The only way it makes sense to me is that it's like everything else about Damian's view of himself--completely disconnected to reality. Like he's talking as if he could actually date this woman and wants to, but really it's just insane, like an extreme form of pretend. Like him saying he could be Batman now. Like he thinks he's sounding grown-up but really he's just showing he's a child.
I mean, I can easily imagine Dick developing a crush at this age--but he would have done it in an age appropriate way.