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Hi Marlowe!

Warren will have three topics available from the start of the game--the clothes he sells, his hobby and his past during the war--so I'm assuming you're talking about Atalia.

Atalia is a little slower to open up to you.  You will need to discuss the two initial topics available--where she learned magic and what she does outside of work--at least once each before her third conversation topic become available.

As with all NPCs available for conversation, you will only be able to choose one topic per day.  If you choose a unique topic and converse with them every day for three days, the option to confess your feelings will become available on the forth.

Hope this clears up your question!