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Internet dating can be daunting at any age. Here, our relationship expert offers smart advice for finding love online after 40.

Date: 2007-12-27

After her husband of 31 years died, Francine Pappadis Friedman joined In 9 months, the then 50-year-old went on 25 online dates -- all first and last dates. Recalls Friedman, author of MatchDotBomb: A Midlife Journey Through Internet Dating, "One guy met me for a drink on what turned out to be the day after his wife's funeral."

Yes, this is a groaner, but also proof that a sense of humor is a key requirement for embarking on the adventure that is online dating. Joelle Kaufman, VP of, says, "There is not as much pressure in boomer online dating. These women are not necessarily looking to marry or have kids. So they have a more casual attitude and are more flexible. For instance, many are willing to consider a man who isn't in their immediate neighborhood."

Or to consider a much younger man. Dr. Ian Kerner points out, "Younger women may be more confident with Internet tools such as Match Talk, which allows members to talk on the phone anonymously. But boomers have more world experience which gives them more confidence." Dr. Kerner, author of He Comes Next: The Thinking Woman's Guide to Pleasuring a Man, adds, "These women enjoy both pursuing and being pursued."

Plan Your Online Dating Strategy

With online dating services constantly trumpeting new gimmicks (i.e., encourages members to include references from family and friends to help demonstrate their trustworthiness), it's helpful to initiate a "battle plan" that will net maximum results.

"Most people start with giants like or JDate or Yahoo! Personals," says Erika Moore, cofounder of, which offers guidance in the art of online dating. If you're looking less for quantity than for commonality of interests, Moore suggests Googling "dating sites" or "singles" with a pertinent keyword to further refine the field. Spot- and Rover-lovers can thus sign on to, bicyclists can try, and Ivy Leaguers can meet their well-educated brethren at

Spend time crafting the perfect profile. "Stay away from cliches, negativity, and super intensity," Moore advises, adding, "My headline, which got a great response rate, was 'Bonus Points for Funny and Sane.'" And rather than littering your narrative with phrases like "love walking on the beach," Moore suggests something unique like, "'A personal paradox of sorts, I'm a quick-to-anger (Republicans) but tolerant (really cute Republicans) peacenik.'" And don't forget a great photo that is, or looks, professionally done -- full face and smiling.

Your responses to men's ads should also be thoughtful. Joelle Kaufman of suggests, "Don't send cookie cutter, long e-mails to multiple prospects. A short message that is personalized based on the person's profile is optimum."

Now for the $64,000 question: Should you fudge certain facts about yourself (i.e., lie about your age)? Kaufman says, "You can be two to three years off to get into a certain demographic on the site, but fess up quickly." The truth may not set you free, but it will always come out sooner or later. Best to make it sooner.

Protect Yourself

Unfortunately, as in the real world, cyber land has its share of bad seeds, so it is essential to exercise good sense. Stephany Alexander, author of the e-book Sex, Lies, and the Internet cautions, "Always ask for his home number to make sure he isn't married and call between 7 and 10 p.m. because that's when a committed man is with his significant other." Here's Alexander's most savvy tactic: As soon as you know his real name, run it through, a free screening service that has 20,000 men's names entered by women globally to flush out liars, cheaters, and abusers.

Just as important: Don't give him your home phone or address too soon, initially meet in a public place, and take advantage of the dating site's "anonymous" e-mail feature until you're 100 percent certain he's trustworthy.

Of course most members aren't con artists. But odds are there'll be one or two you wouldn't want to be trapped in an elevator with, much less across a romantically set dinner table. So make the initial meet quick and cheap. Starbucks was invented for online dating.

Use this short "look see" to detect red flags such as your companion's tendency to check out every female within range. Even if he has a scarlet L for LOSER stamped on his forehead, Francine Pappadis Friedman, she of 25 online first and last dates fame, says, "Be nice. There were a few guys who made me want to lock myself in the ladies' room, but it's important to remember each of them is coming to the table with his hopes, dreams, expectations, and baggage, just as you are."

Not interested? As you part, say a polite, "It was nice meeting you." The message -- don't 'e' me; I won't 'e' you -- should be received. If it's not, let him down gently: "I enjoyed your company but don't feel we're a match." If he still won't vanish into the cyber-mist, check out the site's technology allowing you to block someone's e-mail.

If he's the one who boneheadedly rejects your fabulous self, dive right back into the Internet pool. But don't rely on online dating alone as your source of potential romantic partners. Ideally, it is one prong of your man-meeting approach, not the entire strategy.

However, utilized wisely, online dating can be extremely effective. "Many people I know met the loves of their lives this way," says Friedman. "I succumbed to 'chronic meeting syndrome' -- too many dates in too short a time and burnt out." Is she considering a second run? "Very likely I was just unlucky."

Originally published on, June 2007


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