I think Kitty's trying to put on this face of being totally confident about where she's at in life, but eventually that façade needs to fall or she'll drive herself crazy. I would be game for her talking to Olivia about this stuff at some point (and even if Olivia doesn't commiserate, kitty will appreciate the support)
These two haven't interacted much since DOOM plot, so it might be good to have them touch base! I don't think Kitty's told anyone that she went and got a tattoo :| (besides Zach, he knows lol)