| Music Video | Middle School Lovin' “Grind Song” |
| Sabrina Carpenter | ... | Caroline |
| Chloe Fineman | ... | girl |
| Marcello Hernández | ... | guy |
| Kenan Thompson | ... | Principal Atkins |
| Bowen Yang | ... | guy |
| Jeremy Culhane | ... | guy |
| Ben Marshall | ... | guy |
| Ashley Padilla | ... | mother |
| Kam Patterson | ... | guy |
| Veronika Slowikowska | ... | girl |
| Jane Wickline | ... | girl |