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25 Of The Most Regrettable Celebrity Tweets

Fail Whale.

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1. When #Craig #David didn't #quite understand how #best to use #hashtags.

Martin Grimes / Getty


2. When Kanye West reacted maturely to a Jimmy Kimmel sketch.

Chelsea Lauren / Getty/ Twitter

3. When Mary J. Blige overestimated her ability to proof read tweets.

Mireya Acierto / Getty/ Twitter

4. When Katy Perry shared far too much information.

Getty/ Twitter

5. When Lindsay Lohan got her social media accounts confused.

Theo Wargo / NBC / Getty

6. And when she came up with this hilarious April Fools' joke.

Jason Merritt / Getty

7. When Kourtney Kardashian went all David Attenborough on us.

Alexandra Wyman / Getty

8. When Lee Ryan proved himself to be quite the philosopher.

Sean Gallup / Getty

9. And when he expressed his love of writing "story's."

Tim Whitby / Getty

10. And when he had this deep thought.

Gareth Cattermole / Getty

11. When Jaden Smith was inspired by Lee Ryan's way of thinking.

Angela Weiss / Getty

12. When Cher let us in on her struggles with technology...

Frederick M. Brown / Getty

13. ...Especially with Fkn tube & google.

Frederick M. Brown / Getty

14. When Alexa Chung forgot that Twitter IS NOT THE PLACE TO SHARE SEX DREAMS.

Especially when it's with Karl Lagerfeld.
Vittorio Zunino Celotto / Getty/ Twitter

Especially when it's with Karl Lagerfeld.

15. When Susan Boyle's Album party went very, very wrong.

Gareth Cattermole / Getty

16. When Charlie Sheen shared his phone number with the world.

Frederick M. Brown / Getty

17. When Maria Fowler offered her commentary on the 2012 Olympics Opening Ceremony.

Gareth Cattermole / Getty

18. When LeAnn Rimes forgot to keep things positive.

Isaac Brekken / Getty

19. When Nick Cannon shared his interesting parenting techniques.

Theo Wargo / Getty

20. When Kim Kardashian had a brush with politics.

Dimitrios Kambouris / Getty

21. And when she hated breastfeeding.

Dave Kotinsky / Getty

22. When Niall Horan fan-girled over Justin Bieber before he was famous.

Julian Finney / Getty

23. When 50 Cent forgot that Twitter isn't Facebook.

Jamie McCarthy / Getty

24. When Lil Jon decided this was appropriate for social media.

Ethan Miller / Getty

25. And finally, when Jessica Simpson gave us this mental image.

Jamie McCarthy / Getty