10 Most Toxic Hollywood Relationships Ever (5 of 6)

Taylor Swift and Conor Kennedy

We love TSwizzle, but like many people in their early twenties, she’s had at least one relationship that sparked a lot of conversation. In 2012, she briefly dated Conor Kennedy, who was 18 and still finishing high school, while she was 22. The relationship was legal, though the age difference naturally raised eyebrows and prompted mixed reactions. Some observers speculated that the Kennedy legacy played a role in the attraction, especially after reports that she bought a home near the family compound—a move that added fuel to the chatter. Still, it was a short-lived romance during a formative period for both of them, shaped as much by public scrutiny as by youthful curiosity.

OJ Simpson and Nicole Brown

OJ Simpson and Nicole Brown married in 1985 after dating for years and had two children, but the relationship was tarnished by OJ’s abuse. In 1989, OJ Simpson entered a plea of no contest to spousal abuse, while Nicole filed for divorce in 1992. In 1994, she and her friend Ronald Goldman were found murdered, and OJ became the prime suspect. He was acquitted in criminal court but later found liable for their deaths in a civil trial. This one isn’t just “toxic”; it’s downright tragic.