#27: Ben Affleck and Jennifer Lopez

Duration of Relationship: 2 years (2002–2004) and 3 years (2021-2024)

There’s almost too much to cover when it comes to Jennifer Lopez and Ben Affleck. Their romantic relationship began in 2002 and ended only two years later, in 2004, with a called-off engagement. They both moved on with different people, resulting in families made as time passed.

However, in 2021, it seemed as though “Bennifer” were finding their way back to one another, shocking fans worldwide with their reunion. By April 2022, the pair will be engaged for the second time. Sadly, though, in August 2024, Jlo filed for divorce, bringing this long-winded romance to an end.