In the bizarre world of celebrity dating, you might see more highs and lows than a bustling list of sweepstakes casinos, however, today we will be exploring seven of the worst celebrity matchups where the best throw of the dating dice was to throw them away. So sit back, relax and get yourself comfy as we take you on a trip down memory lane. Here are our top seven list of the worst celebrity matchups.
7. Taylor Swift and Tom Hiddleston
There isn’t a celebrity on planet Earth who has had more publicised relationships than Taylor Swift and whilst she now enjoys a wholesome dating life with NFL star Travis Kelce, it hasn’t always been plain sailing. British actor Tom Hiddleston enjoyed a brief romance with the superstar singer which many believed to be a publicity stunt to divert attention away from her ongoing feud with Kanye West, it’s safe to say this one didn’t last very long.
6. Mariah Carey and James Packer
Messy and abrupt are two keywords to describe the celebrity engagement of Mariah Carey and James Packer. The couple’s larger-than-life personalities and lavish lifestyles ultimately brought an end to their whirlwind romance in true Mariah style. It’s safe to say, Carey doesn’t want Packer for Christmas anytime soon.
5. Tom Cruise and Katie Holmes
Tom Cruise and Katie Holmes’ romance had everything you would want from a true Hollywood relationship and their marriage raised huge eyebrows with the tabloids in the United States and beyond. Many speculated that Holmes was pressured into the marriage with Cruise due to the actor’s involvement with Scientology, although, this has never been confirmed or denied.
4. Madonna and Guy Ritchie
This one was a strange matchup from the start and their extremely different backgrounds and interests eventually led to a high-profile divorce and custody battle over their children.
3. Jennifer Lopez and Casper Smart
Lopez and Smart’s relationship started when Smart was a backup dancer for the hugely famous singer, however, no one backed the backup dancer to keep Lopez’s heart for long. In 2014 the pair called it quits after about two and a half years together. There were claims that Smart wasn’t so clever and cheated on Lopez throughout their relationship. Silly boy.
2. Kim Kardashian and Kris Humphries
In true Kim Kardashian style, their highly-publicized wedding lasted a grand total of 72 days before they both filed for divorce. Tabloids and fans of the reality star went wild with accusations the whole marriage was simply a publicity stunt rather than a genuine relationship, something Kardashian has firmly denied.
1. Britney Spears and Kevin Federline
Drama and controversy filled this celebrity matchup from the very beginning and their tumultuous relationship played out in the media for the public to see. It all ended in tears with a messy divorce and custody battle for the pair’s children. Despite this relationship ending years ago now, the pair are still bickering over child support payments in 2023.