I think that Katherine might have, yeah. She knew that Damon was still 'obsessed' with her a hundred and forty-five years later and I don't think she realized how the knowledge that she'd never cared would affect him (Isobel is taken off-guard when Damon basically picks Elena's side over Katherine's and it leads her to the conclusion that Damon is in love with Elena).

Katherine herself has been basically the same person for five hundred years. I'm not sure she realized until "Isobel" and then Damon's speech to 'Elena' that Damon is more flexible in that regard than she is.