Author's Note: Since everything else interesting in Chloe's life happens off-screen, I figured she could have a grand, tragic romance with Jimmy Olsen off-screen too. I meant it to be happier, but it went in a sort of downward spiral because there's way too many complications in Chloe's life for fluff.
He wore a bowtie. A different one every single day. Once, he spilled his coffee and she discovered that he kept a spare, also different. It was all exceedingly dorky, but dorky had proven to be Chloe's type. He answered to Jim, Jimmy, Jimbo, Olsen, Oldman, Jerod, Jake, John, George, Geoffrey, Jed, Kid, and Hey You. He preferred Jimmy. Chloe had asked. No one ever got her name wrong anymore. Being the youngest columnist in the history of the Daily Planet tended to have that effect. Chloe could not help but smile as every "Chloe" or "Ms. Sullivan" (no matter how resentfully intoned) wiped away one more lingering vestige of Miss Claire Cloris Cassie Sweetheart Sanders-Sodheim-Soulders-Honey who had interned the summer before.
Technically, she was still an intern, since she was not being paid, but she spent significantly less time making coffee, getting lunch, and carrying memos than she had. Sara Lindey, the gossip columnist, whose desk was adjacent to Chloe's, started to yell for her coffee at exactly 9:03 every morning. Jimmy always smiled at Chloe as he passed--he had a great smile--and after the first week Chloe began to suspect that he was forgetting Sara's extra sugar on purpose just so that he could come back. He never got anyone else's order wrong.
Chloe waited for him to say more than "hello" for as long as she could possibly stand. He was shy, which was cute, but Chloe had never been particularly patient. The day after she figured out the coffee conspiracy she called out to him as he headed past her desk for the fourth time, and invited him to have lunch with her. Lunch consisted of eating vending machine sandwiches over a few minutes at her desk, but it was productive all the same. Chloe learned that Jimmy was smart, sweet, and--best of all, in her humble opinion--did not seem to be freakishly obsessed with some other girl.
Their first date was when Mark Clemmens was out sick and Chloe had to cover his beat. She took Jimmy along as photographer, though she really could have taken the pictures herself. Of course, if she had, she would not have been able to feel that warmth in the pit of her stomach when she noticed the few times that a shutter clicked in her direction. Later, she worried a bit since, really, what wouldn't be more interesting to take pictures of than a dog show? And even if he was taking pictures of her, he was doing so without telling her, which really weighed towards the likelihood of him being an insane stalker.
Fortunately, the next day, he rather adorably revealed himself as he gave her a framed picture of herself on the scene as a bit of memorabilia. When she coyly asked him why he thought that day would turn out to be so memorable, he flushed in a most adorable way and asked her to dinner.
Lois let Chloe borrow a dress that her father would never approve of, and helped put Chloe's hair up. His bowtie was periwinkle blue and the restaurant was a dimly lit, trendy affair, with square plates and paper lanterns.
Counter-intuitively, he seemed to fit there, and Chloe understood why when she learned that he had grown up in Metropolis. Instantly, attraction was supplemented by kinship, and Metropolis boy and Metropolis girl found many things to discuss about the city. Especially when Chloe began to speak on Smallville. The comparisons and Jimmy's incredulity were even better.
He was not like anything from her life in Smallville. Preppy, a victim of the organization regime, yes, but he was so much more firmly entrenched in the real world than idyllic, psychotic Smallville. That was good, because not!Smallville was very alluring to her just then.
There was a slight hesitation at the door to Lois's apartment, but before Chloe took it upon herself, Jimmy, emboldened by their deepening affection, kissed her in a way that made her toes curl. Being liked, being wanted, God, it was like a drug. For a millisecond, Chloe thought that maybe she understood Lana Lang. It passed quickly, because it wasn't just being liked, it was him, being liked by him was something special, because he was smart and ambitious and wonderful and if he liked her, then maybe she was a little bit wonderful too.
They were officially together then and they fought and they snogged and did all those couple things. The fights were about stupid things, except for the one time that she'd abandoned him at a club. He couldn't accept her excuse, and she couldn't tell him the truth. He let it go a few days later and Chloe thanked him for it.
She tried not to think about what was going to happen when the summer was over and she had to go back to her life. Three hours away meant phone calls and emails and only seeing each other on weekends when schoolwork happened to be light. Three hours away was long distance enough to mean that it probably wouldn't work. They didn't talk about it, but they both understood.
Chloe's first time was everything and nothing like she thought it would be. There were tangled sheets and heavy breathing, but there was fumbling and near misses, and she giggled once and she didn't think that was the reaction Jimmy'd been going for. It hurt less than she'd heard, but it didn't feel quite as good as she'd hoped it would. But she smiled, genuinely, because it was still nice, and they were sharing something that she would never forget, and would never want to.
The day she had to go back to Smallville, Chloe felt like curling up into a ball and sobbing for a few hours. Back there was everything that she wanted so desperately to escape from, things she had no desire to deal with and things that she was not sure if she could handle. Back there was no Jimmy to be a bright spot in her screwed up life. She sufficed with a sniffle or two as she lugged her suitcases down the stairs.
Jimmy was late to see her off. He was never late for anything and the reality of her going smacked Chloe in the face all over again. He hugged her and she did cry. Then they kissed, and he tangled his fingers in her hair and she had a death-grip on his shoulders, just wanting him closer to her. People walking down the street paused and stared, and Lois shooed them away. Chloe's nose was red and her lip gloss had worn away when she got into her car. But when she walked back into Smallville, into the Talon, there were a lot of things that she had let go of, and that did make it easier to be there.
One e-mail every day where they only talked about insignificant, normal things was what their relationship came down to. One e-mail and the understood promise of: someday.
He came to her funeral, and he cried. Chloe had never seen him cry before and it broke her heart. The day after Lionel Luthor's trial he e-mailed her. She gave him her new phone number and he called. She explained everything that she could, and realized that she might just love him when he didn't turn tail and run. That was why she knew that eventually he would come to understand why she stopped responding the day after Lionel Luthor was released from prison. Chloe refused to give the devil incarnate someone else to target, someone else's life to destroy. That didn't make it hurt any less when Jimmy stopped trying.
Chloe bore her sorrow with a grin, like always, and didn't talk about it. The first time she thought she might be able to do so honestly, her hopes were dashed by the look on Lana's face, and she knew that the other girl would never understand. So, Chloe lied and told a dismissive story, her good deed for the day, in an attempt to stop Lana from doing something for all the wrong reasons when she obviously found it repugnant to begin with.
Then Chloe sat there in the Torch after Lana had run off to do it anyway, refrained from writing to him right then, and hoped that "someday" would wait a little longer before it transformed into "never."