Harvey Dent asks her for a date not long after she moves to Gotham. Chloe is the new girl in town, lead reporter for the Gotham Gazette after Bruce Wayne's purchase of the paper gives it an insanely large budget. After breaking off her engagement with Jimmy, Chloe has mostly given up on dating. Harvey is so charming that she can't bring herself to turn him down.
They go out together a few times, and they have fun. He reminds her of Ollie, a little bit, without the parental issues and the insanely large trust fund. After five or six dates, they decide that the spark just isn't there, and agree to be friends.
All the same, when she casts her vote on Election Day, Chloe votes for Harvey Dent. She believes in him, and she casts aside journalistic impartiality after Harvey's declared Gotham's new District Attorney.
Chloe is out of town on assignment when the Joker first strikes in Gotham. She finishes her story as soon as she can, and runs to the airport to grab the first flight back home.
Her first flight is delayed, and on the next, she doesn't even show up on the manifest. Crisis after crisis keeps her from getting home, and it doesn't take long at all for her to realize what's behind the delays.
After she screams at Ollie on the phone for thirty minutes, Clark shows up at the airport, armed with knockout drops. She wakes up in the Fortress days later, imprisoned by her well meaning friends.
Chloe's heart breaks as she watches the city be torn apart on CNN. The Justice League has the best of intentions, but keeping her away when she could help those who are dying is something she'll never quite get over, no matter how long she lives.
After her return to Gotham, one of Chloe's first assignments is an interview with the new Police Commissioner, Jim Gordon. He's a hard man to track down, and with a bit of shame, she finally bribes her way into the Gordon household with a box of pastries from Panera. Donuts and cops would be too cliché.
Gordon has to keep on running out to take calls during the interview, but his young daughter Barbara is in the kitchen, working on a laptop.
"That's a nice computer."
"Thanks. I love computers. They're like the most awesome things, ever. Do you like computers?"
Chloe nods, thinking of the heavy duty hacking she'd done for the Justice League last night, breaking into some heavily encoded files in a Lexcorp Database.
Barbara smiles before changing the subject abruptly as only a little child can do. "Are you going to ask my Daddy about Batman?"
Chloe pauses for a second before answering. "It's my job to ask your Dad about his job, and dealing with Batman is part of his job, isn't it?"
Barbara nods. "He's not as bad as they say he is."
"Batman saved us. There was this guy, with like half a face. He was gonna shoot us, my Mom and my brother and me, and he was really angry. Batman stopped him. He didn't do all those things they say on TV. It was the guy with half a face, I know it! Or maybe it was that scary clown…"
"Babs," Gordon says coming into the room, "What an imagination you have. Let's not bother Ms. Sullivan with stories. We've got an interview to do. Chloe, thank you for your patience."
The rest of the interview goes smoothly, but Barbara's words continue to echo in Chloe's brain.
"What IS this?" A deep voice growls out of the depth of a dark, Gotham night. "Facts are facts. I'm not some cuddly super hero like they grow in Metropolis."
Chloe jumps at the sound of his voice. Clark could totally take tips from Batman on being stealthy. Even though he can fly, Clark still has the subtlety of a freight train. "You've done your research."
"I like to know what goes on in my city."
"Seems like we're both on a quest for the truth." Chloe shrugs.
"This isn't the truth."
"It depends on your point of view. Many of the truths that we hold dear actually depend on what point of…"
"Spare me the Star Wars lecture." It almost seems as if Batman was rolling his eyes.
"Whatever." Chloe grabs the newspaper out of Batman's hands. "I wrote what I saw to be true. I don't really believe all that they say about you. Why would someone who has gone out of his way not to kill someone in the past suddenly cross a line? Obviously there's some reason behind the whole image makeover, and I'm not going to try to kill that."
"Then why did you write the article?"
"Because I did my homework. Because no matter what, I believe that you're someone who wants the best for this city. I believe in you." She paused slightly. "And believe me, I'm no stranger to vigilantes." Chloe looked down at her watch. "Now, if you'll excuse me, I've got a train to catch."
This will not be Chloe's last encounter with the Batman.
Her article, "I Believe In Batman" will win her a Pulitzer.