Man looking at laptop with a beer in his hand

For a company that’s dominated the Internet by doing one simple thing well, Google has also managed to build a thriving side business in bells and whistles: its features offer everything from the ability to search inside books and videos to the ability to watch a kid fall off a bike from the privacy of your own home. So when I heard that Google had unveiled a new feature called Mail Goggles that is designed to stop you from sending embarrassing e-mails while drunk by requiring you to do math problems, my first thought was, That’s the most ridiculous thing I’ve ever heard. My second thought was, I want to try it.

One of Gmail’s optional features — along with more sensible applications like keyboard shortcuts, an e-mail signature or a profile picture — Mail Goggles operates on the theory that if you’re sober enough to complete a series of simple arithmetic problems, you’re sober enough to decide if you really want to e-mail your ex-boyfriend and tell him you still love him. With Mail Goggles enabled, Gmail will send your e-mails only after you have completed five arithmetic problems within 60 seconds. By default, the feature activates during weekend nights between 10 p.m. and 4 a.m., although the settings allow you to change the date and time. If you’re more of a Tuesday afternoon drunk, Mail Goggles will be there for you. Of course, at that point, you might have bigger problems to worry about. (See pictures of Denver, Beer Country.)

I decided to test Mail Goggles in the most systematic way possible. I surrendered my Saturday night to research, experimentation and the scientific method.

Mail Goggles will keep me from sending e-mails that I might otherwise regret.

2 bottles of wine
1 laptop
My college friend Laura, who once helped me climb up a concrete pedestal in order to dress a Civil War statue in a Hawaiian T shirt.

The test:
10:03 p.m. Mail Goggles is activated. I send a control e-mail to test my sober math skills. I subtract 12 from 22, and wonder if I’ll ever be too incapacitated to come up with the number 10. “You know you can change the difficulty level,” says Laura. We pour ourselves some wine, change the difficulty to Level 3 and start watching a movie. (See the 100 best movies of all time.)

10:25 p.m. I’ve had one glass of wine. I reply to a friend’s e-mail about her recent bad date. Mail Goggles doesn’t work — no math questions appear and the e-mail is sent. “Maybe you have to sign out and sign back in,” suggests Laura. That works. If this is a necessary step, though, it’s a huge flaw in the Mail Goggles system; nobody signs out of Gmail after every use.

10:45 p.m. Two glasses of wine. I e-mail another friend and tell him that his eyebrows are too big and he looks like one of the Jonas Brothers. I have this thought every time I see him, but I usually keep it to myself. The e-mail goes through. My friend will now ignore my phone calls for the next few days. I decide to change Mail Goggles’ setting to maximum difficulty, Level 5.

11:10 p.m. Three glasses of wine. The problem 420+152 is not hard enough to keep me from e-mailing an acquaintance to tell her that I don’t understand her religion and her clothes are out of date.

11:35 p.m. Three and a half glasses. I feel great. It takes me two tries because I mistype my answers, but I successfully e-mail Laura to tell her that I want more wine. “But I’m sitting right here,” says Laura. She politely opens the second bottle.

12:17 a.m. Four glasses. To my unemployed friend with a master’s degree: “Why don’t you move out of your parents’ house and get a real job?”

12:43 a.m. E-mail a co-worker and complain about the economic depression.

1:09 a.m. Mail Goggles makes me answer “8 x 2” twice. I use this opportunity to tell my cousin that her feet smell.

1:37 a.m. I drink some more wine and try to tell a friend that his hipster arm tattoo is going to look ridiculous when he gets older, but I can’t type the words correctly and I get stumped on 517-139. I keep forgetting to carry the numbers. “Water and bed for you,” says Mail Goggles, but then it lets me try again. And again. My insult succeeds on the third try.

1:52 a.m. You know what? I should e-mail my ex-boyfriend, even though we’re not on speaking terms. Mail Goggles makes me divide 42 by 7 but otherwise has no problem with my incredibly bad decision. Maybe the program would work better if it filtered certain phrases like “What’s your deal?” or “jerkface.”

2:32 a.m. I write one last e-mail, apologizing for the previous e-mail, but I’m too tired to do the math.

2:47 a.m. I fall asleep on the couch and wake up half an hour later, thirsty and confused. Laura has apparently gone home.

10:15 a.m. I have three responses asking what my problem is.

Mail Goggles’ math questions are too easy to deter any but the sloppiest of drunks. However, my last e-mail remained unsent. If you have to do math at 2:30 in the morning, you’re more likely to stop sending e-mails because you give up, not because you actually get the answers wrong. As a purely dissuasive tool, then, Mail Goggles works as advertised. Of course, there’s still the text message, the Facebook message and the good old-fashioned drunken phone call. There are plenty of ways to humiliate yourself if you try. And for those determined to reveal their true feelings via e-mail, the company that brought you Mail Goggles helpfully provides a way around it as well: the Google calculator.


(Editor’s Note: This is a reprint of an old TIME Business & Money article that is still worth a read as a good example of exploratory testing. The original, with links, is available at,8599,1849897,00.html?imw=Y#?iid=perma_share

For a review by a software testing guru, see


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