Celebrity relationships are so common, that they have their own Wikipedia page. The concept of the Hollywood Marriage began innocently and straightforwardly. It was literally two members of the entertainment elite, deciding to walk down the aisle together. Eventually, it would have a bad connotation. The concept was frequently used to describe a union between two famous folks that ended badly and/or didn't last very long. There are several examples on the Wikipedia page.
To be fair, there's a section on the Hollywood Marriage page for people who have been married for longer than 50 years in case you were afraid VIP love is always fleeting. I propose that we add another section specifically for the most nonsensical notable duos. Until that happens, we're highlighting a few of our favorite random celebrity couples. Oh to be a fly on the shopping carts of these former famous flames as they argue over avocados.
Tom Green and Drew Barrymore
When this unlikely romance blossomed, many people were confused. What they didn't understand, and what most women eventually come to realize is that funny matters. This isn't a comment on anyone's physical appearance, but the media was pretty hard on Tom Green at the time. Drew and Tom "began dating while filming 2000's Charlie's Angels," and married in 2001, per PEOPLE. Tom filed for divorce a year later. They reunited for the first time in two decades on Drew's talk show, in 2021.
Lance Armstrong and Ashley Olsen
The question on our mind is, did Lance Armstrong ride a bicycle built for two when he reportedly dated then-21-year-old Ashley Olsen in 2007? He was 36 and was warned by his friends to skip this rather uneven romance, via E News. In Cycle of Lies: The Fall of Lance Armstrong, author Juliet Macur said his "longtime friend and head of his Livestrong Foundation, John Korioth, 'warned the 36-year-old father of three that his May-December romance could damage his cancer work.'" Lance would later damage his own career when it was revealed he used steroids.
Tom Cruise and Cher
If you believe in life after love, you can certainly believe in the love between Tom Cruise and the iconic goddess that is Cher. According to Cosmopolitan, the two met at Madonna and Sean Penn's wedding in 1985. When they ran into each other again at a White House event, sparks flew. While the two didn't date long, Cher did tell Andy Cohen that Tom was one of her "top five lovers." Surely she meant to say Top Gun lovers?
Seth Macfarlane and Emilia Clarke
The mother of dragons met this family guy in 2012, said E News, but they ended things a year later. Apparently the distance got to them, though why Emilia just didn't hop on a dragon we'll never know. She also didn't appreciate how much their relationship was being scrutinized by others, especially strangers on the street who would frequently give her unsolicited advice.
Carmen Electra and Simon Cowell
In a conversation with Loaded Magazine, by way of the Daily Mail, Carmen Electra revealed in July 2014 that she and Simon Cowell dated from December 2012 to February 2013. "I just thought Simon was so much fun and was so smart and he's really interesting," she told the outlet. They allegedly broke up when Carmen caught Simon in bed with his "then still-married baby mama Lauren Silverman."
Chelsea Handler and 50 Cent
Comedian Chelsea Handler hasn't been shy when it comes to her relationship with rapper 50 Cent. The brutally honest jokester and the candy shop-loving entertainer dated in the early 2010s, reported VIBE. Unfortunately, 50 Cent was still pining for his ex Ciara, who is currently married to Russell Wilson, so things had to end between him and Chelsea. That doesn't stop her from making size jokes about her former fling on stage, which 50 Cent happily shares.
Tom Hiddleston and Taylor Swift
Long before playing the field with Travis Kelce, Taylor Swift stepped out with one of Britain's finest gents. Tom Hiddleston was the bloke after Calvin Harris, and it's safe to say he was low key (Loki) a bit of a rebound. They met while co-hosting the Met Gala in 2016 and danced the night away, via Elle. Tom would later call her charming and amazing during an interview with MTV UK. The two then embarked on a whirlwind romance that took Europe by storm that eventually ended in September 2016.
Kourtney Kardashian and Travis Barker
What do these two have in common? We assume all the small things, and maybe some big things as well. Kourtney Kardashian and Travis Barker getting together was on no one's Bingo card and yet these two wacky kids really seem to love each other. It just goes to show ya, love is unpredictable.