The Best Book on Dating More After 40

Jerusha Stewart, "The Last Single Girl In The World," and author of "The Single Girl's Manifesta," kisses and tells all about how to date more after 40.





At over 40 singles events you often hear men and women complaining about how hard it is to be single at their age. Some are divorced, a few have never been married but they all seem to have lost their belief in serendipitous sex or lasting love. Here is why dating gets better with age…

You’re older and wiser.

You know what you want this time out of a relationship.

You are not desperate.

You are dating because you want to, not because you have to be part of a couple. You are happy with the life you have made for yourself. You have achieved much. Realized your dreams and know you can enjoy life on your own.

They are plenty of new ways to meet singles your age.

Technology among other thing has revolutionized dating. More matchmakers and organized events are focused on uniting boomer babes. Many more resources are available for meeting the opposite sex than when you were younger.

You are healthier & living longer.

There is still time to enjoy life with the man or woman of your dreams.

Life gives you second chances.

Look at the later in life romances of Prince Charles and Camilla or Donna Hanover, the former wife of the mayor of New York who married a former college classmate.

You are much more interesting than you were in your twenties.

All the awkwardness is gone. You have grace and conversation peppered with life experiences. Time has made you irresistible!

You can now really and truly appreciate the love of another person. You don’t sweat the small stuff, and you have learned what really is petty and insignificant and not worth fighting about in a relationship.

The rules have changed.

You practice no excuses dating and fearless flirting. You no longer feel obligated to date jerks or to wait for an invitation from someone you are really interested in seeing again.

Falling in love is different after 40.

It can be deeper, richer after the reflection on life’s past romances. And the rewards can be as great as someone to spend the rest of your lifetime with in great harmony.

DATE MORE CHALLENGE: What is stopping you from looking for love or lust right now? Is love really the answer or do you have another question?

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It is not what you say but how you say it. Very true piece of wisdom when it comes to dating older ladies and gents. Singles over 40 and well past 50 can be a tough audience. They are bound to feel they have heard it all before. Whether it is paying a compliment or getting to know the other person on a date, here are some helpful tips to make you a smoother talker.

The Name Game.

Introduce yourself. Sounds simple enough. Often when we meet someone for the first time at a dating event we may feel a bit awkward or nervous and forget this important of bit of information. Don’t rely on the nametag to communicate who you are at this crucial juncture. A simple, “Hi, my name is___” or “You look beautiful tonight. By the way, my name is_____,” is the best icebreaker ever.

Make yourself even more memorable my remembering their name and using it whenever you see them throughout the evening. If you have trouble remembering names, repeat it when you are first introduced, “Hi Jenny, nice to meet you.” This will make sure you have it right and are pronouncing it correctly. Studies show that people enjoy hearing their names spoken. You are flattered that you remembered.

Don’t break the connection.

Encourage an open-to-chat atmosphere by becoming comfortable using a few simple conversational tools. Mimic the posture of the other person. Copying physical behavior puts the other person more at ease and communicates likability. Make eye contact. This is not the time to show off your latest shades or make a study of your shoes. Remember most people believe that the eyes are the windows into the soul. You close that window; they will be less likely to open the door to another date with you.

Eliminate the word “but” from your dating vocabulary.

It translates in our brains as the word “no.” You want the other person to be thinking “yes” about spending time with you. In most instances the word “and” is good a substitute and tends to foster more positive feelings.

Getting to know him/her.

If you are interested in the person, you probably have a thousand questions, which can feel as uncomfortable as a job interview or an interrogation to the other person. Don’t ask yes or no questions. Instead of saying, “Do you like old movies?” Ask an open-ended question like, “What types of old movies do you like to watch?” This invites the person to express a point of view.

Making it personal.

Afraid a question may be too personal, begin it with “I hope you don’t mind me asking…” This gives the other person the opportunity to decline and graciously change the subject. It is also easier to ask personal questions by prefacing them with a few simple phrases. Say, “Just out of curiosity, what attracted you to my profile?”

Did you know?

Instead of sounding like a know-it-all, express your interest by saying, “I don’t know how much you know about (pick a subject) …I’m attracted to it because…” This introduction to the subject matter invites them to join in at their own level of interest and shows you’re interested in their thoughts.

Getting to “like.”

For a conversation starter which subconsciously links the two of you, begin your statement with the words, “If you, like me, enjoy…” You have also included a subliminal trigger as well which plants the idea that “you like me.”

Be genuine. Be passionate. Be real.

If you had a good time – don’t be shy about letting the other person know: “I really enjoyed meeting you and I’d like to see you again.” If not simply say, “I don’t think we have enough in common to pursue this any further. Thanks for meeting me.” This is enough to let the other person know how you feel. Don’t go into detail. Be polite and end the evening.

DATE MORE CHALLENGE: Are there some people you really enjoy talking to more than others? Compare their conversational styles with your own.

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You are all victims of a grand fashion conspiracy: grown women are being made to believe they don’t have a clue as to how to dress themselves! How else can you explain the proliferation and popularity of makeover and style counsel television shows? You have gone from your mothers shrieking, “You’re not leaving the house in that!” to unsuspecting women being fashion “punk’d” by style gurus on cable television shows. All this unsolicited, yet 24/7 advice has you second-guessing your wardrobes and your ability to get dressed for that all-important event: The First Date. Check off these seven common sense rules for over 40 date dressing success.

Don’t wear black.

It is already dark enough in that club, restaurant or movie theater you will probably wind up in. Your mission is to stand out, not blend in with your surroundings. Besides, an unofficial poll of single guys found that they find the color totally desperate – and boring.

Don’t wear your closet.

This is not the time to layer your favorite shirt underneath that gorgeous sweater you just could not resist from the mall and cover them with ropes of chains and pearls. With that much eye candy, your guy may have trouble figuring out where to focus. You are trying to win is attention not “Project Runway.”

Skip the Fashion Forward Fashions.

Don’t show up in anything that makes you look like you have been wrapped, twisted or tied up in knots. This only leads to wrong-way thinking on his part, such as, “How did she get into that get-up … and how am I supposed to get her out of it?” Besides, throwing out hints of one’s personal bondage fantasies constitutes way too much information on the first date.

Focus on looking great above the waist.

Chances are, most of the evening you will be sitting down. Spend your resources presenting a pretty picture that he can see. Give him something to talk about: a blouse in a great color, a well-made top that shows off your shoulders, or jeweled earrings that catch the light. He may not necessarily know fashion, but most people know what they like in colors and shapes. That color on you, the shape of that shirt on your curves.

Embrace color.

You don’t have to dress in a Technicolor splash, but a little color around your face will bring out your eyes and your smile. The right shade will make you look rosy when you feel ill from the food or something he says. Men love red – from fire engine to cherry tomato to raspberry rich red. Sensuality and sophistication demand that you choose the appropriate shade for your skin tone. Adopt a signature shade. Use the rich hue to get up close and personal.

Fit and flatter.

Don’t worry about size. Focus on fit. When the dress is on you, it should fit you and not your imaginary size. Be real: we all have bags we don’t want to carry and rolls we wish would roll away. The important thing is to master the art of disguise and invest in your assets. When that dress is lying on the floor, I guarantee you he will not be looking at the size on the tag.

Lastly, a date is not the same as the big reveal.

Flaunt your best features, but not all of them at once. A plunging neckline does not need to compete with a thigh high skirt. Less is more. The less you show now, the more you will have for later.

DATE MORE CHALLENGE: Routinely stumped by your closet when getting dressed; inventory your closet. Note which pair of jeans makes your butt look high and tight; jot down which slinky dress makes you feel like a million bucks. Put together a dream collection of knock ’em dead date styles.

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