wedding with Davis still in the back of her mind. While she was getting ready, Davis continually phoned her and left voice-mail messages. Her loyalty to Jimmy prevented her from responding. However, Davis was calling Chloe for help as the beast inside him was becoming stronger. During Chloe's wedding, Davis transformed into Doomsday. Clearly still influnced by Davis' love for Chloe, Doomsday crashed the wedding. Jimmy tried to protect his bride but Doomsday seriously wounded him before kidnapping Chloe and taking her to the Fortress of Solitude.
At the Fortress, Brainiac possessed Chloe once again and revealed to Davis that the only reason why they were brought together was due to a program that he was running in Chloe's head. Davis is clearly confused and disturbed by this. Once Chloe is exorcised of Brainiac, she forgot everything that happened after Doomsday's attack. She didn't see Davis for a month as she prioritised Jimmy's recovery. She was very conscientious in caring for Jimmy, travelling between Smallville and Star City. Eventually, Jimmy was transferred to Metropolis General Hospital. His experience with Doomsday had clearly left psychological scars as well as physical wounds, as Jimmy was still having traumatic nightmares about Doomsday's attack. When he woke up he saw Davis murdering a man in the elevator.
Jimmy was shocked that Davis could be a killer and confided in Chloe. Their conversation was interrupted by Davis, who had been interviewed by police about Jimmy's claims. Davis was angry at Jimmy and tried to convince both Jimmy and Chloe that Jimmy's medication pump was faulty and had been giving him double doses, which caused him to hallucinate. Chloe was initially skeptical as she had previously seen Jimmy try to up his pain medication but the machine wouldn't let him. Davis insisted that the doctors and nurses can verify that the machine was indeed faulty and leaves. Having second thoughts, Chloe followed him out to apologize for Jimmy. Davis accused Jimmy of targeting him because of the kiss that they shared before the wedding. However, Chloe admitted that she had never told Jimmy about that. Davis was surprised by this but clearly encouraged, thinking that he might still have a chance with Chloe. However, he disguised his feelings and insisted that they would remain friends. Chloe then confided in Davis that she felt guilty for Jimmy's problems, suspecting that he would be better off without her. Davis gave her a comforting hug, which Jimmy saw through the blinds and was angered by this.
Eager to prove Davis' guilt and put a stop to Chloe and Davis' growing relationship, Jimmy sneaked out of the hospital to look through Davis' ambulance. He found the body of the man in the elevator stashed in the back. The shock caused him to jump back and cut his hand on some glass. When Davis discovered Jimmy in the ambulance, Davis tried to remain calm and accused Jimmy of trying to steal pain medication. Jimmy denied this and revealed that he had found the dead body. Davis decided to admit this to Jimmy but insisted that the driver was guilty of killing innocent people and so deserved to die. He then injected Jimmy with a sedative to knock him out.
Jimmy woke up in his hospital bed, hearing Chloe screaming his name. He found her running for her life and then locked herself in an exam room unaware that Doomsday was also in there. As Doomsday kills her, Jimmy watches in horror with doctors and nurses trying to calm him down. When Chloe arrived on the scene and Jimmy sees her unharmed, he realised that he had been hallucinating. This confirmed Chloe's suspicions that Jimmy was wrong about Davis and even made Jimmy doubt himself until he saw the cut on his hand from the ambulance.
Jimmy's hatred for Davis grew to the point where he was desperate to prove that he was right. He followed Davis to an alleyway where he was watching a thug break into a building. Jimmy knocked Davis across the head with a pipe to knock him out long enough to handcuff him to a chain-link fence. Jimmy confronted him and revealed that he knew he wasn't hallucinating. Suspecting that Davis was trying to steal Chloe away from him, Jimmy told Davis that he had called Chloe and wanted him to confess to her. This angered Davis, who then began to transform. Surprisingly not resentful of Jimmy, he warned Jimmy to leave, as he didn't want to hurt him. He then broke one of the handcuffs, which makes Jimmy nervous of Davis and he prepares to hit him again just as Chloe arrives and tasers Jimmy unconscious. His back turned, Davis continued to transform, warning Chloe to get away. Feeling guilty about what her husband had done to Davis, she touches his shoulder to check he is ok. Chloe's touch inexplicably reverses Davis' metamorphosis much to his delight.
Following this, Jimmy was furious with Chloe. However, she was still dedicated to helping Jimmy's recovery and got detailed instructions from the discharge nurse about how to manage his pain medication. Jimmy snatched them out of her hand and, although Chloe tried to remind him that he isn't alone, Jimmy insisted that he didn't need a wife that would rather trust her friends. Jimmy was clearly devastated that she had taken Davis' side over what he saw, after years of playing second fiddle to Clark. Chloe asked to continue the conversation at home but Jimmy made it clear that they no longer had a home together. He told her marrying her was the biggest mistake of his life and stormed out. Chloe was left alone in tears.
Keen to get revenge on Davis, Jimmy barged into Tess Mercer's office at the Daily Planet to leave a note telling her to "meet Davis Bloome", hoping that she would expose his guilt in the paper. Meanwhile, Davis' became obsessed with Chloe, now that he knew she was the key to controlling the beast. With Jimmy out of the picture, he stayed outside the Talon in the rain looking up at Chloe's apartment window longingly.
Having lost Jimmy, Chloe started spending more time with Davis. She admitted to him that Jimmy would not return her calls or messages. Davis sympathised with her but was pleased to be able to spend more time with her. Soon afterwards, Chloe discovered his secret. Initially, she was scared of him but Davis begged her to help kill him with the use of Dr. Groll's kryptonite cage. She reluctantly agreed and was visibly traumatised by watching Davis die.
However, he was soon resurrected and relied on Chloe to help calm the beast inside him. Knowing this was the only way to stop him, she agreed to keep him in the basement without telling anyone else.
This situation, soon put Jimmy in danger when he broke in to Chloe's apartment looking for money for drugs. Despite, their marriage breaking down, Jimmy still relied on Chloe. Oliver Queen discovered Jimmy there and then they were both attacked by Davis and held hostage in the basement. Davis phoned Chloe to tell her what happened and she was very concerned for Jimmy's safety. Still angry with Davis for making Chloe believe he was crazy, Jimmy began to taunt him. Oliver warned Jimmy that Davis was the monster that crashed his wedding, which made Jimmy more angry as it became apparent to him that Davis had been planning to steal Chloe from him from the beginning. He told Davis that he had taken everything else in his life so he might as well kill him. As Jimmy continued to provoke Davis, Davis' eyes turned red and he started to almost crush Jimmy's skull. Oliver quickly reminded him that Chloe would never forgive him if he hurt Jimmy so he let him go. Instead, he knocked Jimmy unconscious. Clark arrived just in time to prevent Davis from killing Oliver and dragged him to the Fortress of Solitude.
When Chloe arrived she found Jimmy being taken away by paramedics. Jimmy was clearly disappointed that she had been protecting such a monster and warned her to stay away from Davis. Nevertheless, Chloe made her way up to the Fortress to stop Clark from sending Davis to the Phantom Zone. Still believing in the good side of Davis, they went on the run.
Jimmy obviously still cared for Chloe as he helped track her down. After he discovered Clark's secret, he was then able to understand Chloe's decisions and, once Clark found them and exorcised Davis from his Doomsday persona, the couple reconciled. However, as Davis overheard this discussion he went into a murderous rage and impaled Jimmy on a pole. Having always believed in the good in Davis, Chloe was shocked that he would do something like this. Before he died, Jimmy saved Chloe from Davis, impaling him on a spike. Davis seemed at peace with the fact that he was about to die while Jimmy passed away in Chloe's arms. Devastated, Chloe burst into tears and regretted the decisions that led her here.