I am of the belief that Dick fell so hard and so fast for Kory, but his fear of abandonment coupled with the fact that she’s from an entirely different planet and the other women in the relationships he’s had have compared him to other men instead of seeing and accepting him for him and that gets in the way of his pursuing a romantic relationship with her. He tried to get ahead of the abandonment in 1x08, by being the one to leave first, but was sucked in again in 1x10. And then learned she was from a different planet. In 2x01 he asks her to come with him to restart the Titans, but she didn’t and I feel like he took it personally. (In spite of doing the exact same thing she did a few episodes earlier). Kory going on her own is explained in more detail (to Dick) in 4x01 when they’re in the RV discussing Conner’s need to stay with Lex. She tells Dick that not knowing where you come from is a painful thing. She’s back with the Titans in 2x05 but he finds out that she’s next in line to rule on her planet. I’m sure he feels she will choose her duty over him and the Titans, which kind of comes to fruition in 2x09, but they’re reunited in 2x13. And S3 she discovers the powers she thought were hers rightfully belong to Komand’r freeing her to stay on Earth. However, the main difference between Kory and the other women in Dick’s life is she understands that neither of them is perfect. She loves him flaws and all and never stays away from him for long. She’s choosing to be by his side, to love and grow with him. He just has to realize that now!
And I really do think that the old team abandoning him the first time he let them down did crazy damage to his self-esteem.
He didn’t think he was a good influence on Rachel and was clearly afraid to open up to Kory. I think in s1 when she had to stop him from punching that guy he assumed she’d call him a psycho and leave. Instead, she offered to help him. She really just accepts him and vice versa.
The trick is getting Dick to realize he actually deserves her and to use his words. He comes across as scared and honestly I get it since people tend to leave.
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