Gmail Ads Reveal: I’m a Cross-Dressing Right-Winger Who’s About to Be Audited

Written by Sean Deveney

It’s a little weird, the way my email has taken it upon itself to figure me out. I have a Gmail account, and featured with such an account are Gmail Ads—a short line pitching a product or service, always with a link, that sits above my inbox. If you poke around Gmail’s privacy settings, you get the following explanation: “In Gmail, ads are related to the content of your messages. Our goal is to provide Gmail users with ads that are useful and relevant to their interests.”

In other words, Gmail scans messages and posts ads based on what’s inside. Imagine you write your friend an old-fashioned paper letter about how much you like your new cotton Dockers. Then you take the letter to the mailbox, and it spits out a Sears catalog at you. Gmail Ads are much the same thing.

The paranoid among us might find this a little scary, as if we’re being watched—by Google, by the government, by the Freemasons, by four out of five dentists. But it seems to me it’s just advertising, and harmless.

Still, the ads bother me, not because of the invasion of privacy—it’s what the results are that causes me to furrow my brow. Personally, I would assume that any automated reading of my messages would yield ads for sites like, or That, uh, has not been the case. I am a little disturbed by what my messages say about me. Such as:

  • I am a Depression-era flophouse drifter. I know this because Gmail thinks I would be interested in a Murphy bed: I thought Woody Guthrie was the last person to sleep in a Murphy bed.
  • I am quite the day trader. Apart from assorted retirement junk, I have bought two stocks in my life. First was Blockbuster, on the advice of a financial planner. (Ahem.) The second was Nathan’s hotdogs, on the advice of my gullet. Yeah, I like hotdogs. I bought at $12, the stock is now at $18. Despite this obviously limited interest in investment, Gmail somehow suggests, with the tagline, “5 for $5 Options & Mobile Trading.”
  • Not only do I enjoy women’s clothing, but I have a very particular and slightly disturbing fetish. I will let the Gmail Ad speak for itself: “ – Top Brand Mastectomy Fashions.”
  • I am a backer of big business. Thus, the ad featuring Gmail has clearly never read my lefty pinko blathering on The Smatter before.
  • I need a better design for my servers. This is why Gmail wants me to check out, “Free Server Room Design & Operation Courses.” Gmail is dead-on right on this one. My data server room is a mess. But whose isn’t?
  • I may have murdered someone with a calculator. That is my understanding of the kinds of cases forensic accountants solve—numbers-related homicides. If I am guilty, I am hoping that, “ – Free Forensic CPA Consultation!” isn’t on the case. Gmail says they’re the best. And no one can out run the long arm of the Assets = Liabilities + Equity formula.
  • I have trouble keeping a man. “ – 10 Dangerous Mistakes Women Make That Ruin The Perfect Relationship.” Some good advice there, ladies, but don’t confuse it with my father’s humane fishing blog, at, “”

And just for fun, I went ahead and emailed this article to myself to see what came up on the Gmail Ads banner. It was:  “About Today – How to Avoid an Audit.” Uh oh. This would be a bad time for Gmail to be right about me.

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