How Do I Raise Kiro's Affection

[Mistress X]

and how do I know if it's working? I've been trying every interaction I can access with her and I'm not seeing any progress.

 

[Couch]

Wingman --> Play Straight, Rest until Kiro reappears, repeat.

 

[Nik_van_Rijn]

and how do I know if it's working?

As for this part of your question:

Codex --> Stats --> Encounters. Make sure to have it set to displaying All or Other.