THERE are many ways to console someone when a multimillion-dollar business deal falls through. Firing off a “tough break” e-mail message punctuated by a frown-face emoticon is not one of them. Emoticons, the smiling, winking and frowning faces that inhabit the computer keyboard, have not only hung around long past their youth faddishness of the 1990s, but they have grown up. Twenty-five years after they were invented as a form of computer-geek shorthand, emoticons — an open-source form of pop art that has evolved into a quasi-accepted form of punctuation — are now ubiquitous. “In a perfect world, we would have time to compose e-mails that made it clear through our language that we are being cheerful and friendly, but we’re doing these things hundreds of times a day under pressure,” said Will Schwalbe, an author of Send: The Essential Guide to Email for Office and Home, written with David Shipley, the deputy editorial page editor at The New York Times. Schwalbe said he has seen a proliferation of emoticon use by adults in delicate and significant communications. “It’s really in the last couple of years that the emoticon has come of age.” In a survey of 40,000 users of the Yahoo Messenger instant-message programme, 52 per cent of the respondents were older than 30, and among those, 55 per cent said they use emoticons every day. Nearly 40 per cent of respondents said they first discovered emoticons within the last five years. Christopher P. Michel, the founder and chairman of Military.com, a military and veteran affairs Web site, said that usage of emoticons has grown “hyper-pervasive” in his communiques even with admirals at the Pentagon, where they provide a certain cover for high-ranking leaders to comment on sensitive matters. “A wink says quite a lot,” said Mr. Michel, a former lieutenant commander in the Navy. After 25 years of use, emoticons have started to jump off the page and into our spoken language. Even grown men on Wall Street, for example, will weave the term “QQ” (referring to an emoticon that symbolizes two eyes crying) into conversation as a sarcastic way of saying “boo hoo.” Though we think of emoticons, or smileys, as an Internet-era phenomenon, their earliest ancestors were created on typewriters. In 1912, the writer Ambrose Bierce proposed a new punctuation device called a “snigger point,” a smiling face represented by __/!, to connote jocularity. The first commonly acknowledged use of the contemporary emoticon was in 1982. Scott Fahlman, a research professor of computer science at Carnegie Mellon University in Pittsburgh, was linked to an electronic university bulletin board where computer enthusiasts posted opinions on matters as divisive as abortion and mundane as campus parking. In one thread, a wisecrack about campus elevators was misinterpreted by some as a safety warning, so Dr. Fahlman suggested using :-) as a way to indicate jokes and :-( for remarks to be taken seriously (the latter quickly morphed into a signifier of displeasure). To Dr. Fahlman’s surprise, his “joke markers” spread quickly on the board. Within a month, he heard, some peers out in Stanford had picked them up, and soon after, techies at Xerox were circulating a list of strikingly sophisticated new emoticons. He never received a trademark for his invention, and never made a dime from it.-ALEX WILLIAMS ( New York Times)