#4: Lindsay Lohan and Samantha Ronson

Duration of Relationship: Around two years (2008–2009)

Lindsay Lohan and DJ Samantha Ronson’s high-profile relationship ended dramatically in 2009 after a rollercoaster romance. Their on-and-off relationship was constantly in the media spotlight, with rumors of heated arguments and emotional outbursts.

Lohan, who was open about her love for Ronson, struggled with the public scrutiny and pressures surrounding their relationship. After a particularly intense argument, Ronson reportedly decided to end things, which led to Lohan’s emotional public breakdown. The split left Lohan devastated, and she later admitted that it was one of the most challenging times in her life.