It took Dick quite a while to open up enough emotionally to admit he was interested in her properly. It wasn't until after the Blackfire/Citadel War arc that he admitted to himself how much she meant, and they started dating properly.
Also slightly complicated by the Dala and the Monk arc over in the Bat-titles which was running concurrently. Being vampirised into a by a woman you thought you loved might make you a little over-cautious.