An aging noblewoman values her privacy. It's a question of how much benefit you can gain from either overriding her will or playing on her insecurities.
Delenda will be at 18 in the third level of the Three Old Kegs. Talking to her and refusing to leave, talking to her multiple times, or talking to her but staying in her room for too long are all reliable ways to get her to shout out loud to summon her bodyguard, Bartleby.
Threatening Bartleby will result in him backing down, and both Delenda and himself leaving. That results in a 200xp reward.
Agreeing to leave the room and avoiding violence results in no rewards at all.
You can provoke Bartleby into attacking you. He'll leave behind Bartleby's Wakizashi +1 should you defeat him. But Ithtyl Calantryn will teleport in and demand to know what the commotion was about. You'll lose -1 Reputation if you choose any other reply besides that Bartleby attacked you. You'll still lose -1 reputation if you did claim that Bartleby attacked you but fail a Charisma check of 12.
If your Hero of Baldur's Gate is a Mage, he or she can flatter Delenda with the offer of a magic spell that will smooth out her character lines overnight. Failing a Charisma check of 12 results in her calling for Bartleby. Making the check convinces her to willingly give you her Laeral's Tears necklace.
If your Hero of Baldur's Gate is a Bard, he or she can flatter Delenda on her 'beauty', and then offer to inscribe a love poem on her Laeral's Tear necklace. Failing a Charisma check of 12 results in her calling for Bartleby. Making the check convinces her to willingly give you her Laeral's Tears necklace.
Casting a Charm Person spell on her, and with her failing her saving throw, turns her circle green. "Force-talking" her then opens up a different branch of possibilities.
Asking her about Caelar gets her to reveal information about her lieutenant, Hephernaan. This is helpful but not required for purposes of the Important Events Quest.
Asking her directly for her Laeral's Tears necklace will result in her calling in Bartleby.
Selecting the dialogue option that you've fallen on hard times will give you a chance of getting the necklace. Making a Strength check of 16 while telling her to "hand it over" will result in getting the Laeral's Tear necklace and 500xp. Failing the Strength check will have her calling Bartleby in.
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