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Your character should have domineering on the crew,  meaning you should have higher honor points on the crew and sithyrya. Arouse him (and defeat him sexually) in the prior combat (comet arc), training combat for the first time (before fighting the big baddie in the sithyrya), and also humiliate him in the club (akra) when you are doing the waitress/waiter job. Your character kink MUST be also dominant and top.

Note: if you did not do it for the first time, you can't change it no more again, unless you have the patreon ver or savescum the prior event to restart it.