There were times when he really hated Clark Kent.
It wasn't often. Not really. Well, maybe more than what was supposed to be acceptable. Clark was a really decent guy, for the most part. He didn't like him when he was on his high horse, acting like the all-knowing jackass that only he could be. When he was the righteous stuck up everyone knew he could be, Oliver really wanted to clock him. He probably would have if it wouldn't have resulted in a few broken fingers, or his hand in the process. Then, whenever he was insecure about the fact he was the only fully fledged power-free human on the team, (not that he would EVER admit that), the dark part of his psyche had a little resentment for the rest of the guys on the team. But the one who took the cake, and the majority of his disdain, was Clark. Clark had these amazing powers that he didn't even want. Waste of talent that one. But the only time he really hated Clark were the times he was reminded that Chloe had spent most of her formative years in love with him.
Chloe had been utterly devoted to Clark but he took no notice because his sights were set on the 'unobtainable' Lana Lang. Clark had put her on a pedestal when they were kids, and never got close enough to change that. It was mostly because of the meteor rock necklace she wore, and Clark's unique allergy to meteor rock. He didn't really understand the attraction to her. Oliver lost his parents when he was a kid, but you didn't see him carting around a piece of the plane that crashed and killed them did you? From what he pieced together from the stories he's heard, he figured that Lana was a relatively nice girl, but she always wanted to be the center of attention. So basically, she was a pretty, kind of morbid, attention whore.
When Lana was taken out of the picture, instead of getting together with Chloe, Clark decides he wants to get with her cousin instead. If that isn't a confidence booster, he didn't know what was. The Sullivan-Lane girls had a lot in common, but Oliver knew now that Chloe was the original, and Lois, as great as she was, was only a reproduction. There were quite a few differnces between the two, but there were many similarities. Both were determined, but Chloe was a bit covert in her determination, while Lois was practically flamboyant in her ways. Lois grew up a military brat and embraced it as much as she could. She was a brassy, grab'm-by-the-balls kind of girl and she obviously liked it like that. Oliver could understand the fascination with Lois. He himself fell for her charms, but there was a point where her brassiness went from endearing to crude – and Lois couldn't tell the difference if her life depended on it.
The issue Oliver had was that because of her continual treatment from Clark always passing her over for her "sister", and then her cousin – her self worth wasn't all that high. It didn't help that about 90% of the guys that ever showed an interest in her only wanted to kill her, or tried to use her to get closer to Lana or Clark. Her marriage to Jimmy was a last ditch attempt at a relatively normal life. That didn't work out obviously – and that was before he was killed. He'd gleaned some of the basics from her; about how whenever she put herself out there all she got was bitter disappointment. Oliver decided a while back that if having all these amazing powers meant that you'd be blind to what is happening, and who is right in front of you, then he wouldn't want them for anything.
Oliver isn't blind. Not at all, he can see her for her, not what she thinks she is. Chloe, she was woman personified. She wasn't an in-your-face type of beauty; she was one you would have to look at often, only to see that beauty grow at each glance. She had curves, and incredible ass, and a smile that would take your breath away. She was stubborn to a fault, and she was extremely guarded with her heart. But her flaws helped make her the woman that he cared so much for. With all of the shit that she's gone through in her life, she deserved so much more than what she'd settled for. Even if she didn't believe it, he knew that she deserved the extraordinary.
He loved Lois, at least at the time he thought he did, but he'd come to realize that he was in love with the idea of Lois. She was a woman who knew what she wanted, and she wasn't afraid to fight for it. She was the glimpse of the normal and mundane, a civilian life, that he could never have in his life. He'd held on to her with both hands, but he'd come to realize that normal wasn't what he wanted. Not anymore. He dealt with aliens, super-powered humans and human experimentations on a daily basis – and that's not even counting his day job.
Oliver wanted someone who would be able to live with the Green Arrow, Oliver Queen persona, and the everyday guy Ollie. Chloe was the one woman that he knew of that could take all the shit from his life and not only deal with it, but she could thrive in it. He wanted someone he could trust explicitly with his high-profile identities, and with his heart and that's why Oliver hated Clark Kent more often that not these days. He'd managed to take this wondrous woman and make her think she wasn't worth as much as anyone else in her life. But that was going to change. He's Oliver Queen for gods' sake. He's dated supermodels, A-List actresses and a despicable number of high profile women, or women in general. He knew without a doubt that none of them could hold a candle to Chloe. She's one of a kind. And he's going to prove it to her.
Now all he needed, was a plan.