Okay. SO! Would def at least somewhat know Addi & Kenzie from High School. Possibly Liv too, though she would have been a year, maybe two younger.
Kenzie absolutely thought he was an ass and I feel like they would have some snarky banter wherein... she doesn't hate him cause she doesn't hate anyone she just never subscribed to the belief that he was God's gift to anything. Definitely, the ego-check shit calling type.
Addi... Her level of tolerance would greatly depend on whether he were friendly with Gray or not.