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When give the option for these two dialogue options, choose the one that best suits.
You’ll meet Dr Tae Takemi shortly after arriving at Yongen-Jaya. Establishing her as a Confidant will kick off the Death Arcana, and you’ll need a Guts rank 2 in order to get intimate.
When the opportunity comes, make sure you hang out with her and improve the Kindness Rank to 2 and above.
Once you reach Rank 9, there will be an option to determine whether the relationship becomes romantic, or stays friendly.
She presents as a tough teacher early on, but eventually you find out she doubles as a maid.
She’ll ask that you keep her second life secret, and will provide you with her number at school when you raise the alarm of another teacher being potential suspicious. Once you make the first call, talk to her often to improve the relationship.
Reaching Charm Rank 8 unlocks the “Bad Medicine” request.