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.