- " You know it's true love when you fight off caffeine-pumped preppies to get a girl her favorite treat." - Jimmy, Cure
After some weeks, Jimmy returned to town and was glad to be with Chloe again.
When Jimmy was photographing the Miss Corn Pageant in Smallville, he and Kara Kent exchanged several long looks, clearly drawn towards each other. However, three of the competitors noticed him taking pictures and attempted to kill him by freezing him into his car. Kara saved him and he recovered in the hospital. Later, Jimmy declared that he wanted to help his girlfriend Chloe "clean up" the city and rid it of meteor freaks.
After Chloe abruptly canceled an elaborate evening Jimmy had planned in order to secretly undergo a radical treatment, Jimmy was upset and annoyed. At the same time, he helped Kara to restore images of her missing ship and the two seemed to connect. However after Chloe saw Kara and Jimmy spending time together, Jimmy took her reaction as an abuse of jealousy bringing out the rudeness that he had to endure due to Clark and admitted that he couldn't be the patient boyfriend anymore and they broke up.
Kara and Jimmy bonded over their love of extraterrestrials and the two began to feel more attracted to each other. After helping Clark and Chloe to find the whereabouts of Kara, Kara returned and thanked him for helping her. The two then began a relationship and although Chloe was still keen to remain friends with him, Jimmy was more interested in pursuing his relationship with Kara.
Jimmy and Kara start to dating and took a surfing trip together in Coast City. However, their relationship was mitigated by the mysterious disappearance of Kara.
Apparently avoiding each other for some time, Jimmy and Chloe wound up awkwardly sharing an elevator just before Christmas. However, Chloe was unknowingly targeted by Adrian Cross. He trapped them in the elevator with an explosive device, but they were saved by Bizarro, posing as Clark. Then, Chloe revealed to him her meteorfreak condition.
Trying to help Kara's memory with familiar things, Jimmy took Kara to a OneRepublic concert, where they met Pete Ross after Pete saved Kara from a falling speaker. He wanted to interview Pete about his new stretching meteor-power, thinking that Pete could prove that meteor-infected individuals did not have to live in secret or be ashamed. Chloe and Clark tried to talk him out of the article. He went with Clark to investigate Pete's power, and witnessed Lex blackmailing Pete into stealing for him, but still believed the interview would be beneficial. When Pete got in over his head, he changed his mind about the interview, and Jimmy understood. After Pete left town, Jimmy wondered if he could rekindle his relationship with Chloe.
However, he seemed annoyed that Chloe was preoccupied with helping Clark and asked Lois if she wanted to collaborate on an article, saying he was trying to avoid getting fired. They went undercover to interrogate Lionel Luthor about the death of Patricia Swann. Lionel was not intimidated by their questions and promptly threw them out. Jimmy and Lois continued to follow Lionel to the Isis Foundation and learned that Lex Luthor was the one responsible for Patricia's murder.
After the death of Lionel Luthor, Jimmy managed to get a glimpse of Lionel being pushed out the office window. When they went to go to the Isis Foundation, they were caught by Lex's assistant. Lois was shot for trying to stop her, and was placed in a freezer with Jimmy. Clark used his heat vision to keep them warm to prevent them from dying of hypothermia.
Jimmy made a strong effort to rekindle his relationship with Chloe, but felt that she wasn't working as hard as he was. After he was approached by an agent of the DDS and was told to watch over whatever Chloe Sullivan does, he went to Isis, only to discover a confidential document of United States Security. After starting to suspect his girlfriend, he was instructed to accompany Chloe to the Ace of Clubs where he disguised, sneaked up on a man and stole his briefcase after he knocked him out. After failing to get the right information, Jimmy went back to save Chloe from Vanessa. The next day, Jimmy returned to the Planet to thank Lex for helping him to help Chloe. Lex reminded him that in time Jimmy will have to pay him back.
After Lex was attacked by a cloaked stranger who carves Kryptonian symbols into his chest, Olsen followed Lex's ambulance and managed to take a picture of the symbol. He then told Chloe about Kryptonian symbols found around Smallville in the past and began to investigate the Kawatche caves. Jimmy began to compile this information to write his first article for the Daily Planet.
Finally, Lex told Jimmy to feed Lois a fake story to keep her out of his business and very reluctantly, Jimmy accepted the request of Lex. Feeling guilty for what he did, Jimmy told Lex he could not do it any longer and Lex apparently accepted the decision of Jimmy. After Chloe was attacked and recovered 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, but before Chloe can answer, Lex take his revenge on him and called the Department of Domestic Security on Chloe and they arrested her.