Woa, now just take a look at what gets into Charname's diary (It is not a vewy vewy persunal item, you know). I agree to some extend to what has been said above as it is a projection from your own personal diaries you write a lot of personal stuff in. Some spill their heart into their diaries which keeps their secrets and listens to all the stories, even if nobody else does. Charname's diary doesn't qualify in this respect as mine more reads like a shopping list at worst. I don't know how many of you write personal entries into it, Elmonster style. In most of the quests I do not even bother to read what goes into it more than once, as it is seldom tailored at my character, so this could be a nice break as a one-off event.
Kelsey would be good, but perhaps even someone who doesn't admit too openly to having been won over, but is already reconsidering his/her globals.
If someone who puts his/her life on the line to protect mine cannot write a single message into my notes, I doubt the romance would have gone far anyway, but that is just me.