All credit given to CyricZ on their great Yakuza Kiwami Guide on GameFaqs.
Rina is the hostess at Shine. She became a hostess to be around cute girls and it turns out she actually prefers the company of women. Why she'd spend her day talking to men is a bit of a mystery, but maybe Kiryu can figure it out.
Rank Topics
F Rank - Are you new here? -> You look happy.
E Rank - That's not really cheating. -> They're so progressive overseas.
D Rank - Go out with a guy. -> You don't like yourself.
C Rank - Either -> Am I cute?
B Rank - Don't be ridiculous. -> What about adoption?
A Rank - Of course. -> Is there someone in particular?
General Topics
Buying a camera - You gotta spend it to make it.
Trying out different restaurants - Somewhere with tasty ramen.
Karaoke - He ought to sing current songs.
Idol Fan - It's nice that you can get so close.
Christmas Crowds - I don't like crowds either.
Forgetfulness - It's the thought that counts.
Saying Dirty Things - Respond with pervy jokes.
Maid - Do you want me to help?
Host Clubs - How about at okama bars?
Gaining Weight - It's better to be fat.
Events
D Rank - Nakamichi St. near Club SEGA.
B Rank - Nakamichi St. near Don Quijote.
S Rank - After getting the text, head to Cafe Alps, and then Millenium Tower. Fight the drunk.