When Dinah Larson was single, she and a friend used to read e-mails from guys and decide if they were potential dates based on their e-mailing ability.

"If he wrote like he talked, and was funny? He WON," explains Larson, a 30-year-old marketing director who lives in Los Angeles. "Judgmental, yes, but it was a solid correlation every single time. Of course, this all predated the whole IM-speak phenomenon, but I can’t imagine either of us even considering a boy who was too lazy to spell out entire words."

Larson and her future husband, who met at a conference but lived in different cities, fell in love over the Internet by exchanging five or six e-mails a day.

"(He) used to write me AMAZING e-mails. Now, of course, they’re more like, ‘If you’re stopping by the store on the way home, we need trash sacks.’ "

These days, e-mail is an essential flirtation tool for a whole generation of Americans. So are instant messaging, text messaging and message-board posts; but with those, people give you a little more leeway. Form there isn’t as important as content; there’s a reason to use as few letters as possible and no punctuation. And what you write disappears in the blink of an eye.

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E-mail is different; it sticks around to be read and reread, even printed out.

Did she use too many emoticons? Did he really have to write ROFLMAO to show he was laughing? E-mail falls somewhere between a phone call and a letter, but it has rules and pitfalls all its own.

"Instant messaging is better because the interaction is in real time," says Phil Maggio, who writes about Internet dating under the nom de plume Sebastian Chance and found his wife, a native of China, in an Internet chat room. "People reread their e-mails and use words they wouldn’t use normally."

"If someone doesn’t spell ‘you’ out in an e-mail," says Alexandra Robbins, author of "Conquering Your Quarterlife Crisis," "I assume the writer is in middle school. E-mail is today’s form of a postal letter."

It’s a scary thought. How good you are at cyberspace communication could determine your future — at least as far as your love life is concerned.

Great e-mailing can’t be taught. It’s a gift. Kristen Tubman, a 25-year-old who lives in Mount Washington, Md., and travels a lot, still remembers the first e-mail she got from a friend in Honduras after he had put her on a plane back to the United States. "The e-mail was all about the many buses he had to take to get back home." She loved it, which says something about his writing ability.

There are potential hazards with e-mail as a way to get to know someone before you even strike the first key. Take a look at your user name, suggests Lesley Carlin McElhattan, an etiquette maven for the new millennium. (See the Web site etiquettegrrrls.com.) "It reflects who you want to be. If someone’s (address) is starwarsforever@aol.com, be wary."

Still, for anyone who’s a little shy, e-mail is safer than picking up the phone and making that first call. "It’s easier than fumbling through a voicemail message they can’t erase," points out Kermit Blaney, a 29-year-old who lives in Canton, Md. "The initial contact of e-mail alleviates all that."

If nothing else, it can be proofread and reworked when it doesn’t sound quite right.

"Just as people used to fret about the rules on when to call someone back," says Robbins, "now they agonize for hours over a four line e-mail. Should I punctuate with a winky face? Will he think it’s a cute winky face? A sexy winky face?"

How you present yourself in instant messaging and e-mail has become even more important because so many people are using dating sites and online communities like MySpace.com these days. Sharon Frost, 26, whose photos on MySpace (myspace.com/khoney) draw plenty of admirers, doesn’t ask for much from the initial cyberspace message.

"If you just write to me and say, ‘You’re hot,’ I don’t bother to answer. If you say, ‘Your elbows are pretty’ as a way to break the ice, that’s different." Frost, who lives in Ellicott City, Md., isn’t happy with "love your tattoos" either.

Lori Burton, 26, responded to a first contact on a dating site by checking the guy’s profile, which seemed interesting, and then sending a two-paragraph, friendly, chatty e-mail with questions. She got this response:

"It been pretty uneventful as of late. Nothing good or bad happening. Well Hope you had a good weekend or our enjoying one. So what is it you do for work. Are your from maryland."

"All spelling and grammar errors aside, even if you struggle with typing, just simply say, ‘Hey, I can’t type so well. Can I give you a call?’," the Parkville, Md., resident says. "But this e-mail is an entirely unacceptable and inappropriate response. I just don’t have time to get to know someone two sentences at a time. Sorry."

It’s a fine line. How short is too short and how long is too long? Strike a balance between being specific but not going overboard, says Kathleen Roldan at the dating site Match.com. "People are put off by very long e-mails. A rule of thumb is you should see it in one screen. Anything you have to scroll down is too long."

Maybe the biggest problem with e-mail and instant messaging is that cyberspace communication feels almost like talking, but you lose tone and nuance. Sarcasm can come across as just plain mean. That’s the main reason emoticons have become so popular (although a "just kidding" works just as well as a smiley face if you’re not the smiley face type).

An e-mail is a first impression, like a first date face-to-face.

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"Usually if people seem too eager, those I don’t answer," says Amy Jarboe, a 30-year-old Towson, Md., resident who’s just getting into Internet dating.

Match.com advises members not to stay in the e-mail stage for long. "Just because it’s online dating doesn’t mean you’re dating online," Roldan says.

But until you get to that point, all the date protocols translate into cyberspace, warns author Robbins. The guy who doesn’t read his e-mail carefully — that suggests something about what he’d be like as a boyfriend. As does the woman who talks too much about herself.

Roldan at Match.com agrees. "So many of the dating rules apply. Don’t e-mail every hour. Don’t bombard the person with thoughts every five minutes."

Getting back to people quickly is important if it’s a potential dating situation, says Etiquette Grrrl McElhattan. "It’s the same as not returning a call if you don’t."

If the e-mails are turning personal, get them off your corporate address as soon as possible, she says. "If it was a love letter, you wouldn’t share it with your boss."

In general, McElhattan advises, keep things light if you’re getting to know someone by e-mail. And steer clear of religious and political content. "It can look nosy or proselytizing," she says. "Do it in person."