The quest becomes available at 50% friendship or rivalry.
Note: When you start Act 2, you will have both this quest and Isabela's Ongoing Search active if Isabela is at 50% or more friendship/rivalry. Isabela's Ongoing Search will trigger first upon speaking to Isabela. After completing that quest, this one will initiate the next time you speak to her.
Isabela will finish a card game with Merrill and speak to you about her outlook on you thus far. You will get three dialogue options, with the first and third each having the standard Good/Witty/Angry options for answers. The second one, however, will have a Flirt option as the middle option. Note that flirting with Isabela here can initiate a romance.
In a friendship, Isabela will invite Hawke to sit, ordering the Hanged Man's best whiskey for him/her.
- Diplomatic: "Thank you."
- Humorous: "That's not all."
- Aggressive: "Save your money."
She will then comment on how Hawke "doesn't judge people."
- Diplomatic: "How so?"
- Flirt: "Just all right?"
- Aggressive: "I don't need your approval."
Finally, she will talk about how if you were part of her crew, she wouldn't have gotten shipwrecked.
- Diplomatic: "It all worked out."
- Humorous: "I wouldn't bet on it."
- Aggressive: "Don't dwell on the past."
Under a Rivalry, Isabela will be much more catty and wonder why Hawke is visiting her, snarking that there's a "burning orphanage full of children to save."
- Diplomatic: "Is there?"
- Humorous: "Of course!"
- Aggressive: "No."
She'll talk about Hawke missing the joke, and states that he/she needs to learn how to have fun like her.
- Diplomatic: "Life's not all fun and games."
- Humorous: "I enjoy life just fine."
- Aggressive: "I'm not you."
Finally, she'll state that "We're not responsible for anyone but ourselves. You can choose to be free, or you can choose to be saddled with all the world's problems."
- 1: "You're not free."
- 2: "Helping others benefits me."
- 3: "Helping others is rewarding."
Regardless of your choice, she will dismiss your rationale, ending with, "We're done here. Talking to you is exhausting, and not much fun."
If you have a rivalry with Isabela, picking either the humorous or aggressive options for the first 2 steps will net Isabela: rivalry (+15). The final step doesn't appear to have any impact. If on a friendship path: Isabela: rivalry (+15) if you chose the aggressive path on all answers and Isabela: friendship (+20) if you choose all diplomatic and/or humorous dialogue options.
If this quest is completed and Hawke has at least 50% friendship/rivalry with her, Isabela will subsequently show up when she is least expected.