- "A girl like that? Worth spending the rest of my life in a body cast." - Jimmy Olsen, about Chloe Sullivan, Trespass.
- "Actually, you know what? There aren't any stories... Oh, except I did meet this really hot young intern from Metropolis High. It was great. Made me forget all about Smallville for three whole months."
- — Chloe Sullivan to Clark Kent, Heat
- "His name is Jimmy. He was very cute, in a bowtie kind of way. You know, it was a summer infatuation that I thought was the real thing."
"Do you wish you hadn't done it?"
"Sometimes. I mean it wasn't awful by any means, but it just wasn't special."
- — Chloe Sullivan to Lana Lang, Unsafe
Jimmy met Chloe when they were high school interns at the Daily Planet during the summer of 2002, and began a whirlwind romance. Chloe lost her virginity to him that summer. However, later Chloe confessed to her friend Lana Lang that she had kept it a secret because she regretted the sex, not because it was bad but because she felt it hadn't been special.
- "Okay look, I know we planted our flag on the summit of intimate territory back when we were interns, but... and it's not like I woundn't mind exploring that territory again one day."
- — Chloe Sullivan to Jimmy Olsen, Wither
- "I had a feeling this was coming. Look, Clark, despite our differences, I think you're a decent guy. Chloe obviously thinks you can walk on air, so... who am I to stand in the way?"
- — Jimmy Olsen to Clark Kent, Trespass
Four years later, Jimmy got a photography job at the Daily Planet during Dark Thursday and reunited with Chloe there. After they survived Dark Thursday, Jimmy wanted to reconnect with Chloe, but she was initially reluctant. However, when they are staking out a "good story" at the local make-out point, she agreed to rekindle their relationship, but wanted to take it a little slower this time.
Jimmy went to Chloe´s apartment to take Chloe on a romantic dinner, but his plans are scuppered as Chloe had to look after Javier Ramirez. Jimmy wanted Chloe to move to Metropolis, as he felt Smallville was strange and dangerous, but Chloe told him that she liked living there.
When Jimmy tried to set up Lois with Clark in a Valentine's Day party, Lois infected Clark with red kryptonite. Then Jimmy brought up Clark's irrational behavior and was upset when Chloe defended Clark. He argued that Chloe would probably rather be with Clark if she had the chance and suggested they take a break. Eventually, Jimmy decided to believe Chloe when she told him that she would rather be with him and they made up.
They continued dating, and one night Chloe disappeared after she was identified as being meteor infected. She kept this fact secret from Jimmy, with made him believe the kidnapping was because she witnessed a crime. This incident made Jimmy realize how much Chloe meant to him. Aiming to rekindle the romance between them, Jimmy invited Chloe to a private screening that he set up in the empty basement of the Daily Planet, but their romantic moment ended abruptly when they heard a gunshot. Chloe helped Jimmy investigate who shot Lana Luthor at the Daily Planet office. At the end of all this, Jimmy confessed to Chloe that he he accepted an out-of-town assignment, and she was excited for him. Then, Jimmy and Chloe parted on optimistic terms.
- "Wait a sec... is this because of Kara? Because, after all the times that you left me on hold to go run off and help Clark, I hate to think that you're gonna' give me a hard time for helping Kara once!" - Jimmy Olsen, Cure.
When Jimmy returned to Smallville, Chloe chose not to tell him about her meteor rock infection because she was worried what Jimmy would think about her new "meteor freak" powers and started to become less open with him. After nearly being frozen to death by a meteor freak, Jimmy declared that he would help Chloe get rid of the meteor freaks but did not notice Chloe's unease at the subject.
After Chloe abruptly canceled an elaborate evening Jimmy had planned in order to secretly undergo a radical treatment, Jimmy was upset and annoyed. Fearing the treatment would cause memory loss, she wrote Jimmy a note asking him to "remind her why they should be together." After she saw Kara and Jimmy spending time together, she threw the note away instead of giving it to him. Jimmy read it anyway and was unsure of its meaning. When Chloe returned without having had the treatment and with her memory intact, Jimmy expressed optimism that from now on, their relationship would only be "normal." Chloe was unable to promise him this and refused to tell him what was bothering her. Frustrated at her persistent lack of explanations, Jimmy admitted that he couldn't be the patient boyfriend anymore and they broke up.
Chloe was still keen to remain friends, but Jimmy was more interested in pursuing his relationship with Kara. Their subsequent relationship remained awkward and at Christmas they bumped into each other at the elevator. Jimmy was keen to avoid any awkwardness and went to take the stairs but Chloe encouraged him to get in. However, they then became stuck in the elevator with a bomb.
Thinking they were about to die, Chloe confessed that she pulled away from him because of her meteor infection. Relieved that she had finally shared her secret, Jimmy kissed her. After they were rescued, Chloe displayed her power and Jimmy hugged her and said it didn't change how he felt about her. They were then slowly able to build bridges in their relationship, starting with a close friendship. But when Jimmy realized that his relationship with Kara was fizzling out, he asked Chloe if she wanted to go get a cup of coffee, to which she agreed.
Jimmy continued to put a lot of effort into their relationship weeks later, but Jimmy continued to display the same insecurities and was upset that Chloe seemingly blew him off. An agent of the Department of Domestic Security convinced Jimmy that Chloe was part of a terrorist sleeper cell and forced him to spy on Chloe. The two attended to the Ace of Clubs opening and ended up fighting Department of Domestic Security personal with Chloe being tortured by Special Agent Vanessa Webber. He rescued Chloe and took her home and demanded the truth. Thinking they are about to get arrested anyway, Chloe challenged him to ask her whatever he wanted. He asked her if she wants him more than she wants Clark. Chloe didn't answer, but kissed him back. Jimmy was pleased and admitted that the government wouldn't be coming after either of them. Unbeknownst to Chloe, it was actually Lex that prevented her from being arrested and continued to blackmail Jimmy with Chloe's freedom.
After recovering from a Brainiac-induced coma, Jimmy realized how much Chloe meant to him and decided to propose in the Talon with a plastic wedding ring. Before Chloe could answer, she was suddenly arrested for terrorism by the DDS.
- "And what I've lost... I've lost so much, the only thing I really miss is you." Chloe Sullivan to Jimmy Olsen, Doomsday.
A month later, Chloe returned to Smallville and Jimmy found her at the Talon. He tried to retract his proposal saying it might risk what they have between them, but she accepted his proposal after all. Jimmy moved into Chloe's apartment and found Chloe's letter to Clark that she wrote when he was sick and became angry about it and wondered why she had never said those things to him. A furious Jimmy tried to see another woman to make Chloe jealous, and collapsed from an endorphin overload. At the hospital, Chloe convinced Jimmy that he was the one she loved.
Chloe and Jimmy had a party to celebrate their engagement and after they leave, were abducted by a psychotic jeweler that subjected them to a lie detector. He began asking questions about Jimmy's infidelity and finally asked if Chloe was in love with anyone else. When Jimmy told her not to answer, the abductor shocked him and repeated the question, to which she replied "no." The lie detector proved she was telling the truth, so they were released. When they woke up in their bed, Chloe told Jimmy she couldn't have survived with anyone else across from her. This made him realize that they couldn't have secrets between them, so he revealed a secret about his family and Chloe embraced him.
Brainiac began removing Chloe's memories, and she forgot her fiancé. Jimmy showed her photographs of them as a couple to try to help her recognize him. Jimmy found this very traumatic, but with the help of Clark, Chloe recovered and excitedly continued to plan her upcoming wedding.
In late 2008, Chloe and Jimmy were married, but the reception was interrupted by Davis, who had transformed into Doomsday, who was clearly influenced by Davis' growing feelings for Chloe. Doomsday killed numerous people and seriously injured Jimmy, who was later sent to a hospital in Star City. Chloe traveled back and forth between Smallville and Star City to care for Jimmy. He recovered five weeks later and was transferred to Metropolis.
He and Chloe reunited and seemed happy and attempted to begin their new lives together as husband and wife, but one night Jimmy awoke to find Davis killing a man in the hospital elevator. He tried to expose Davis, but Chloe didn't believe him as she thought it was a drug-induced hallucination. This angered Jimmy and despite Chloe later trying to express that she loved Jimmy with all her heart, he had an angry outburst and admitted that he felt that marrying her was a terrible mistake on his part due to the lack of trust she had in him. He left Chloe heartbroken and alone.
They finally reconciled after Jimmy discovered Clark's secret and understood why Chloe had been with Davis. However, as Davis overheard this discussion he went into a murderous rage and killed Jimmy. Before he died, Jimmy saved Chloe from being killed by Davis and then passed away in Chloe's arms after professing his love to her.
- Like Clark and Lana, Chloe and Jimmy lost their virginity to each other, but it happened before her sophomore year started, which makes Jimmy guilty of statutory rape as she had not reached the legal age of consent (16 years old) in Kansas. She would also be guilty if he had also not reached the age, although the penalty would be limited due to Romeo and Juliet laws if their age difference is less than 4.
- Despite being quite supportive of her cousin and on good term with Jimmy, Lois Lane was very sceptical of Chloe's relationship with Jimmy, and drunkenly complained to Clark on Chloe's engagement party (she being the maid-of-honor) that Chloe was "barely legal" and "getting herself hitched to the first guy who's shown her any attention". She later almost ruined the party with outspokenness.
- Their relationship was fairly rocky throughout, as Chloe never quite loved Jimmy as much as she loved Clark, or later on, Oliver. Chloe rarely trusted Jimmy with deep secrets, and Jimmy was horribly insecure about their relationship despite all of her reassurances. Over the course of the series:
- Chloe regretted having lost her virginity to Jimmy, holding that it was not as special because it was during a whirlwind romance (Unsafe), and she realized she still had feelings for Clark (Heat).
- Chloe never revealed her true feelings about Clark until Jimmy accidentally found her letter to Clark, which triggered an emotional fallout (Instinct)
- Jimmy dumped Chloe many times (Crimson, Cure), flirted with and briefly dated Kara (Lara), and publicly humiliated and divorced Chloe. (Turbulence)
- Chloe never told Jimmy about her Brainiac infection, although he also didn't open up to her about his background until after their abduction and interrogation by a psychotic jeweller. (Committed)
- Jimmy tried to back out of their engagement twice (Odyssey, Instinct), and even suggested Chloe to back out of the engagement after their engagement party. (Committed)
- Chloe never hesitated to lie to Jimmy to protect Clark. (Identity)
- After divorcing Chloe, Jimmy sent her cruel emails that "included every single unflattering word in the dictionary, including some that didn't get past the censors". (Eternal)
- Addicted to painkillers, Jimmy tried to steal money from Chloe after their divorce, and was caught fumbling through her apartment by Oliver Queen. (Beast)
- Chloe did not wait long after their divorce to try to start a new relationship with Davis Bloome (Eternal), though she claimed it was done mostly to protect Clark; or to date Oliver Queen less than a year after Jimmy was killed. (Warrior).
- Ironically, in the last days of his life, Jimmy worked for the very person who would soon replace him in Chloe's heart: Oliver Queen.
- Chloe: Thanks, Jimmy but I can't exactly run out to Smallville for frozen sweet corn. I've got stories I've got to file.
- Jimmy: What's gotten into you? Chloe, someone set this girl's dial to deep-freeze. This has "meteor freak" written all over it. It's exactly the kind of story that your new editor ordered.
- Season Seven, Fierce
- Jimmy: You know, when we first got together I thought that you were pretty prejudiced... Quick to jump to the conclusion that some meteor-infected murder was behind every bad thing that happened in Smallville.
- Chloe: Jimmy...
- Jimmy: But you were right. I've seen enough now to know that sooner or later they all... snap. So, from now on, it's open season on the infected. What do you say we clean up this town, partner?
- Season Seven, Fierce
- Chloe: What is this place?
- Jimmy: It's your wedding present. Well, it was. I was gonna give it to you after the reception, but...
- Chloe: My wedding present?
- Jimmy: It needs some work. I know. But... So did we. I just... I saw us here, you know? Starting our life together, taking something that the rest of the world had forgotten about and... making it ours.
- Chloe: You can see all of Metropolis from here.
- Jimmy: From anywhere in the city, you can spot this place. I thought that no matter where you were, you could look up, and.. You could see our home You could see me watching over you.
- Chloe: I don't know how you do it. You always seem to come through. You're always there doing the right thing, saying the right words. Jimmy, there's so much that I want to tell you.
- Jimmy: I know about Clark.
- Chloe: What? What exactly do you know?
- Jimmy: The "what". I saw him. And I saw what he can do, who he is. And now I see all kinds of things. I see what you have sacrificed for him. For everyone, really.
- Chloe: That's the reason I went with Davis.. To protect Clark. That's the only reason.
- Jimmy: It all makes sense now. You are as much of a hero as he's ever been. What you have gone through, what you've risked...
- Chloe: And what I've lost. I've lost so much... The only thing I really miss is you.
- Jimmy: Well, now you found me again.
- Chloe: I'm so sorry I left, Jimmy, but I promise, I never left you.
- Season Eight, Doomsday.
|Chloe Sullivan in Smallville|
- Chloe states their relationship moved fast in Wither.
- Chloe admits this in Unsafe
- A whole entire episode Abyss pointed this out and in Beast, Chloe herself told Clark, "Everything I've ever done, right or wrong, I did it for you."
- In the season 10 episode Shield, she wrote Oliver a letter saying "I've never loved anyone the way I've loved you."