When Gmail ads get too intimate

It's marvelous how wickedly clever engineers are at finding ways of placing ads next to just about everything you do online.

Cookies are stealthily slipped into your laptop like roofies into a margarita. Suddenly, you are reading an English newspaper when up pops a helpful advertisement offering you a rather model-featured companion ready to curl up with you in your ZIP code.

It seems, however, that some Gmail users are becoming increasingly disconcerted by the ads that Google is placing around their more personal communications. I received, for example, an e-mail from a reader called Keegan. His story is a simple one.

He was reading an e-mail from Apple regarding iPods and the perfect Valentine's gift. That's when he noticed the related information line at the top of the screen. It had nothing to do with Apple or iPods. Instead it referenced a much more intimate type of Valentine's gift.

Who could not be amused by such creative thinking from a mere algorithm? It is such beautiful and lateral thinking. Um, iPod. Um, Valentine. Yes, vibrator!

As Keegan ruefully told me: "An iPod Touch may be a personal pleasure device, but the apps have not yet reached the same level of satisfaction that [another device] may provide."

Keegan's case does not appear to be isolated or necessarily new. Gmail user Sucan complained that when an e-mail about a sick cat arrived, an ad about "estate planning and funeral planning" appeared.

It is one thing, perhaps, to see mildly annoying ads next to searches. But the very nature of e-mail demands a certain privacy, one that seems to interest Google not in the least bit. Indeed, if you read Google Help, you begin to realize that the company really does seem to believe in the "goodness" of its ads. However, this "goodness" may well have something to do with the very good relationship between engineering and money.

Last month, Google made changes to its Gmail ad sprinkling. Google Help helpfully indicates that these targeted ads are now even more, well, good: "Until now, the ads you've seen next to a message were picked based on the content of that message only. For example, if you're looking at a confirmation e-mail from a hotel in Chicago, you might see ads about flights, restaurants or other things relevant to your trip to Chicago."

But hark at this excitement: "Sometimes, the ads related to a particular message aren't good enough." That cannot be possible. Surely that must be system error. Not GOOD enough?

Google has a solution that improves on its astonishing advertising excellence: "Rather than show less relevant ads, Gmail can now instantaneously serve ads based on another recent message on the same page of your in-box, helping make the ads more relevant to you."

Google's example of this improvement is blissfully simple: "If your friend sends you a message to say happy birthday, but there aren't any good ads to show related to birthdays, you might see ads related to another message in your in-box instead -- like flights to Chicago."

You mean they wouldn't be able to find an ad that related to "happy" instead? I am mesmerized, though, by the phrase "aren't any good ads." What makes an ad "good"? What, indeed, makes a vibrator ad good with respect to an e-mail about iPods and Valentine's Day?

I tried an experiment--out of the goodness of my heart. I sent three e-mails, one after another, from my usual e-mail account (not Gmail) to a Gmail account that doesn't carry my own name. I allowed time for each to be received and read.

The first read: "I don't know what to do with my iPod for Valentines. Should I listen to it? Should I give it away? Or should I buy my Valentine something better? What do you think?"

Having received the e-mail, the Gmail account offered the fine suggestion of "Frye's shoes at Zappos."

I sent a second e-mail in the same way. This one, following the Google example of Chicago and birthdays, read: "I have a birthday and I am going to Chicago. What do you suggest I do? And should I do it with Laura?"

Google offered me the exact same ad about Frye's shoes (which I have never worn or bought) at Zappos.

However, I then sent a third e-mail: "I don't know whether I should have sex with my girlfriend on Valentines. Do you think it's a good idea? Or should I just get her something at Zappos?" This was sent within a minute or two of the previous two. Surely I would get the same Zappos ad again.

Surely not. Please see the screenshot. The Google machines suddenly ignored my clear mention of Zappos and tried to inspire me with a couples massage in San Jose, which is more than 50 miles from where I live.

We allow ourselves to participate in some strange mind-games if we live by the logic (and the goodness) of Google.