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A Friend Stopped By | 07/22/2008 11:00 am

The Over-40 Flirt: A Definitive Guide

By Dr. Judith Sills
© Liza Donnelly

Relationship expert Judith Sills’s surprisingly robust rituals for a romantic response

Babies flirt because it comes easily to them and septuagenarians flirt if they still have the juice. In between, the rest of us flirt when we find our footing, though the ground gets momentarily shaky after big birthdays. But it doesn’t have to. You can keep your flirt all your life, if you polish up your act over time.

Click here for an illustrated guide to Flirting After 40!

At any age, flirtation is simply the expression (mostly but not entirely nonverbal) of interest and (mostly but not entirely sexual) appreciation. And, of course, flirting is the desire to attract that very same interest and appreciation to yourself. The main difference between flirting at 15 and flirting at 50 is in what you are using as bait. Fifteen is flirting with a seductive innocence and enthusiasm; 50 is flirting with erotic self-confidence and experience. If you don’t confuse the two, you’ll enjoy yourself. These guidelines may help:

1. Are you in town or on the road?

Fifteen is flirting with innocence; fifty is flirting with erotic self-confidence and experience. If you don’t confuse the two, you’ll enjoy yourself.

Flirting in front of a hometown audience — at your club or your girlfriend’s dinner party — requires restraint because single women are scrutinized by their closest friends for any signs of poaching. Under these conditions, avoid any personal comments. (“That tie and shirt are fabulous. Did you pick that out yourself?” Smile. Eye contact.) Instead, gift wrap all connecting remarks in intellectual banter. (“I agree. It was his most intriguing column.” Smile. Eye contact.) Outside your social circle you can do anything that feels like fun to you, even mouthing the words “I love you” to a total stranger, just to see what would happen. Because, ultimately, wherever you are, flirting is at least partly just for the fun of it.

2. What’s your desired outcome?

Are you seeking a simple lift of the spirits? (Make bold eye contact and smile. He’ll smile back and you’ll feel good.) Are you thinking perhaps a sexual fling might be in order? (Approach and start a slightly personal conversation. Touch him casually, early on. If he isn’t interested, move on. Going much further is unattractive stalking.) Are you hoping for something more traditional, like an introduction or a date? (Separate from the group and put yourself in his physical proximity, turning slightly towards him. If necessary, make one connecting comment. “How’s that wine?” He has to take it from there.)

The advantage you have over 40 is that you can be conscious of your agenda.

3. The wardrobe, the shoe and the cleavage question.

Of course you will be yourself, but it helps to be the self that is signaling she is a sexually alive woman.

That woman is only wearing running shoes if she is flirting during a marathon start; she is only wearing a flax sack if she is flirting during apple picking; she is only showing major cleavage if hers has magically maintained — or at least been surgically restored to — some pre-40 state of desirability. Otherwise, you will be wearing some tolerable form of girl shoe (because it puts you in the flirting frame of mind), clothing that reveals your body contour (because that puts men in a flirting mood) and you will wrap your sexual skin in whatever enhances it most.

4. Don’t be afraid of the Bold Approach.

Send him a drink. Hand over a chocolate kiss when you see an attractive prospect. Drop your business card in his lap. (Be prepared for him to confuse you with a hooker. This is not necessarily all bad.) Send him a text message that says you are ovulating. Call and ask his advice (on your car troubles, your travel plans, your wine choice – think of something). Throw a party and tell him it won’t be any fun if he isn’t there.

5. Use technology for practice.

Send a person of interest an e-mail joke, or an article you thought he’d like. Send everyone electronic valentines. Take the risk.

55 Reader Comments (so far…) Sign In or Register to comment

Linda Clark
Signs of Poaching” ………….. I can say that I’ve never heard that term before. I guess that also means that I’ve never flirted with my hubby’s friends ……. oofta, and thank goodness for that one!
By Linda Clark on 07/22/2008 11:02 am
Tee Zee
What’s wrong with just a simple lift of the spirits (Make bold eye contact and smile. He’ll smile back and you’ll feel good.) - I try to smile at both men and women more these days…there’s way too much negative in the world. I don’t want it to lead to anything… except maybe great conversation. Don’t we all wish we had more great conversation? I only forward email with a positive message…there’s way too much junk in our lives.
By Tee Zee on 07/22/2008 11:08 am
Marjorie C.
Flirting’s good at all ages, but safest and most appreciated as the years pile on. Safest in the sense that you don’t have to be concerned about misleading someone.
By Marjorie C. on 07/22/2008 11:31 am
Lady Gator
Send him a text message that you are ovulating”. Now that would be different!!! LOL
By Lady Gator on 07/22/2008 11:55 am
Dr. Mark Klein
When I was young, to get sex in my world most guys had to be at least be engaged. Been the best of times for men since “the zipless fuck” became the gold standard for female sexuality. Re suggestion #5 I’ve got a joke. A guy sees an old buddy who once had a huge fortune scavenging for food at a dumspter. He asks how he lost his fortune. The man replied he lost 2/3 in the uninsured losses of his private jet and yacht and remainder in a divorce. Went on to say he learned from his experience if something flies, floats or f***s, rent!
By Dr. Mark Klein on 07/22/2008 11:57 am
kermie b
Mark, that is in bad taste on a woman’s website. Not funny.
By kermie b on 07/22/2008 2:07 pm
kermie b
By rent I am guessing you mean prostitutes? That was last week’s discussion.
By kermie b on 07/22/2008 2:52 pm
Frank Peterson
Mark i’ve told you before get your ass outta the paleolithic, will you—tasteless just doesn’t described your writing or your behaviour. Grow up.
By Frank Peterson on 07/22/2008 2:26 pm
James the Game
Agreed, Franko. I would be embarrassed to write or speak around women the way some men do. Being a so-called “nice guy”, I may finish last, but at least I cross the finish line with my dignity intact.
By James the Game on 07/22/2008 4:31 pm
Frank Peterson
Jame s exactly.
By Frank Peterson on 07/22/2008 5:08 pm
Star Lawrence
Oh, Markie Mark—how did she ever let you go?
By Star Lawrence on 07/22/2008 2:39 pm
Frank Peterson
Probably with rabid guard dogs and a whip.
By Frank Peterson on 07/22/2008 2:49 pm
Linda Clark
Star and Frank ………I’m ROFLMAO! Thanks, I needed a good laugh!
By Linda Clark on 07/22/2008 3:09 pm
B. Nyce
Dr.” Klein, Please refrain from the use of profanity on this website. Thank you.
By B. Nyce on 07/22/2008 7:41 pm
No Way-No How -No McCain
Duchess is that you? Or has ‘B. Nyce’ made off with your tiara?
By No Way-No How -No McCain on 07/22/2008 10:59 pm