As his thumbs danced over his cellphone's keypad, Toronto transit chairman and mayoral candidate Adam Giambrone likely assumed only one person would read the following message: "I like you because you're smart and interesting. You're also good-looking naked."
The flirtatious text was allegedly sent to Kristen Lucas, now a 20-year-old university student, who claims she had a secret affair with the city councillor.
This week, Ms. Lucas released that text message - and several other incriminating ones - to the media, much to the embarrassment of Mr. Giambrone, 32, who has a live-in girlfriend.
If the allegations are true, the politician joins the ranks of Tiger Woods, South Carolina Governor Mark Sanford and a host of others who are no doubt face-palming over their decisions to send racy messages digitally.
Tech experts have long discouraged sending risqué photos and e-mails via corporate accounts, since managers can easily intercept them. But now it seems the greater threats are the recipients of these naughty communiqués.
Hal Niedzviecki, Toronto author of The Peep Diaries, explains that it's become so easy to fire off messages from electronic devices that most people don't realize they're adding their thoughts to a permanent record.
As cellphone and e-mail inbox storage increases, he says, saving digital exchanges has become the norm. And when things turn sour in a relationship, those intimate messages can become powerful ammunition against an ex-lover. (Mr. Giambrone has admitted to having an "inappropriate relationship" with Ms. Lucas, but denies it was sexual in nature.)
"[With the devices]the default is to save, whereas the way the human brain works and the way human relationships work is delete," Mr. Niedzviecki says. "It's not a celebrity problem, it's not a politician problem - it's an ease thing. It's a case where technology is changing morality without us even considering it."
He points to when White House employee Linda Tripp surreptitiously recorded phone conversations between former U.S. president Bill Clinton and White House intern Monica Lewinsky in the 1990s. He says her behaviour was seen as "unethical in our greater society."
"Whereas now, if you were to forward someone's theoretically private messages to you that come in a text message or Facebook or e-mail, you don't get in trouble," he says.
When Los Altos, Calif. writer David Mott was working in the tech industry in the mid-nineties, he remembers rumours of an affair between Oracle co-founder Larry Ellison and his secretary that came with e-mail evidence.
The e-mail turned out to be fabricated, and the secretary was found guilty of perjury, but it still made Mr. Mott leery of using e-mail to discuss private matters.
"I definitely remember that happening and thinking I definitely don't want any e-mail trail from a relationship," he says.
The 46-year-old divorced father of two says he also refrains from sending flirtatious Facebook messages to the women he dates for the same reason. But he does have one digital weakness: "I text like crazy," he says.
Mr. Mott admits he's sent plenty of sexual text messages to girlfriends, but says that because he's always been in open, honest relationships he's not afraid of any of those saved messages being used against him.
"I can see where it would bite celebrities and politicians in the butt, but for me I honestly don't worry about it," he says.
Mr. Niedzviecki theorizes that it's a combination of the ease of forwarding information and hunger for the spotlight that induces people to forward private messages to a wider audience.
"It's sad because we have this amazing way for people to communicate and connect with each other ... [and]it's proving to be very dangerous and divisive in our society to use it the way we use it ... without self-censorship," he says.
Jeffrey Kishner, New York-based editor of TechCoquette, a dating advice and etiquette blog for the tech-savvy, says revenge is the main motivator in most cases of e-mail and text-message forwarding, but sometimes the scorned just want to set the record straight.
"Some people want to demonstrate that they were not in the wrong in the relationship when it ended," he says. "If they have some kind of record that says, 'Look, he was the jerk and I have proof,' it might make them look better and clean their slate."
While he says there are no black-and-white rules for what should or should not be discussed through e-mails or texts, he believes senders should keep one thing in mind: "Anything that's going to leave a digital imprint, you should really think about 'Is this something that I'm comfortable with ... them sharing with the world?' "
While Mr. Mott has unwittingly developed a strong arsenal of messages he could use against some of his exes, he insists he'd never pull the trigger.
"I've had some women send me risqué photos in e-mails, and I've kept those. But not because I intend to use them against her, but because they're good photos," he chuckles. "They bring back good memories."