The main condition of luring Triss to bed is helping wizards and other scholars in escaping from Novigrad. This ambitious plan can be started with A Matter of Life and Death quest. When miss Merigold invites Geralt to her quarters, you should go there and do everything the girl asks. The mission objective is to lead the alchemist out of Vegelbunds property. The main action will be done on a mask ball. Proper clothing and well-led dialogues will make Triss drink too much. This will give you the opportunity for the first step - kissing the girl. This chance will be shown as a dialogue option.
Further part of the operation will start after eliminating a brutal thug controlling the local criminal element. When Geralt gets him and participate in mandatory audience at the Redanian king's on the ship (A Favor for Radowid), the messenger will give him a letter. After reading it you can complete the Now or Never quest. In that quest Geralt will help wizards escape to Kovir. First decisions don't matter too much, most important decision can be made after finding the road in the sewers and defeating Katakan vampire. After that battle, all the characters important for that quest will reach the harbor and Triss will start saying goodbye to the witcher.
Rejecting sorceress at that point will end the whole subplot, but if Geralt asks Triss to stay with him in Novigrad, interesting dialogue options will be available. In a limited time, you must show your feelings to the girl ("I love you" or ask her for another chance ("Let's try again"). In a short cutscene after the conversation, the ship will sail to Kovir but Merigold will stay with Geralt. Further conversation won't have any big importance. The two will go to a lighthouse where, after a short conversation, they will spend the night together.
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