Bad Calls: Horrible Dating Choices Your Favorite Celebrities Probably Regret

- By Bossip Staff Categories: Break Ups, Coupled Up, matrimony-dom
Janet Jackson Jermaine Dupri

Celebrity Relationships They Probably Regret

We all make relationship mistakes. We all date people that we totally regret ever having been with. It happens all the time. However these bad relationships linger with celebrities forever as we always remember the pics and bad decisions. These poor celebs made horrible dating choices and we won't forget them. Let's look at some regrettable dating decisions these celebrities made.
Deelishis - Even though she did it for a reality show, she let Flavor Flav chop her down.
Sandra Bullock - You think she's pumped about her sorry relationship with dirty dog Jesse James? Of course she does.
Britney Spears and Kevin Federline arrive at the 2006 Grammy Nominees Britney Spears - Kevin Federline damn near ruined her life. And everyone told her not to do it.
janet jackson and jermaine dupri Janet Jackson - That Jermaine Dupri move wasn't great for her. He has that huge tattoo of her too. Awkward.
Drake - We wouldn't say him dating Dollicia Bryan was a bad choice. But the whole public announcement followed by a break-up the next day over contacts was quite the embarrassment.
Lauren London and Malika Haqq Lauren London - She got her ovaries invaded by Lil Wayne! WEEZY! Nooooooo!!!!
mariah carey Mariah Carey - The relationship with Eminem was less than healthy and made Nick Cannon start rapping again. That's a loss for everyone.
Angelina Jolie and Billy Bob Thornton at the London premiere of Tomb Raider Angelina Jolie - She was married to Billy Bob Thornton...that was not up to par. And the way she loved that man? Bizarre.
Katy Perry - She married oddly-shaped annoying Russell Brand. THEN she went on to date John Mayer. What is she thinking?

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