- "I've never loved anyone the way I've loved you - and I never will again. You will always be my brightest star, my knight in shining leather, my hero." - Chloe's letter to Oliver, Shield
Chloe Sullivan and Oliver Queen's relationship has evolved over the years, due to Chloe's role in helping coordinate missions for their team of heroes. They were at odds over the events leading up to the capture and murder of Davis Bloome, but have since repaired the friendship and have grown closer in season nine. Their friendship intensified and they fell deeply in love. After being in a relationship for over a year, they finally married in Season Ten.
Chloe and Oliver's relationship has been nicknamed "Chlollie" by fans 
Chloe first came into contact with Oliver Queen through her intrigue about Green Arrow. She first met Oliver when he became friends with Clark, although Clark had agreed to keep Oliver's identity secret even from Chloe. Chloe ultimately surmised that Oliver was Green Arrow by herself and admired his heroic work.
Chloe clearly thought that Oliver was good looking  when they first met and she was impressed with him after hearing Lois describe him and then meeting him in person. However, her opinion of him lowered when she discovered that he was taking drugs. When Oliver quit the drugs and apologized for his behavior, Chloe was happy for him to date her cousin, Lois Lane and was pleased that he made Lois so happy. Oliver and Chloe shared Thanksgiving dinner with Lois, Clark, Martha Kent and Lionel Luthor at the Kent Farm.
Oliver's relationships with Lois and Clark helped Chloe to put her trust in him when Clark got into trouble while rescuing Bart Allen from a LuthorCorp facility. Oliver immediately put his trust in Chloe and made her a 'Watchtower' for his team in order to save Clark and Bart. After the mission was a success, Chloe admitted that she truly admired Oliver and his super-powered friends, which was the start of a long friendship between Chloe and Oliver.
Chloe relied on Oliver's help when she needed a safe place for her mother, Moira Sullivan, to hide from Lex Luthor. Their dislike for Lex is something that Chloe and Oliver had in common and while Oliver was happy to help Chloe, his efforts to arrange a place for her mother to stay in Star City were wasted, as Moira slipped into a catatonic state and was forced to go back into care.
- "Work with Oliver is... exciting." - Chloe to Clark, (Siren)
During Oliver's time away from Smallville, he and Chloe remained in contact and Chloe joined Oliver's team of heroes independently of Clark on a part-time basis. Their relationship had progressed a lot during this time, as they had built up a strong level of trust between each other. Oliver was protective of Chloe, even though he put her in a dangerous situation when she was intercepting one of Lex Luthor's files and was confronted by a mysterious blonde woman, who attacked her with daggers. Chloe relied on Oliver's help to escape and despite the danger she had been in, she admitted to Clark that she found her involvement with Oliver exciting, although she admitted that her increased relationship with Oliver came about through needing the money. Oliver was defensive about using Chloe in his team when Clark criticized him for putting her in danger, as he clearly valued her help.
Oliver's resources came in handy again when Chloe needed to help Clark track down Lex. Clark sped to confront Lex but was incapacitated by Edward Teague, who intended to sacrifice him to fulfill the "Traveler" prophesy. She used a Queen Industries jet to get to Clark and save him.
- "Do I tell you how to shoot your arrows? I don't think so." - Chloe Sullivan to Oliver Queen, (Bloodline)
Oliver came to Chloe's aid again when she was seemingly arrested by the Department of Domestic Security. Oliver had been trying to get her released for some time before he discovered that the DDS had never arrested her. Once he found Clark, they teamed up to find Chloe and surmised that Lex had kidnapped her and they eventually tracked her down to Black Creek, where they rescued her.
Chloe returned the favor to Oliver when he was poisoned and collapsed at the Ace of Clubs. When he insisted that she and Clark don't take him to the hospital, Chloe assured Clark that Oliver must have a good reason for this, indicating the level of faith that she had in him. She respected his wishes and instead, took him to the Isis Foundation and brought Davis Bloome to help him. She was clearly very concerned for her friend as she stayed by his side and did everything she could to save him, including using her new power that she had acquired from Brainiac to research the poison. This information ultimately helped save Oliver.
After this, Chloe and Oliver had little contact for a while, as he went down a darker path of self-pity, after he was forced to give up his Green Arrow persona when his identity was compromised. When Clark convinced him to disguise himself as the red-blue blur in order to help protect Clark's identity, Oliver worked with Chloe to accomplish Clark's plan, which helped Oliver reconnect with his heroic persona. Chloe was then able to rely on Oliver's help when Clark and Lois went missing.
Oliver was reluctant to help Chloe and he was concerned by her involvement in Clark's dangerous life. Chloe insisted that she knew what she was doing and eventually convinced Oliver to help by stealing a generator from Tess Mercer. However, he was forced to rethink this when Chloe's eyes glazed over and her nose started to bleed, as she controlled the generator. Oliver was clearly concerned for her safety, but she pushed him into the next room. He later went to Clark to tell him about Chloe and was angry to discover that Clark was not doing anything about it. Oliver told Clark that he thought Chloe, as a human, was in over her head dealing with Clark's Kryptonian heritage.
Oliver prioritized tracking down Lex over Chloe's wedding to Jimmy Olsen and expected Clark to do the same, but he refused. Nevertheless, he showed deep concern when the wedding was crashed by Doomsday, who kidnapped Chloe. Oliver then tried to track down the creature. When Oliver later discovered that Chloe had come up with her own controversial method of combating Doomsday, he was not impressed.
Chloe and Oliver's friendship began to dissolve when they began to disagree on each other's choices of how to be a hero. When Oliver was injured in a bombing at LuthorCorp, he asked Chloe to help him track down the person he thought was responsible, which could lead him to Lex Luthor. Chloe was reluctant, but Oliver convinced her to comply by pointing out that if Clark went after Lex, he wouldn't finish him off and might even be in danger since Lex now knew Clark's weakness. Chloe tracked down Winslow Schott but ultimately gave the information to Clark anyway. She was appalled that Oliver had resorted to murder to deal with Lex. She told him she was going to tell Clark what he had done and Oliver shamed her into silence by questioning her role in the murder of Sebastian Kane, although she insisted that was Brainiac's doing.Despite these disagreements, Oliver attended Chloe's birthday party. She confided in him that she was not happy with her life and helped her make the decision to come on board with the Justice League full-time. On the surface, they seemingly put their differences behind them. However, Chloe clearly had not forgiven his murder of Lex, as she used it to convince Dr. Emil Hamilton into helping her find a cure for Davis. She told Dr. Hamilton that she went to him for help because Oliver could not be trusted.
When Oliver discovered that Chloe was keeping Davis in her basement, despite knowing that he was the serial killing monster, he was angry that Chloe was putting others in danger. Chloe insisted that she had the situation under control, as being near Davis calmed the beast. Despite having a once trusting relationship, Oliver clearly felt that Chloe had broken this trust through these actions and he remained skeptical of her defense. After this, Oliver was prepared to believe the worst of Chloe, as he believed that she had run away with Davis because she loved him.
Oliver went against the plans of Clark and Chloe by ordering the teammates to go against both of them. They tracked down Chloe and Davis and forcefully returned them to Metropolis. He restrained Chloe and prepared to kill Davis. Chloe fought back and used black kryptonite on Davis to separate him from the beast. Once Doomsday went on the rampage, he realized that he was not equipped with handling the situation and admitted his mistake in not trusting Chloe or Clark. He attended the funeral of Jimmy Olsen, who had been killed in the fray, but he stood apart from the team and Chloe only gave him strong looks of contempt. Nevertheless, she seemed concerned when she told Clark that Oliver and the rest of the team had disappeared.
- "And sometimes it's right in front of your face. You just have to want to see it." - Oliver Queen to Chloe Sullivan, (Warrior)
Chloe tried to reorganize the Justice League but her most difficult challenge was finding the whereabouts of Oliver and bringing him back. Because of his downward spiral, Oliver had lost the will to live and then Chloe, after placing a camera to spy and watch him for several weeks, devised a plan to make him rethink his life. With the help of her teammates, Chloe pushed Oliver over the edge to face his demons and find himself again and Oliver congratulated and thanked her for saving his life.
Oliver and Chloe continued to work together, becoming each other's partners, on missions including tracking down the Justice Society. Hawkman told Oliver that he pushed people away because he was scared. Oliver decided to remedy that by taking Chloe and John to dinner.
Chloe found Oliver at the Watchtower, doing some target practice, as well as they commiserated about the fact that neither of them has much fun these days. Oliver told Chloe that "Sometimes, you've gotta take your fun where you can get it. And sometimes, it's right in front of your face. You just have to want to see it." Oliver then showed Chloe how to shoot his bow and when she asked when she knew when to let go, he told her "It's all about your heart. Just listen. Right there, in between the beats. That's when you let go." Chloe kept looking at the hand he placed over hers and her expression implied she had just realized something.
A romantic relationship between Oliver and Chloe quickly developed, although their trust was temporarily disrupted when he discovered that she was embezzling money from his company. She quickly defended her actions by showing the arsenal of kryptonite weaponry that she had bought with his money.
Later, they checked in at a bed-and-breakfast together. When they ran into Lois and Clark, Chloe claimed that they're not a couple. They were just having fun and that she wanted their relationship to be without gifts and flowers, pressure and strings. Clark was concerned by the new relationship and asked Oliver not to take Chloe for granted.
Later Chloe and Oliver started to kiss when Chloe saw a gift from Oliver. She asked him if Clark talked to him, she then started to become upset and left their bedroom. Soon afterwards, Chloe was possessed by the Silver Banshee and went to take a shower with Clark. She fainted when the Banshee released her and was shocked when she realized where she was and that both she and Clark were naked. Recovering from the Silver Banshee's intervention, Chloe eventually got around to opening Oliver's gift, which was revealed to be a spoon. Oliver then jokingly got jealous when he mentioned to Chloe that the next time she wants to take a shower with someone, she should ask him. Chloe reassured him that, although she once loved Clark, he never did see that, didn't 'get her' and her wounds from that healed a long time ago. She then asked Oliver about Lois and he said that the scars are alway there but that doesn't mean they haven't healed. With their past relationships with Clark and Lois clearly behind them, Chloe and Oliver made a big step towards moving on and passionately kissed.
When Oliver was captured by Tess and other Checkmate agents as a part of a plot to get Watchtower, Chloe panicked and she worked with Clark to save him. However, Oliver was able to escape by himself and when he arrived at Watchtower, Chloe ran to embrace him in relief and they shared a sweet reunion with Clark looking on. Chloe and Oliver decided that it was best for him to lay low while Chloe investigated. Before she left, a slightly vulnerable Oliver asked her to be careful but Chloe was kidnapped. Oliver and Clark then worked together to save Chloe. Oliver expressed concern for Chloe stating that she scared the life out of him to which she replied, "You better be careful, Ollie. Or I might start to think you're falling for me." They exchanged smiles as she held his hand, the intimacy of their conversation showing that their relationship was becoming more serious. Even when Oliver was away on business, he sent Chloe a text message to say how much he missed her.
When Chloe and Tess become trapped in Watchtower, the two started talking about their common ground, Oliver. Chloe confessed that she lost her faith in people a long time ago and Tess assumed that’s the reason she won’t let Oliver get too close to her. Chloe responded by saying that it is the reason why she won’t blame Oliver when he leaves her. However, Tess reassured Chloe that her relationship with Oliver gave his life purpose. While Chloe was trapped, Oliver confronted Zod and got badly burnt by his heat vision. Once Chloe escaped she went to Met Gen to be with Oliver during his recovery.
Chloe eventually said to Clark that now she had Oliver in her life, she wanted to be plugged again into the real world.
Informing Oliver what was going on, Chloe was discussing the Kandorians and the impending war with him via web-cam. Oliver said that he was coming back to be with Chloe and feeling a declaration of love coming, she interjected, saying that he was coming because they needed to protect the database, awkwardly ending the conversation. Later in Watchtower Chloe was frantic as she tried to recover communications since Zod's soldiers had destroyed all of Earth's satellites. Oliver told her to calm down, that she had him, they were a team and she could trust him, then proceeded to mention that after Tess infiltrated Watchtower he had a satellite launched specifically for Watchtower, as a sort of gift to her. Chloe was excited and joked that she was planning to buy him a sweater as a birthday gift, but now she didn't know if that compared to a satellite. She was relieved, but Oliver told her he had to turn it on from the Earth station. Because she felt that Zod would be watching for any new satellite activity, Chloe gave him a hand radio and asked him to keep a low profile. Oliver suddenly kissed her and left to complete his mission, smiling and saying that since he was wearing his green leather, he would do his best, which left her smiling.
Chloe and Oliver eventually confessed their love for each other when Oliver was being attacked by a mystery attacker while he was in the air ducts of the Earth Station.
- "[..] I never loved anyone the way I've loved you. And I never will again. You will always be my brightest star, my knight in shining leather, my hero." - Chloe Sullivan's letter to Oliver Queen. (Shield)
After Oliver was abducted, Chloe went to the Justice Society of America's headquarters and put on Dr. Fate's helmet in order to find out where he was. When Clark asked her what she saw, she didn't mention anything about Oliver or trading herself for him. As Oliver was being released, he and Chloe bumped into each other. Once Oliver got into the car, he looked fearful, as though he realized something wasn't right. From the opposite car, Chloe was revealed to have gone through with the trade, showing that Oliver's safety meant more than her own life.
Oliver was at Watchtower, desperately trying to look for Chloe, when Tess showed up and informed Oliver that she had gotten his message and didn't understand what happened to Chloe. Oliver professed that Chloe was gone and he'd do anything he could to find the woman he loved. She remarked that Clark tended to do the same thing for Lois, but Oliver stated that they both of course knew where Lois was, but Chloe had disappeared. Tess suggested that Chloe possibly erased her own "existence" records. Oliver believed that possibility was very unlikely and handed Tess a printed e-mail that she supposedly sent him. Tess read the e-mail and it revealed much affection, passion, as well as devotion for Oliver. Tess denied posting such an e-mail and pointed out that they "both know" Chloe did. Tess admitted that she helped Chloe with "erasing" herself, trusting that she had a plan. Oliver went to Chloe's apartment looking for clues and found a photo taken by him with Chloe only on sheets on bed and a little bottle behind the photo. Oliver tracked down where he had been held captive and confronted Rick Flag, who told him that Chloe had traded herself for him and then "killed herself" to protect him. Oliver realized that Chloe had faked her own death after finding that the small bottle from the apartment contained an antidote to the cyanide pill. He felt guilty about Chloe's decision, blaming himself for it.
Oliver was training in his office at LuthorCorp, remembering the first kiss he and Chloe shared, when Lois interrupted and warned Oliver that Gordon Godfrey had obtained evidence about his secret identity as Green Arrow and was about to publish it in his new book. Oliver went to the church with his parents' photograph and he talked about what they taught to him when he was a child. He confessed that he tried and then said to his parents photograph that Chloe, the woman that he loved, sacrificed everything to protect him. Oliver started to think about his life and realized that Chloe sacrificed everything to protect him and his fellow heroes due to their secret identities. Lois, believing that Chloe was taking a vacation, said to Oliver that she knew what he meant to Chloe and she knew she would be back. He then made the decision to reveal his identity to the Earth so that Chloe could return to him and called a press conference to announce he was Green Arrow.
Meanwhile, at LuthorCorp, Oliver prepared for an interview with the local TV-media to discuss his alter-ego. Clark, however, entered the room, offering Oliver his silent support. Strengthened by Clark's presence, Oliver admitted that he recently lost Chloe. "I lost someone. She meant everything to me." The reporter was stunned by this honest answer but again attempted to smear what he was trying to stand for with a derisive comment. He then made a speech reassuring his acts as a hero.
Oliver decided to continue supporting the Isis Project: A Tale of Eternal Love, a project at the Metropolis Museum that he began funding while he was in a relationship with Chloe. Oliver was taking a tour of the Metropolis Museum while discussing with its curator, Adrianna, on his big entrance as Green Arrow. Tess entered, implying that he was doing that with hope that Chloe saw it and poked fun at Oliver, saying that he was nothing more than a caricature of himself and not the man Chloe fell for. Oliver responded by asking her whether or not she even knew what real love looked like anymore. Later in a conversation with Clark, Oliver said to his friend that he knew how it was living without love and living without love was just sort of existing, alluding to how much he missed Chloe. Later Clark called Tess to be the new Watchtower and Oliver was clearly against the idea, saying that no one could replace Chloe. Later Isis, possessing Lois, sensed Oliver behind her and noted that he had a brave heart but that it belonged to a lonely soul trying to fill the emptiness inside but nothing that he does works.
The next day, Tess and Oliver talked at Watchtower where Oliver admitted that Tess was one of the only people who could see right through him. Tess pointed out that Chloe was the one who saw him, too. In that moment, Oliver opened up about his ongoing heartache. "God, I miss her... I miss her laugh and... her strength...the way her eyes lit up when I entered on the room...She really loved me". He felt guilty thinking that Chloe did what she did because of his secret and Tess said that, when it came to him, no price was too high for Chloe. Oliver responded, "I guess you can still see real love," pointing out that Chloe was his true love.
After being attacked while patrolling one night, Oliver ran to Watchtower for first aid. He found Tess exercising her new role at the Watchtower and that she made some modifications on Watchtower's decor, much to Oliver's dismay, who wanted to keep Chloe's memory in it. Oliver continued to remain cold and distrustful of her, no matter how much she tried to help, implying that Chloe was better than her at the role of Watchtower. After a few tense words, he confessed to Tess that everything in Watchtower reminded him of Chloe: all the moments they shared there together, their love, so it was hard for him to be there with somewhere else.
During Clark and Lois' engagement party in Watchtower, Carter spoke to Oliver, saying that even though he had married Shayera a hundred times, he'd had to lose her that many times as well, comparing Shayera to Chloe. Carter apologized about the loss of Chloe and said that he understood losing her was difficult. Oliver clearly didn't feel like talking about it, since the pain of not having Chloe there was visible and commented that he hoped that Clark and Lois never felt that kind of loss. With that, Carter said that all relationships involve that risk, but if he learned one thing in all these thousands of years, it was that "Fear never should decide love". Oliver appreciated the comment and proposed a toast to the future husband and wife.Oliver began having flashbacks of Chloe experimenting on him after being captured by the VRA and committed himself to the mental ward at the hospital. Clark came to visit Oliver who was now in a straight-jacket at the hospital and asked him about the visions. Ollie found out Clark had been having the same visions about Chloe, but didn't believe Chloe would do that. Clark left and Ollie demanded he come back. When he didn't, Oliver saw the lights go out and the walls shape grew unusual. The shape of the wall formed into a human and Chloe emerged from the wall. He believed he was hallucinating from the drugs they injected him with, but she told him he isn't insane. She revealed that she was there to save him, but he didn't believe it due to the visions he had. Chloe asked him if he truly believed she could ever do that. His brief pause indicated that he still believed in her, but he soon after demanded an explanation for his and Clark's visions of her. Chloe explained to him that the government trapped everyone's minds in a virtual reality to find out how to control their powers. She also explained that she was trying to pull them out when she found them, but when she did their bodies shut down, forcing her to plug them back in. So instead, she hacked into the computer and created an Avatar of herself to enter the virtual reality and rescue them from the inside out. Chloe told him that believing everything in the virtual reality was fake gave her power. She demonstrated her power by opening the locked door. Oliver began to see the reality as Chloe did and made the straight jacket disappear to his surprise. Chloe explained that he was the one that did it. Chloe proceeded to lead Oliver out of the building and explained that there were virtual avatars that would kill them if they find them. Two cops saw them and Chloe asked Oliver if he trusted her and when he answered "With my life", she pulled out two unknown guns and shot the cops. Oliver and Chloe headed out afterwards. Chloe texted Clark to met her and Ollie at the top of the Daily Planet. There she explained to him what was going on and to escape this virtual reality they had to jump off the roof. Clark didn't believe them. Oliver tried to convince him to come with them but Chloe warned Oliver that if Clark didn't believe he was in a virtual reality, the jump would kill him. So Chloe and Oliver made the leap back into the real world without Clark. Oliver woke up in the VRA facility and found Chloe waiting for him. Shocked to see her, Ollie asked if they were dead. To prove they were very much alive, Chloe pulled him close and they shared a passionate kiss. Two men arrived: Rick Flag and Deadshot with guns pointing at Ollie, but Chloe told them to stand down—and they did. Oliver realized that Chloe was working with them and she said that she did what she had to do. Flag had Green Arrow and Deadshot cover the facility perimeters against the VRA troopers coming in while Chloe reentered the virtual reality to rescue the others. Later Oliver, Flag, Deadshot, as well as Dinah rescued Chloe from the VRA troopers. Afterwards Chloe met Oliver at Watchtower. Oliver gave her flowers and admitted that he stopped looking for her because he thought that's what she wanted. Oliver noted that she could have called him, but Chloe explained that the Fate helmet warned her to stay away. If she had reached out to him, she would have given in and stayed: but that she'd dreamed everyday of returning to him. She then assured Oliver that she'd be staying for a while and they passionately kissed.
Chloe and Oliver made love in Watchtower and awoke to see a Pro-Hero Rally in Metropolis online. Both Chloe and Oliver went to the Kent Farm and along with Martha Kent, Lois and Clark watched the VRA announcement and were all very happy to hear that it was repealed in a nationwide vote.
Chloe met with an in-disguise Oliver at the Ace of Clubs for a date. They lied about their identity to get a table, unaware that the names they took were actually a couple of undercover FBI agents. The two were ambushed while getting into a limo and were locked in the trunk. They were taken to an apartment where they were questioned about the disappearance of the real agents and the recent string of murders. They managed to render the agents unconscious and discover that the darkness was behind the murders. They went to investigate Desaad, where Chloe was abducted by him. After Chloe was rescued and Desaad put away by the combined efforts of Clark and Oliver, Chloe and Oliver reunited at Watchtower. They talked about their relationship and Chloe made the step Oliver was hoping for and said she can be referred to as his girlfriend and that they would go from there. On their way out, Oliver stayed back to shut down Watchtower for the night, where it was revealed that he had been marked with an Omega symbol.
After drinking some charmed champagne from Zatanna at Lois and Clark's pre-wedding party, Chloe, Oliver and the rest of the group got magically drunk. Chloe woke up in Clark's room the day after, dressed in a wedding dress with a ring on her finger and no memories from the preceding night. Discovering half of a marriage certificate with her name written on it, she concluded that she married Clark, since the latter was also wearing a ring. In the mean time, Oliver, who woke up on train tracks with Lois, agreed to help her find her lost engagement ring. That brought them to the Fortune Casino and they were later rejoined by Clark and Chloe who had been investigating the happenings from the night before.
After recovering Lois's ring and saving Emil, they all got back to the Watchtower to watch the recorded video from their wild night out. While the others were all focused on the video, Chloe and Oliver exchanged glances. Chloe eventually snuck out, but she was soon followed by Oliver who told her that he knew she was considering leaving again. He told Chloe that he understood she could not spend her life as Watchtower. He then gave her the other half of the marriage certificate, revealing that they were the ones who had gotten married the night before. Oliver then stated, "I don't know what you're thinking, but I hope it's not that you're gonna run off without your husband. You didn't take that job in my hometown for nothing." Chloe smiled and they shared a kiss before walking off to leave town as husband and wife.
In Star City, Chloe moved in with Oliver and the two began living together, mixing in their apartment her geek chic and Oliver's hero green predilection.
Oliver and Chloe were decorating the aisle at the wedding chapel for Clark and Lois's wedding while reminiscing about the missing memories that was their wedding night. They told each other that they would have gone through with it even if they hadn’t been under Zatanna’s spell. Oliver told Chloe that she needed to make sure Lois was on time, as she had apparently gone missing for her wedding. Oliver and Chloe later took their positions as best man and maid of honor at the wedding.
Near the final moments of the wedding, Oliver handed Lois the ring for Clark, and Chloe, mere seconds before it is placed on Clark’s hand, realized that it was made of gold kryptonite and knocked it away before it could be put on Clark's finger. Chloe then tried to speak to Oliver and Clark realized that he had become completely corrupted by Darkseid and told Chloe to get everyone out of there. Clark managed to free Oliver from Darkseid's control and Chloe decided to leave for Star City to get to her database. Before leaving, she and Oliver kissed under Darkseid's Apokolips as it descended upon the Earth.
Six months later,The now married couple of Oliver and Chloe Sullivan-Queen currently resides within the walls of Watchtower, back in Metropolis. Oliver, in his Green Arrow getup, finds himself without work in Metropolis, as Superman has kept the streets clean for months. When Chloe asks if his night was long, Oliver admits it was "quiet, as always." The two share a coffee together as they wait for any signs of Superman before resuming their previous plans.
At Watchtower, when Lois refers to her "forever-fiancé", Chloe apologizes for her and Oliver being married while Clark and Lois have yet to be. Chloe commiserates, acknowledging how tough it is when Oliver is currently rebuilding Queen Industries while going out and being a hero, as she's busy taking care of Watchtower and setting up a similar hub in Star City while working her day job as a reporter for the Star City Gazette.In Smallville, Chloe and Oliver are searching through the crashsite for the missing ship, where Oliver lights a flare arrow to help them see. Oliver admits he wished they had brought back-up, considering their past experiences with aliens, specifically Kryptonian survivors but Chloe dismisses his concerns. They then stumble upon the ship, which has a Queen Industries logo branded on the side,and then a trail of footprints.
In Smallville, Chloe and Oliver follow the trail of footprints which also have burn marks surrounding them. As they search, Oliver questions Chloe whether or not she wants to leave Metropolis for Star City, as she seems reluctant. She admits she doesn't wish to, but knows that they need to in order to officially begin their adult life, saying it is different from the awe of Metropolis. Oliver disagrees, stating it has the second highest crime rate in the country behind Gotham City, but Chloe admits she is fine with that. They find a second trail of prints as well as small drops of blood. The two ready their weapons, as someone watches them from behind.
Meanwhile, Oliver and Chloe meet the survivor of the ship crash. It is Chloe's counterpart from Earth-2. Earth-2 Chloe explains what has happened in her reality before she is killed by an unknown figure. Her last words reveal that Earth-2 has been destroyed.
Meanwhile, at Metropolis General Hospital, Oliver and Chloe look at Earth-2 Chloe's corpse. While she is shaken up by the sight of an alternate version of herself, Oliver tries to comfort her, telling her to contact Clark in order to tell her a crisis is coming.
At Watchtower, where Chloe gets a disturbing phone call from Emil at S.T.A.R. Labs. Oliver arrives with coffee for Chloe. Chloe tells Oliver that Emil is close to accessing the black box from the late Earth-2 Chloe's space ship. Meanwhile, Oliver has no lead on whoever it was in the cornfields that killed Chloe-2. Plus Oliver's been getting gibberish emails that he'd like Chloe to get to the bottom of, if she's not too distracted by this "Crisis". Next thing you know, Watchtower's Trouble Alert which alerts them to a prison breakout at Stryker's Island. Oliver gets his Green Arrow suit and bow and arrow and immediately heads to Stykers. After a fight between Ollie and Nightwing, Green Arrow races out of Stryker's, confirming Chloe's report that not only did Superman and Batman break Mannheim out of prison, but that Batman has a hovercraft that's invisible to radar. Ollie suggests to himself to make further investments.At Watchtower, Chloe jokes with Ollie over getting beat up by a 19-20 year old girl, mentioning that the Wonder Twins are a call away. The talk leads to encrypted e-mails Ollie's been getting and while there is a pattern, Chloe says he won't like where it leads. News stations cover the pursuit of the "murderer Batman kidnapping a wounded Superman" just as Lois and Ollie meet up (wondering where Batman is taking Superman) and Chloe is hacking into the traffic system so no one is hurt during the chase.
Nightwing takes control of the Batmobile, leading it outside the Leviathan ship. Batman performs the surgery inside the car, just as Lois arrives and she sees it happening. After getting the bullets out, Batman reprograms his vest and splash Clark with yellow sunlight, just as the police report that they lost the Batman. Chloe is relieved that it's over, but Batman and Nightwing respond that it isn't: they need to make sure that the authorities know it was Mr.Freeze and The Prankster who killed Intergang contact and weapons dealer Joe Chill. Ollie agrees, but also asks for his lawyer to be called too (he's been arrested).
In interrogation: Ollie tells the interrogator, yet again, that he was not helping a criminal escape but helping another hero who needed medical attention after being hurt by two other villains. The interrogator doesn't believe it, but then two agents enter and inform the interrogator that Ollie's representative has arrive with proof that Batman is not a murderer, Green Arrow is innocent, as well as the two men responsible are Prankster and Freeze. And who is Ollie's representative? His wife, Chloe.
Later, Oliver and Chloe talk about the possibility of Mia Dearden become his (Oliver's) sidekick after seeing Nightwing and Batman in action. Just then, it starts to snow. The reason is Superman used Mr. Freeze's freeze gun to create snow. At last, Chloe reveals that she is pregnant.
At Watchtower, Oliver sits at the desk, drawing plans for a jetcraft amidst a number of parenting books. Chloe practices shooting his bow and arrows and Oliver notes that she seems to be getting better. Chloe attributes it to their child growing within her. When Ollie notes that he's the only one of the two who has spent any time with the books, Chloe teases him that he's only been doodling images of the Batwing. He shows her his plans and proudly proclaims it is the Arrowjet.
Ollie then asks why she hasn't told her best friend or her cousin about the pregnancy and admits to being anxious to let everyone know. Chloe reminds him that as long as Clark is irradiated and being tracked by Lex, she doesn't want to risk Watchtower's location being discovered. Besides, she is more concerned, at the moment, with decrypting the warning her doppelgänger gave regarding "the Crisis" that is coming. Ollie laments that they can't just ask her as she is dead. Chloe makes a suggestion that there might be a way that they could.
At S.T.A.R. Labs, Oliver and Emil reveal that they were able to place Chloe's dead doppelganger in cryogenic freeze. Naturally worried, Oliver asks if the plan will work and if they'll even be able to access her memories. Emil posits that Chloe might only be able to access the other's most recent accessed memories given how long she's been dead. Oliver guesses this to mean the flashes of her life before her eyes just prior to dying. Looking for assurance, Emil is only able to admit that with the technology and the similar biochemistries of the two Chloes, he's making educated guesses as they're going along. Oliver asks if the baby will be affected by the procedure and Emil says that unless there are psychosomatic effects caused by the mental link, the baby should be fine.
Meanwhile, Emil places Chloe inside the Project Intercept apparatus to begin the "mind dive" procedure. Oliver asks one more time if she's sure about doing this. Mentioning that she's "been possessed by a witch, rewired by a Kryptonian computer, as well as mind controlled more times" than she can count, Chloe assures him that she's prepared for what she is about to do.
In Metropolis, Chloe gets frustrated that she can't do help more and can't sort out her counterpart's memories. Suddenly, she's stricken by a memory and falls into Oliver's arms. Back in the present on Earth-1, Chloe mutters dismayed words from the memory.
Chloe 1 finishes explaining the memory to Ollie while in the tub. They're both baffled by the supposed romantic encounter between their doppelgangers. Chloe asks if Clark and Bart had any luck in Utah. A speed storm alert on Ollie's phone tells them no.
Chloe wakes up again in Oliver arms with her wondering with what happened with Bart, the lives the other Oliver and Chloe lead, the lives Green Arrow and Watchtower lead, the destruction of Earth 2, how can they bring a baby into the universe with a crisis on the way.
Later, Oliver and Chloe decide to leave away from any action so the baby can come safely to term.
Months later, when Chloe accompanies Lois at the Daily Planet, Lois asks about Oliver and Chloe says he is in San Francisco, where he just closed a deal for Queen Industries to provide financial assistance in rebuilding Pier 39. Chloe says the more they help cities get back on their feet after super-related disasters, like they did with Washington and San Francisco, the less crime will have the chance to take advantage of the situation.
In Metropolis, Oliver and Chloe talk about their upcoming child. Oliver, seeing his equipment says that he misses the action. Chloe responds by saying that even though they don't like the fact that they are away from any action and danger, as they decided to do, they have to stay that way so their son would have an intact set of parents when he is born. Chloe also reminds to Oliver that they both lost their parents, who weren't even directly in the line of daily fire. Oliver agrees but says that at least Chloe had the opportunity to go to Gotham City.
Chloe read a Smallville comic book to her son before he went to bed. After reading the book, Chloe kisses his forehead, showing her left hand with a wedding ring on it and said goodnight to him even though he wanted her to read the story again.
Chloe headed for the door, but before she closed it, she smiled as she glanced at her son as he was asleep, then her eyes turned to the red-and-yellow arrow set in the son's bedroom. The boy opened his eyes and looked straight at the arrows.
In the alternate future where the Kandorians were in control, Chloe and Oliver were the leaders to the Resistance against Zod and his men. They were united in their distrust of Clark, since he left. Chloe shot Oliver's former lover, Tess, with an arrow which killed her and Chloe justified her actions, saying that she had the shot and she took it. Chloe was not much later stabbed and murdered herself. Oliver did not display much emotion to her death, continuing with the critical mission that her team was determined to complete, but he remained by her side to fight off oncoming Kandorians and face certain death.
Oliver and Chloe were involved in an alliance with romantic undertones in a possible future from there.
Season Eleven (Earth-2)
At Chloe's apartment, the Earth-2 Oliver practices shots with a bow and arrow: his skill is far off from his Earth-1 counterpart. Chloe drinks whiskey and they talk about their plan to take down Clark Luthor. Oliver worries he'll irk people by trying to dig up the town of Smallville in search of the meteor rock they'll need. Chloe dismisses his concern and tells him it's the only thing that will work for their cause. She then asks why he's there with her instead of with her cousin, his girlfriend. Oliver announces his going to ask Lois to marry him, to which Chloe laughs and snidely rejects the notion.
Chloe corrects his shooting posture and he nails the bullseye. They both acknowledge that they've got but one shot against Luthor and it must count. They embrace and kiss.
Later, Oliver has called a press conference to reveal that Ultraman is really Clark Luthor and to announce that Queen Industries is going to provide every citizen of Metropolis with a personal amount of "meteor rock" with which to defend themselves from the villain. Meanwhile, Chloe is waiting with a sniper rifle and a Kryptonite bullet with which to shoot Ultraman, whose appearance on the scene is fully expected. And appear he does, fully aware that it's a trap, as well as snapping Oliver's neck when Chloe fails to shoot for apparent fear of hitting Oliver.
Chloe's letter to Oliver
"Oliver... I never thought I'd have to tell you how I feel about us, because the smile on my lips when I looked at you... pretty much said it all. But now that you won't be seeing it anymore, I'll have to use words to tell you. I've never loved anyone the way I've loved you. And I never will again. You will always be my brightest star, my knight in shining leather, my hero."
- Chloe: Clark! Oh I'm sorry I did't realize you have company
- Clark: Chloe...Oliver Queen
- Chloe: Oh Hi! I feel like I know you already Lois talks about you all the time
- Oliver: I was actually just gonna go see Lois right now. Maybe it's time we make some talking...Well look I'm looking foward your article on Dark Thursday, I hope my satellite images help
- Chloe: Yeah
- Oliver: Good...It's good to meet you
- Chloe: (To Clark ) Wow! In person he is really... WOW!
- Season Six, Reunion
- Chloe: Someone ask me when the last time I had a good time was and I didn't had an answer
- Oliver: I don't think anyone could fault you for being on edge Chloe. Now if anyone could related to me I get it
- Chloe: Yeah you can
- Oliver: You know sometimes, you've gotta take your fun where you can get it. And sometimes, it's right in front of your face. You just have to want to see it. Come on
- Chloe: How do I know when to let go?
- Oliver: It's all about your heart. Just listen. Right there, in between the beats. That's when you let go.
- Season Nine, Warrior
- Chloe: Maybe we just should said next time you won't take advices about relationships from Clark Kent
- Oliver: You know, speaking of Clark...for future references and you know strictly for environmental purposes; next time you wanna take a shower with someone, Chloe you can just ask me.
- Season Nine, Escape
- Chloe: You know, Oliver, now that Green Arrow is officially on Checkmate's radar, I think it might be a good idea for you to just hang your tights for one night. Go civilian.
- Oliver: Well, th-they're not tights. They're not tights! But I see your point. Yeah, hmmm, unfortunately for me, uh, that means attending a LuthorCorp shareholder dinner which -- yeah, I'd rather be shot at.
- Season Nine, Checkmate
- Chloe: Hi.
- Oliver: Hey.
- Chloe: Thanks for keeping my seat warm, at Watchtower.
- Oliver: Well, you're welcome. Don't get used to it.
- Chloe: Aww, but your timing is so good. I mean if you hadn't flipped that castle's electric switch when you did, I would--
- Oliver: Chloe.
- Chloe: But I, y'know, I kinda liked being out in the field, knowing I had a warm bed to come home to.
- Oliver: That's very, very funny. You scared the life outta me.
- Chloe: You better be careful, Ollie; I'm gonna start to think you're falling for me.
- Season Nine, Checkmate
- Oliver: (To Tess about Chloe ) God, I miss her... I miss her laugh and... her strength...the way her eyes lit up when I entered on the room...She really loved me
- Season Ten, Isis
- Oliver: I'll rush this guy, you make run for it
- Chloe: No no, I can handle it. I just need to know one thing...Do you trust me?
- Oliver: With my life
- Season Ten, Collateral
- Oliver: I just stop looking for you...Figure it that's what you want. Right?
- Chloe: You have no idea how much it means that you trust in me.
- Oliver: You could have call me. You could have call me and said uh...
- Chloe: Yeah I wanted to but the fate helmet warn me to stay away.
- Oliver: Did the helmet said anything about how I be sitting alone listening old voice mails just to hear your voice? Anything like that or that I be scaning every single strangers face on the subway just in hopes that I came across your smile? Never to find it.
- Chloe: No, it didn't tell me that. I figure it out on my own. Oliver I didn't reach out you because I didn't trust myself, I knew that if I looked into your eyes or felt your breath on my cheek there is no way I would walk out that front door. And there's hasn't been a day that's gone by that I haven't dreamed about the time when I walk through you again.
- Oliver: Are you sticking around for a while?
- Chloe: Yeah
- Oliver: Good
- Season Ten, Collateral
- Oliver: You know when I said I wanted to spoon earlier this isn't really what I had in mind
- Chloe: We're lying alone together in the dark ok?, I think that counts for something
- Oliver: Yeah you're probably right this is definitely the most romantic of my recient kidnapings. Hell boy to spend an aniversary right?
- Chloe: ...
- Oliver: Oh you forgot
- Chloe: No no no I did not forget that it's been a year since we start doing...whatever it is that we're doing
- Oliver: Whatever it is? Wow. You weren't jocking around in the restaurant were you? you don't know how to call me
- Chloe: Not in so many words
- Oliver: Ok
- Chloe: Oliver come on
- Oliver: We spent every waking moment together, right? we said "i love yous" how many times? several! what do you call that?
- Chloe: Can we talk about this later?
- Oliver: Yeah no I would love to do that, if there is a later
- Chloe: You are so dramatic
- Season Ten, Masquerade
- Oliver: You're leaving again, right?
- Chloe: Oliver, I -
- Oliver: It's okay, I can - I can read between the lines... Chloe, I never expected you to sit up in that ivory Watchtower for the rest of your life. I know better than that. I have something, uh... (gives her half of the certificate) Now, I don't know what you're thinking, but I hope it's not that you're gonna run off without your husband. You didn't take a job in my hometown for nothing.
- Season Ten, Fortune
- Chloe and Oliver dated for five months before her disappearance.
- Chloe Sullivan is the only woman Oliver ever said "I love you" to, on the show.
- As of Masquerade, Chloe and Oliver have been together for one year.
- Oliver is Chloe's second husband after Henry James Olsen.
- Chloe's child in Finale has not his name officially given by the series. Al Septien and Justin Hartley implied on Twitter the fact the boy is actually the son of Chloe and Oliver. 
- In comics and also spotted on Oliver Queen Chronicles, Oliver's mother's name is Moira Queen, which means both Chloe and Oliver have mothers named Moira.
|Chloe Sullivan in Smallville|
|Oliver Queen in Smallville|
- ↑ In Reunion, she acts flustered when they first meet and says, "He is really... Wow!" and staring at him as he leaves.
- ↑ Tess stated this in Shield.
Still with that, in SV chronology, their relationship started before Valentine's Days till September (Salvation/Lazarus timeline), which would made them have six or seven months together, not five.
3. ↑ This convo sort of parallel Isis/Osiris story with Chloe/Oliver.