Casey Affleck & Girlfriend Caylee Cowan Step Out for a Grocery Run

Casey Affleck & Girlfriend Caylee Cowan Step Out for a Grocery Run in Studio City: Photo #4784723.

Caylee Cowan Archives, Page 6 of 8

Casey Affleck and Caylee Cowan PDA during visit to grocery store in Studio City.

Casey Affleck & Girlfriend Caylee Cowan Step Out for a Grocery Run in Studio City : r/ThisCelebrity

Caylee Cowan Archives, Page 6 of 8

Casey Affleck and girlfriend Caylee Cowan have row in the street on Thanksgiving Day with actress se

Casey Affleck, 46 and girlfriend Caylee, 24, attend Cannes as she puts on busty display, Celebrity News, Showbiz & TV

Casey Affleck and Caylee Cowan PDA during visit to grocery store in Studio City.

Casey Affleck and Caylee Cowan Out In Malibu

Casey Affleck Kicks Off the Week at Lunch with Girlfriend Caylee Cowan: Photo 4739866, Casey Affleck, Caylee Cowan Photos

Casey Affleck, 47, rocks a casual black look at the amfAR Gala with girlfriend Caylee Cowan, 24

An iconic star and a music exec 40 years her junior, more famous couples with a significant number of years between them, Gallery