Notes:

Jessie model is pretty and her voice is nice so it's easy to find her infatuation for Cloud endearing but from Cloud point of view, I can see this being something between annoying or downright creepy.

Just picture Jessie has an average or below average person and her antics lose lots of the appeal.

Still, she looks good so she gets the good-looking people pass which is being able to act whatever and get away with it.