Top 10 Tech Embarrassments You'll Want to Avoid

"Halfway through [my] reading a scandalous e-mail from a then-boyfriend, someone said, ' probably want to get off of that,'" she writes. "I forgot that the computer I was using was the 'sample' screen broadcast in front of the whole audience."

Jennifer, a PR associate in California, says she was giving a presentation during a meeting when her Outlook e-mail kept appearing on screen.

"At the time, I was dating this guy that kept calling me Babydoll," she says. "He sent me an e-mail saying, 'Hi Babydoll, last night was great ;-)'"

How to avoid having this happen to you: Unless you absolutely need to go online during your dog and pony show, disconnect from the Net first, Babydoll.

The embarrassing online photo is such a staple of the Internet age that we dedicated an entire story to it earlier this fall. Even then we missed a few good ones from people who really should know better. If these guys aren't embarrassed, they should be.

Like Sergey Brin in drag, for example. As a Stanford undergrad, the Google cofounder apparently liked to explore his feminine side.

Not to be outdone, blogger Chris Pirillo is just ten fingers away from an obscenity charge in this candid outdoor shot taken somewhere in Alaska. We understand he has unusually large hands. Really.

Meanwhile, tech blogger Robert Scoble makes Pirillo look like Brad Pitt with this PR photo for his Naked Conversations book, substituting a laptop for a big pair of mitts. We think Bob needs a bigger computer--much, much bigger.

(Thanks to former Valleywagger Nick Douglas for digging these up in the first place.)

How to avoid having this happen to you: 1. For pics that escaped in your carefree college days before you sobered up and got a real job, services such as Reputation Defender will search for and destroy them for a fee. 2. When your publicist tells you "don't worry, these photos are fine," it's time to get a new publicist.

Tech Embarrassment 10: Twitterrhea

Twitter and other microblogs have inspired folks to share everything. And we mean everything. If you can say it in 140 characters or less, it's guaranteed somebody has said it on Twitter.

Here are tweets from five different Twitterati found via These people should be embarrassed, but probably aren't.

  • One of us is puking, one has diarrhea, one has tension headaches and one has a sore throat and congestion. Playdate, anyone?
  • Parasites, Parasites, Parasites. Where else can you find such words as "diarrhea," "megacolon," and "frothy vaginal discharge" together?
  • Awesome...the lady behind me just coughed phlegm all over my jacket. Gross.
  • Forgot I ate lots of fresh beets the last 2 days, almost thought I had hemorrhoids. Happy Thanksgiving!
  • Check out these beautiful bowels

(Note: That last tweet actually linked to an eBay auction for bowls.)

People, people, people. Please. Does the phrase "too much information" mean anything to you?

How to avoid having this happen to you: Besides deleting all your gross friends, using tools such as Twits Like Me or Twubble can help you find Twitter users who share your interests in (we hope) less earthy matters.

(Note: If you can contribute more embarrassing tech-related anecdotes, feel free to comment on this story.)

Contributing Editor Dan Tynan likes to embarrass his wife and children on a regular basis. The rest of the time he tends his blogs, Culture Crash

and Tynan on Tech.

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