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Flirting Over 50? The New Rules


Not sure how to attract attention without looking like a giggly, swaggering 20-something? Here, some more age-appropriate tactics you’ll love.

By Kimberly Dawn Neumann

subtle brush of the hand, an engaging smile, an encouraging glance... by the time a person reaches the half-century mark, he or she knows all your typical “come-hither” tricks. But it’s important for midlife daters to realize that many of the tools they employed at age 20 (i.e., a hair flip with a giggle) may not be as successful at this point in their life. So what are the rules for successful mature flirting? Check out the following tips we culled from top flirting experts to help you attract the attention you crave while still being age-appropriate.

Rule #1: Always choose subtle over overt
When it comes to flirting over 50, it’s truly a case of less is more. Gone are the days of clear advances and major sexual innuendos. “There is not much to be gained by the skirt hike in this bracket,” says Susan Rabin, author of How to Attract Anyone, Anytime, Anyplace: The Smart Guide to Flirting. “Same thing goes with leaning in to flash
The tools you used at 20 (i.e., hair flip and giggle) may not be as successful at this age.
cleavage, wearing something see-through/too tight or other obvious sexual signals.” And, guys, that means you’re sexual-innuendo jokes and double entendres won’t cut it. Bottom line: You’ll seem trashy instead of appealing. A better bet? Indication. For example, Rabin suggests that in lieu of blatantly flaunting her décolleté, a woman would be smart to wear a pendant that dips down a little lower than usual. “It still draws a man’s attention to her bosom which is a turn-on for the typically visual male, but it does so without a direct ‘look at my chest’ message,” says Rabin. The point is, you can be sexy over 50 but you don’t want to look like you’re trying too hard to be sexy. And as for the guys, you can hold off on the sex jokes and references, and instead try a respectful, gentlemanly, “You look lovely tonight.” The object of your affection will get the message that you’re attracted to her without any hint of sleaziness.

Rule #2: Use formal etiquette to your advantage
At this age, good manners can actually act as a clever form of flirtation without being a blatant come-on. A man in his fifties, for instance, can put his arm around a woman, pull out her chair, or pay the bill. And a woman this age can accept these gestures or initiate one of her own by taking a man’s arm while she’s walking. Since you grew up during a more traditional age, these efforts will appear to be nothing but charmingly old-school.

Rule #3: Go for the honest approach
Lines don’t work! Seriously, if you’re over 50 and you try to entice someone with pick-up prose, the result will likely be crash-and-burn. “Using ‘Your legs must be tired because you’ve been running through my mind’ rarely works for this age group,” says Rabin, who suggests a carrying a prop (a book, for example) or making a comment on something he/she is wearing as an opener instead. Dating guru David Wygant, author of Always Talk to Strangers, agrees. “Hopefully you’re secure enough with who you are by this age to just approach someone without a cheesy opener,” says Wygant. “Try a simple ‘I couldn’t help but notice you and thought I’d say hello’ to get the conversation rolling and if things go well, ask them out for coffee.”

Rule #4: Employ “the look” and “the smile”
In honing the art of flirting, there is something to be said for a well-timed glance and grin, which is so effective it actually works at any age. Catch the eye of the person you’re trying to attract and look at them for no more than five seconds: This clearly sets up the “Hello, I see you” signal. Glance down. Wait a couple of seconds before looking up again, but this time throw in a smile when you catch your target’s gaze (you can even go
Imitation is the greatest form of flattery.
big and add a slight head tilt, too). Look away again. Repeat the process if necessary. “You can do that if someone’s nearby or if they’re across the room, but when you give those signals, if there’s reciprocal interest, he/she will usually get the hint and move closer,” says Rabin.

Rule #5: Play up innocent physical cues
Gain flirting mileage by giving off “approach me” body language. Appropriate cues include touching/caressing your hair or presenting your neck (which means elongating your posture and slightly tilting the head to one side). Also, circling a wine glass with the finger is a very sexy but subtle move. And you would do well to try a little mimicry. “Imitation is the greatest form of flattery,” says Rabin, who cites biological attraction studies to support the idea that playing copycat is a great way to flirt. “If he crosses his leg in a certain way, your cross your leg in a certain way. If she leans in a certain way, you lean in.” Before you know it, you’ll be engaged in a subconscious courtship dance without either party even being aware of the steps.

Rule #6: Be willing to talk to anyone, anywhere, anytime
Go ahead and get the chat-fest rolling. “You just simply have to have better flirting skills over 50,” says Rabin. “That includes listening, but also talking to people in line at the supermarket or while waiting for a latte.” Rabin suggests instituting the QCC policy when you see a perfect flirting opportunity. This means either asking an open-ended question like “Have you seen this movie? I’ve heard good things.” Or, throw out a comment like, “Wow, I’m not sure if that painting is the best backdrop for this restaurant. What’s your take?” And if the opportunity presents itself, add a compliment, like, “Those are terrific shoes” (though the last one can be a little tricky and must be sincere).

Rule #7: Pay attention to the personality clues you’re given
By and large, people connect and communicate via visual, auditory or kinesthetic (VAK) means, according to Rabin. And paying attention to their preference for one style of relating can be a flirting goldmine (and something the younger set probably doesn’t have patience for). For example, if someone frequently says, “I see…,” he or she is likely to be driven by the visual sense. If this person’s sentences start with, “I hear what you’re saying…” or “Listen to this…,” then they might tend toward an auditory style of relating. And those who speak in terms of, “I feel…” or “I sense that…” lean towards the touchy/feely. “If you can identify a person’s strongest sensory mechanism in the course of a conversation, you can then try to relate to them on that level,” says Rabin. That means both appealing to those senses (great eye contact for the visual person) and mirroring their communication style (saying, “I noticed that…” or “I see that….”) The likely outcome will be that the object of your attention will think you really ‘get’ them but may not be sure why. Cute trick!

Rule #8: Discover the “almost” touch
PDAs are not de rigueur for this flirting demographic. “People over 50 are usually not as demonstrative in public,” says Rabin. That said, there is power in touch. The trick is to make it about touching in a way that’s almost accidental. For women, try straightening his tie or gently picking a small piece of lint off his jacket. “It’s OK to even gently rest her head on his shoulder in a movie,” says Rabin. A man can subtly touch a woman’s arm to help guide her across the street for example. Oftentimes these little skin grazes can be even more titillating than a full-out physical offensive.

Rule #9: Remember that you can flirt for fun now!
The best part about flirting over 50 is that you can actually just flirt for the sake of flirting. “I define flirting as acting amorously without serious intent,” says Rabin. “People over 50 are usually not desperate to find a mate for the purposes of sex, marriage or children. The endgame is different, so they can just enjoy the process of being witty, playful and charming.” And it’s always nice to be considered appealing—a fabulous by-product of an innocuous flirt session. “Flirting is a great way to be reminded that you’ve still got it,” says Rabin.


Kimberly Dawn Neumann is a New York City-based freelance writer whose work has appeared in such publications at Cosmopolitan, Marie Claire, Redbook and frequently online for Happen. She has been accused of being a terrific flirt more than once.
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