The first couple on the list is one that was most famous for being such a friggin’ disaster. English singer and perennial bad boy Pete Doherty and Kate Moss were in the British tabloids for years for being a) an unlikely pair and b) trashbags.
These two dated on and off for a few years before finally breaking up in 2007, mercifully not bringing any children into the world.
You’ll no doubt remember this couple for their Golden Globe winning reality show: Britney & Kevin: Chaotic (ed. Note: THIS SHOW WAS NOT NOMINATED FOR ANYTHING EVER, NO WAY). Britney Spears, pop sensation and proud supporter of rage-based haircuts, married former dancer and professional wrestler (I SWEAR TO RIC FLAIR) Kevin Federline and had what no one called a whirlwind romance for the ages.
The couple split but at least they got two pretty cute sons out of the whole deal.
Russell Simmons dated German supermodel Hana Nitsche in ‘12, but the couple broke up less than a year later in ‘13. Most people probably best remember Simmons for his 11 year marriage to Kimora Lee and wearing a fitted Yankees cap with everything because, trademark look.
While Simmons was dating Nitsche in 2012, Lee would often vacation with them because going on vacation with your ex is totally normal and of course won’t place any strain on your relationship at all at all.
American Idol judge and British-Alan-Thicke-covered-in-sunburnt-calluses, Simon Cowell dated 90s bombshell Carmen Electra when the two met on Britain’s Got Talent.
Their relationship lasted two months and ended when Electra caught Cowell with Lauren Silverman, another woman with bad taste in bed. Silverman would later carry Cowell’s seed and bear for him a son.
When Jessica Alba married some dumbhead named Cash in 2008, folks around the globe were a bit puzzled. No one really knew who Cash Warren was, no one knew why anyone would name their child Cash, and no one knew why a grown man, with autonomy and freedom of choice, would still opt to present himself to the world as “Cash”.
Regardless, they dated, got married, have two daughters named Sixpence and Nickels, and a newborn son.
Michael Jackson met Lisa Marie Presley (best thing to come out of Elvis in ’68) in 1975 but the two didn’t start “dating” until the early 90s. They married in 1994 but divorced only two years later, probably, well, because, you know. I mean come on, Michael Jackson.
Dennis Rodman and Madonna were really hot and heavy for an action-packed two months in 1994 before calling it quits. Rodman, in his autobiography, and clearly without any pretension or ego, stated that “Madonna wanted to have my babies” but left out the part where she dumped him upon realizing he was not, as she once believed, Wesley Snipes in Demolition Man.
Katy Perry and Russell Brand married in 2010. They had a traditional Hindu ceremony in Rajasthan, (OF COURSE THEY WOULD – INSERT GROANS AND EYE ROLL, PLEASE) but divorced in 2012. Perry claims that Brand had told her he was filing for divorce via text message, and then straight up ghosted her. This is totally not fitting some of Brand’s views on religion.
Courtney Love and Edward Norton met on the set of 1996’s The People vs. Larry Flynt (WOODY HARRELSON, I GOT YOU, BABY!!!!) and began dating shortly thereafter. The couple remained together until 1999 when they broke up because Love decided to leave him for some jabrone who ended up stealing all her money. Edwards is said to have consoled himself by preparing for the new millennium WILLENNIUM, blasting the now-classic Will Smith jams, Wild Wild West and Will 2K.
Colin Farrell, man who inexplicably continues to wear two earrings and a goatee, told Ellen Degeneres (and about a million folks watching at home) that he had a brief affair with Elizabeth Taylor before she passed away, although he admitted it was never consummated.
If that counts as a relationship, then from 1992-2012 Cindy Crawford and I were married.
Chag Kroeger and Avril Lavigne, the great shames of Canada, started dating in 2012, compassionately taking each other off the market. They began dating after working on Avril Lavigne’s fifth album together – because two grown people writing songs that would be embarrassing if sung by a 16 year old is super romantic and how all great love stories start. They got married in France in 2013 (their marriage was illegal in Canada) but split in 2015 because Kroeger had “to go and make everything so complicated”.
In September of 2006, before Nick Cannon miraculously met and married DIVA (ALL CAPS) Mariah Carey, and somehow came out on top in the divorce and in the court of public opinion, he briefly dated Kim Kardashian, now Kardashian-West and the reason your daughter no longer thinks math or science is important.
Cannon admitted that he and Kardashian broke up because she had lied to him about the sex tape she later used to launch her ridiculous empire.
Actor, musician, and pretentious weirdo Jared Leto began dating the number 1 best Charlie’s Angel (I DON’T CARE WHAT YOU HAVE TO SAY ABOUT IT) Cameron Diaz in 1999 and even proposed to her in 2000 (AKA THE WILLENNIUM).
The pair broke up after a four year relationship because they wanted to focus on their respective careers, or in Leto’s case, pretending to be the characters he plays 98% longer than he needs to.
Madonna (yup, she’s on here more than once) and one of the DIY Network’s breakout stars of 2009, Vanilla Ice dated for eight magical months in 1990 before Mr. Vanilla ended their relationship (yes, he left her).
The unsung gem of TMNT II: The Secret of the Ooze revealed that Madonna’s reputation as a sexpot harlot was the reason he left her. Continuing his trend of excellent decision making, he then went on to star in the 1991 flop Cool as Ice.
Carmen Electra married best-friend-to-celebrity-dictator-Kim Jong-Un, Dennis Rodman in 1998 in a super classy Las Vegas chapel, but following months of tumult and chaos, the two broke up. Electra confessed that she started dating Rodman after her mother passed away from a brain tumor, and surprisingly not because she had one herself.
Famous butt cheeks Kim Kardashian and human-shaped corndog Nick Lachey briefly dated in 2006 after Lachey’s highly publicized divorce from July 2006 Maxim cover model Jessica Simpson.
Lachey has suggested that Kim used him to get famous: “Let’s just say this: We went to a movie. No one followed us there. Somehow, mysteriously, when we left, there were 30 photographers waiting outside,” he said.
Ryan Gosling and Sandra Bullock were co-stars in the 2002 movie Murder By Numbers and began dating as filming wrapped. The couple ultimately only dated from 2002 to 2003 and eventually broke up. Gosling found love (and a baby) with actress Eva Mendes while Sandra Bullock ended up married to redneck cold sore Jesse James.
Most people don’t know that Drew Barrymore and the former Mr. Courtney Cox, David Arquette secretly dated (most people also do not give a fart).
The pair played brother and sister in 1999’s best movie: Never Been Kissed (NO BS, THIS MOVIE IS MY S#!T) “She’s just one of the sweetest, kindest people in Hollywood. We used to run around and just be silly,” Arquette said about her. Because, as everyone knows, the best thing to base your relationships on is silliness.
Courtney Cox dated THE BEST BATMAN OF ALL TIME, Michael Keaton, for six years before they split up in 1995. So to be clear, she went from being called up on stage by THE BOSS himself, teaming up with He-Man to save the universe, dating BATMAN for more than half a decade, only to end up with the star of See Spot Run and Ready to Rumble (ALTHOUGH SHOUT OUT SCOTT CAAN, OLIVER PLATT, AND DDP)…
Iron Man himself, Robert Downey Jr. and Sarah Jessica Parker (you were my girl in FLIGHT OF THE NAVIGATOR) were in a super serious relationship from ’84 to ’91, only breaking up because of chronic drug abuse. I guess there are only so many times you can wake up in a bed full of Quaalude-induced diarrhea before something has to give.
The two eventually made peace with each other, in 2015, 24 years after calling it quits.
Celeb-shoplifter Winona Ryder and Ben Affleck’s ex-girlfriend Matt Damon dated for nearly two years at the start of the Willenium (aka the year 2000, in case you haven’t picked up on that yet). Their relationship was a secret during the bulk of their courtship.
Damon said, in a quote that sounds like your mom is forcing you to say something nice about a cousin you just got into an argument with at a family picnic: “My most recent relationships have not been with famous women, but I was with a very famous woman, Winona Ryder, for a couple of years, and we had a great relationship.”
Ryan Reynolds and fellow-Canadian Alanis Morissette met at a birthday party for Drew Barrymore, a non-Canadian and obvious hoser, in 2002. They began dating and even got engaged in 2004.
After a lengthy engagement, the couple decided to call it quits in 2007.
Morissette’s album Flavors of Entanglement is about the relationship and the resulting breakup.
Under Canadian law, if the couple remained together for just 11 more months, Tim Horton’s would have been forced to create a donut in their honour (NOTE THE “U” IN HONOUR BECAUSE IT’S CANADIAN).
It may surprise you to learn that Natalie Portman and Moby dated, albeit briefly back in 2001. As a nerd myself, I can tell you, it’s gotta be a pretty big deal to date Luke and Leia’s mom.
America’s sweetheart Julia Roberts and Kiefer Sutherland (aka THE KEIF) met in 1990 when they co-starred in the cult-classic film The Flatliners.
The couple got engaged a few months later and had planned to wed in June of 1991.
Julia Roberts, pure sunlight shaped like the most beautiful woman who ever lived, broke off the engagement just three days before the wedding because Sutherland humped a stripper.
Please note, if you’re ever lucky enough to date FRIGGIN’ JULIA FRIGGIN’ ROBERTS, don’t put your little kief in a stripper. In other words, don’t “flatline” your relationship lolololololololololololllllllllll
Before they both became huge stars (one more so than the other), Juliette Lewis (what heroin would look like if it weren’t so bad for you) and Brad Pitt (a more handsome but slightly smellier Matthew McConaughey) dated for three years between ’90 and ’93 and even starred together in the film Kalifornia (SHOUT OUT MICHELLE FORBES. I SEE YOU ON BSG, BABY!!!!)