TNG S4E16 Galaxy’s Child
This episode has so much cringe in it.
Geordie setting up a meeting and trying to make it into a date is a lot. Plus omitting that he had the computer summarize her files to resolve a critical crisis, while using the information he got from her file in discussing with her is not good.
Brahms does an excellent job letting him down and putting up firm boundaries.
But oh god, when she discovers the holodeck program, and then Geordie rant!
It’s tough to watch in a totally different way than the Quark Gender swap episode.
You’ve named some strong contenders, but don’t forget the episode where Kes goes into heat