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In my very first game I encountered the same dialogue loop.
1.
I applied the Jaheira patch Zbyszek mentions and reloaded a savegame about one week (game time) old. I just wanted to be sure to fall some romance dialogues back. It worked fine.
2.
If it doesn`t work:
Here is my "cure" for this loop before I learned about the existence of the Jaheira patch.
Use shadowkeeper:
Just to be sure, check the GlobalVariable JaheiraRomanceActive. It must be 1 (you're romancing Jaheira).
Set the GlobalVariable JaheiraRomance to 1 (it should have a pretty high number now). It's a timer, if its value is reached by the internal game timer, the next dialogue should appear.
If you click on Jaheira's portrait (still in shadowkeeper) one of the tabs is called Affects. Open it and look for LOVETALK (it should have a value somewhere near or in the 50s), increase it by one.
That worked for me. After loading the edited savegame the next dialogue popped up immediately.
Some days later, I got really stuck with this romance. I won't describe what happened (it would spoil to much) but this little nasty bug made the game unfinishable.
That was the reason for learning about the Jaheira Patch (stumbled on it by using search engines). I applied it and went back to a savegame before this damned dialogue loop (see 1).
In my recent games - with the patch applied - there were no problems at all. Thus, my general advice: If you want to romance Jaheira, use the patch from Baldurdash.
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