Ben may be back to his life as Hollywood’s most eligible bachelor, but that doesn’t stop us from taking a look back at some of his most publicized breakups of all time. After spending three years dating Gwyneth Paltrow, Ben later began dating Jennifer Lopez and proposed to the entertainer with a 6.1-carat pink diamond ring in 2002. The couple ultimately called off their engagement a year later.

It was then that the courtship between he and Jennifer Garner began and ultimately evolved into a marriage lasting 10 years. Jennifer and Ben had three children together and later divorced in 2017.