Are you a twitch streamer then? Or was there some big event?

If your character would react to something that has occurred, then there's no reason why not too.
A lot of conversations aren't linear as well. A lot tend to be circular, talking about one point and then bringing up a previous thing, or returning from a tangent.

If you really don't want to have them respond to it (being saying that Annie has a lot of shows in may, a bit more out of foolish confusion), then they could simply be frustrated & move on silently.