Summary: After all, whenever Oliver knew something that Chloe didn't, she always had the cutest reactions when she figured it out. AKA Five times Oliver knew something Chloe didn't. Season 9 and 10 spoilers
This story is dedicated to
serafina19!
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The first time it happened, they were very close together and she had just hit a practice target with a bulls-eye. He took the bow away from her hand, smiling, and high from the thrill of sharing the adrenaline rush that he felt every night on patrol with her.
There was something about the look of pure joy in her eyes when she turned around to look at him. He spent weeks trying to resist his attraction to her, mostly because he was afraid that it was just him looking for a rebound after Lois rejected him. He didn't want to break Chloe's heart, so he tried to control himself around her. But he saw the look on her face as she turned around to face him. The excitement rushing through her veins, and then the two blinks of her eyes as she saw the uncontrollable lust in his as he noticed the proximity. It was too much for him. He couldn't pull away from her anymore.
He waited, not wanting to push her away. She got closer and closer to him, almost tentatively as she tested the waters. And then her lips touched his, his eyes closing at the contact, his hand dropping the bow in his hand with the sheer shock of it all, that she hadn't made up an excuse and left. The bow made a large clattering sound as it hit the floor. She grabbed his neck and pushed it closer, and he wrapped both arms around her, pulling her up off of the ground, her toes dangling in the air.
It happened a second time when he called up a storage truck and had her Kryptonite weapon stock-pile relocated. He was pissed off as hell at her that she never told him. She asked him where he put them the next morning. The truth was that he had them scattered to secure facilities around the globe. There was also another known truth that he was aware of, and it was that Chloe was Watchtower. She had taken it upon herself to make sure that she knew things before anybody else did. It would have been easy for her to sit down at her desk, start typing on a keyboard, and then magically come up with the locations.
But a funny thing happened instead. She didn't. He had a sneaking suspicion that she knew exactly what actions to carry through with to get the results on her monitors, but she never did. And she never mentioned the weapons. He thought for months that she looked it up, but he came home from a business trip one day to find her scraping away at a branded mark on the wall. She said that Clark found them, and swore up and down that she never even looked for them once.
He believed her. Because the look in her eyes told him everything- the sheer terror in them at the possibility of him assuming that she went behind his back again.
The third time it happened, he was nervous. Because she swore up and down to Lois just that morning that they were keeping things casual, and Clark convinced him that he better not be a complete and total jackass to her after she had jump-started his life. He went to the gift-shop, picked out the first thing that he saw in case she caught him in the act, and bought it. He spent three minutes flat in that store, and then darted upstairs to the room and stared at the little wrapped box for what felt like hours before leaving it on the bed.
She wanted to go upstairs to catch up on some sleep before dinner, but he stopped her, and said that if they had an early dinner, it would be a meal spared from the awkwardness of Lois and Clark. She shrugged and agreed. She probably thought that they were just having a good old time, enjoying dinner and drinking glass after glass of wine. He kept pouring glasses for himself to calm his unnaturally nervous feelings, and poured glasses for her to keep dinner going.
The truth was that he dreaded what her reaction would be, because he knew that she would overreact. And she did, right on cue. But not because he bought the present, she seemed to be okay with it at first. And then she flipped the box over, saw the sticker of the Inn they were staying at, and knew that he bought it earlier after speaking with Clark.
She pawned it off on the rules, but he knew the truth. She was mad because Clark convinced him. That he hadn't done it himself without an added force.
The fourth time it happened, she took his hand and dragged him back to the Watchtower after they had taken turns (unintentionally, mind you) being kidnapped over a time span of two days. They were mutually terrified of the idea of losing each other, and practically had sex in the elevators, they needed to be together so badly. He realized it when the elevators doors opened and they were naked. He got up really quickly, scooped their clothing up, and offered a hand to pull her up before opening the doors for her.
He needed to scoop up their clothes and open the doors to busy himself before he said the words right there and then. Because in that moment, he realized that he was in love with Chloe Sullivan, and she wouldn't like it at all. She would call it a slippery slope, and he would never see her again.
He made plans to leave town that weekend on business to keep the information to himself so that he wouldn't lose her. Became very busy very quickly. But he couldn't stay away for longer than a week or two, and definitely couldn't go without talking to her for more than a couple of hours. With every text, he had to control himself, and with every video chat, he needed to stop the words from tumbling out.
He came back home just to talk to her, but Clark came to his office twenty minutes after his jet landed, and the next thing he knew, he was in his gear at Luthor Mansion trying to track down Zod. He ended up getting a Kryptonian symbol branded on his body instead, and winding up in a hospital. Not exactly his idea of a rooftop picnic with the sunrise.
He was airlifted into Star City to get plastic surgery after he woke up. Not because he wanted to get airlifted into Star City, but because he was in a hospital when he finally saw Chloe sleeping in a very uncomfortable chair holding his hand when he did wake up. He gave her hand a little squeeze, and she jolted up, apologizing for drifting off for a couple of minutes.
He wanted to say the words then, but realized that her brain was working so hard, she could probably churn butter in there. He asked what was wrong, and she told him about her day.
She said that Tess broke into Watchtower and Checkmate almost killed them both. She said that to escape, she needed to crash Watchtower's system, and that Tess knew about both of their secrets, probably even the whole team.
He wanted her to be as calm as possible when he finally told her that he loved her. Now wasn't the time.
They prepared for the end of the world, he went to rally up the troops and make sure that his business was okay, when he decided to video chat her from the jet. She was working at the Watchtower in green leather, and he wanted to tell her then. But he figured that somehow, they would have time, that for some reason, they had all of the time in the world. And that the right time needed to be in person.
But when the right time actually came around, he couldn't see her face at all. It wasn't via webcam, and it wasn't in a time of calm in their lives. It wasn't after they had sex, and it wasn't even one of the many speeches that he had prepared beforehand.
It wasn't traditional at all, but her reaction was beautiful nonetheless. Not even a moment's hesitation on that walkie-talkie as he crawled through an air-vent because his life depended on it. There wasn't any static, and there wasn't any confusion flying in her head.
He said that he loved her, and she said that she loved him back.
The fifth time it happened, he spent the entire day looking for the engagement ring of his ex-girlfriend instead of looking for Chloe. He felt stupid the entire time, and it wasn't until he removed the makeup that for some reason he needed to wear (all the while reminding himself that he spent years as a billionaire playboy and recently monogamously making love to a beautiful woman, so he could be confident in his sexuality and masculinity), and changed from sequins to the pants he was wearing before that he pulled out the marriage license in his pocket and saw that it was ripped in two.
He didn't need to know what happened to the other half. All he knew was that two days prior to Clark and Lois' engagement party, he received a voicemail from the Star City Register, asking for a job reference for a Miss Chloe Sullivan. The nervous, squeaky voiced woman said that normally, she would ask for a recommendation from someone in a lower position, but her resume said that she worked directly for him.
He knew that she was leaving, and that even in the most drunken state imaginable, he wasn't going to let her leave. She was the only one who could make him fully commit to a relationship even if it wasn't originally in the Chloe Sullivan plan.
He said before when she finally accepted their relationship that just being his girlfriend was incredibly high school-ish. That it seemed a bit degrading to their relationship since they both sacrificed their own lives to guarantee the other's safety. He turned off the communications before getting kidnapped so that the signals wouldn't lead back to her, and she traded her life for his own.
He married her, and she agreed. And Lois said that she wouldn't bet her own engagement ring unless she knew she would win. He knew once he saw that ripped piece of paper that he didn't wake up on a railroad track next to Lois because they did anything.
He didn't have his company, his accounts were frozen, and he wanted to give Chloe a real engagement ring. The only person out of their group who would have gone with his insane plan of gambling was the kooky cousin of the woman that he was in love with.
When everyone was okay, safe, and accounted for, he wanted so much to tell her what had really happened the night before.
After all, whenever Oliver knew something that Chloe didn't, she always had the cutest reactions when she figured it out.
She had the other half of the marriage license in the end. She knew that there was one, and the second she saw his half, he looked at her intently to get the reaction that he was looking for.
And it was there. Tears automatically pooled in her eyes, and she looked up, as in silently asking him if it was real. She pulled her own half out of her pocket and joined the two halves together.
They were two halves before they finally found each other, lost and wandering aimlessly throughout the world, looking for a deeper purpose. And when the two halves of the marriage certificate united, so did Chloe Sullivan and Oliver Queen.