This probably isn't a hot take or a new idea by any means, but it's been rattling around in my head all day and distracting me from getting any work done on my WIPs so I'm going to get it out there so I can focus on other things.
Here's my thing about 3x09- Oliver, by that time, wasn't the kind to overestimate his own abilities anymore. He'd done so and had it end badly too many times before, so by season 3 I think he had mostly learned to be honest with himself about what he was capable of and what his limitations were. So I don't think, whatever he told the team, that he actually believed he had a chance of defeating Ra's. I think he knew there was no way he could win, but he made the challenge anyway because it wasn't about winning for him, it was about keeping Thea safe.
And I think that's why, before he left, he told Felicity that he loved her. Because he thought he was going to die fighting Ra's Al Ghul. Because he didn't expect to make it back. He told her he loved her because he thought that was the last time he would ever see her and he didn't want to die with her not knowing how he felt, and that is the hill upon which I die.
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