"A girl like that? Worth spending the rest of my life in a body cast."-- Jimmy Olsen, about Chloe Sullivan, Trespass

Chloe met Jimmy when they were high school interns at the Daily Planet the summer of 2002 and began a whirlwind summer romance. Four years later, Jimmy got a photography job at the Planet during Dark Thursday and reunited with Chloe there. Jimmy wanted to reconnect with Chloe, but she was initially reluctant. However, they later agreed to rekindle their relationship, but take it a little slower this time.


Chloe assures Jimmy that she and Clark are just friends in Subterranean.Jimmy wanted to take Chloe on a romantic date, but they wound up staying home to babysit Javier Ramirez. Jimmy told Chloe that he thinks Clark doesn't like him because Clark is madly in love with her, but Chloe assured him that that wasn't the case. However, Jimmy remained simultaneously perplexed and jealous of Chloe's devotion to Clark, even though both Clark and Chloe told him repeatedly that they were just friends. Jimmy approached Clark and attempted to resolve the awkwardness between them, but Clark just looked confused. Jimmy wanted Chloe to move to Metropolis, telling her that he thinks Smallville is strange and dangerous, but Chloe told him that she likes living there.

When Clark was infected with red K and crashed Lex and Lana's engagement dinner, Jimmy brought up his rudeness to Chloe and when she defended him again, Jimmy got upset. He argued that Chloe would probably rather be with Clark if she had the chance and suggested they take a break. But they were not estranged for long.
Jimmy and Chloe kiss goodbye in Noir.As Clark and Jimmy worked to locate Lana's stalker, Clark told Jimmy that even though they are just friends, Chloe is great and he should hold onto her if he has the chance. Jimmy decided to believe Chloe when she told him that she would rather be with him and they made up. When Chloe was abducted, she did not tell Jimmy that she was suspected of being a metahuman, confiding only in Clark that she felt like she was a "time bomb" waiting to go off.
Chloe helped Jimmy investigate who shot Lana Luthor at the Daily Planet office. When he accepted an out-of-town assignment, she was excited for him and he and Chloe parted on optimistic terms.


Jimmy ends their relationship in Cure.When Jimmy returned to Smallville, Chloe chose not to tell him about her meteor rock infection. When he was saved by Clark Kent's cousin Kara, the two shared flirty looks. Jimmy declared that he would help Chloe get rid of the meteor freaks but did not notice Chloe's unease at the subject. Later, Chloe abruptly cancelled an elaborate evening in order to secretly undergo a radical treatment, and 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." Shortly after, Kara asked him to help her restore images of her ship and they flirted again over dinner. Chloe saw them spending time together. She maintained that she wasn't jealous but 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, so Jimmy admitted that he couldn't be the patient boyfriend anymore, and they broke up for good.

The relationship between Chloe and Jimmy is known as "Chimmy" by fans.