Casey Affleck & Caylee Cowan Spark Engagement Rumors

Are Casey Affleck, 46, and Caylee Cowan, 23, dropping hints they might be engaged?

Caylee Cowan and Casey Affleck attend the Outside Lands 2022 Music Festival in San Francisco, California

Casey Affleck News, Pictures, and Videos - E! Online

Casey Affleck & Caylee Cowan Spark Engagement Rumors

Casey Affleck, 47, and girlfriend Caylee Cowan, 24, have Thanksgiving Day row

Casey Affleck Picks Up Dunkin' Before Ben, Jennifer Lopez's Wedding

Casey Affleck and Caylee Cowan spark engagement rumors

Casey Affleck, 46, Caught Making Out With 23-Year-Old Actress

Casey Affleck

Casey Affleck & Caylee Cowan Spark Engagement Rumors

Casey Affleck News, Pictures, and Videos - E! Online

Casey Affleck and Caylee Cowan are all over each other and possibly engaged while out for lunch in LA

Casey Affleck and Caylee Cowan Spark Engagement Rumors With Ring

New Couple Alert? Casey Affleck Kisses Caylee Cowan

Casey Affleck and Caylee Cowan Together