Hello! I'm Hayley (girlnumber20) and I have Tracey Dawes (shipthis) plus this sorry loser.
I think that Tracey is the most likely to have plot, given that she's slightly older than Kirby and graduated class of '63. She's pretty 'taking care of business' but is okay to chat with. Her mother is the recently retired captain of the Cuba Libre so she is a legacy brat etc.
Dante probably knows of Kirby given that her good friend and her (very much not good friend) ex are on the Whiskey Sour. If you ever hear Liam calling someone "the evil succubus," that's her ^^