In retrospect, Barbara knows that things between them will probably never work out. She has long been over the age difference; really, five years is next to nothing when you're in your twenties. But, regardless of their age difference, they had other issues.
She had, for one, refused two separate proposals of marriage from him. It wasn't that she didn't want to marry him, but the first time she hadn't been ready, and the second time, he hadn't been. She didn't really know where she stood on the issue at present, but she does know that she loves him, in spite of all the reasons she has that she shouldn't.
One of her big things had been the chair. It was an obstacle, and maybe he didn't see it as such, but she surely did. He loved her as Barbara, his Babs, not as Batgirl or Oracle. Whether or not she could use her legs was not something he seemed bother by, but it caused problems for her. She knew he loved her, but somehow, she always managed to question it.
Sometimes, she wonders if he's really as committed to her as he says he is. Sure, he loves her, and she mostly believes that, but does he love her enough? Does he really mean that he wants to spend the entire rest of his life with her? Surely he cannot stay settled down with one person for so long.
But Barbara understands this, understands him. Born and raised a performer, he craves attention. He has always, as long as she has known him, been on the move, whether it be physically or not. He gets bored easily, and she knows this as well as she knows that Bruce is going to be patrolling Gotham until the very day he dies. Dick needs to move, and Barbara understands this.
And so she pushes him away more often than she wants. It is almost habit by now. She loves him, and she doesn't want to get hurt. She doesn't want him to be hurt either, though she knows that she does sometimes. Every time it happens, she says a silent apology, knowing that she cant say it out loud. Neither of them are ready for that kind of commitment, and she knows that if she shows remorse he will pounce, ring and license in hand. And she knows that she cannot refuse him a third time.
In the long run, she knows she would be happy with him, but she often wonders if they could last. He was a vigilante, and she knew, perhaps better than anyone else, that associations with the protects of the night can easily be tracked down and hurt. She has the bullet wound and the inability to use her legs to prove it. Marriage to Dick Grayson was one thing, but marriage to Nightwing was another, and Barbara knew that there was no separating the two, much like she could not divorce Oracle from herself. Though she often imagined Barbara's wedding to Richard, she could never imagine Oracle's to Nightwing. And how were they to make a marriage work if their other halves weren't just as united?
So, sighing, Oracle wheeled herself back towards her console, thoughts of Dick Grayson and all he meant to her still on her mind. She idly wonders if Dick ever thinks of their relationship as she does, and even goes so far as to think that he probably knows that she isn't sure about spending the rest of her life with him.
She then and there decides that she will have a conversation with him on the matter, get his opinion on things. Set the record straight. Because Barbara knows one thing for certain – she loves Richard Grayson, and she thinks that he needs to know it. Regardless of the consequences and the fact that she is sure that Dick has a ring on him at all times, ready to pounce at the first sign of weakness.
She smiled at the thought, though it scared her a little. Yes, she'd have a conversation with him. And she would take the repercussions of that conversation, no matter what they may be. And if she ended up with a ring on her finger, she decides that it wouldn't be such a bad thing.