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    25 Of The Most Regrettable Celebrity Tweets

    Fail Whale.

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

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    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."

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    10. And when he had this deep thought.

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    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...

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    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.

    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.

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    19. When Nick Cannon shared his interesting parenting techniques.

    Theo Wargo / Getty

    20. When Kim Kardashian had a brush with politics.

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    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