Tag: older women dating younger men

  • “I’m afraid to date”

    The attractive mature woman approached me after my talk on dating after 40. She said she admired my courage to take on dating so enthusiastically, but she was afraid to start dating.

    I asked what her fear was.

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  • Are you on the same train to boo-ville?

    What determines if you are an item? Is it agreement about exclusivity? Is it the fact that neither of you is interested in seeing others?

    You may think that his regular calls, texts and weekly dates makes him your beau. He may think that you are just one of the women he is seeing, even if at the moment he’s not seeing anyone else. You may feel that by your sleeping together regularly, you are going together. He may feel that you are a woman he’s hanging out with.

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  • Feeling like a mail-order bride

    You’ve struck up a nice communication with a man who seems to fit many of your criteria. He’s smart, educated, polite, funny, well traveled, successful and clearly interested in you and your life. His age, height, and economics are in the right range for you. You’ve talked on the phone several times and you’ve had email, IM or text conversations every day for a week.

    You usually like to meet a man in person within a week or 10 days — before spending too much time flirting virtually. You know it pretty much all hinges on how you feel about each other face-to-face. It can enhance your growing fondness toward each other, or it can fall flat.

    With a first date set for a few days hence, for whatever reason (business or family illness) your guy is suddenly called out of town. You understand — he must go. But it happens too quickly to fit in even a coffee date to meet.
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  • The experiment

    I’m an equal-opportunity dater. I’ve gone out with Caucasian, Black, Latino, Asian, Indian, Native American and mixed-race men. Although it doesn’t always come up, I know some have been Christian, Jewish, Muslim, Buddhist, Hindu, agnostic and atheist. None of these on their own are deal makers or deal breakers. My interest or disinterest depends on many other elements.

    So it surprised me when some Black men asked me if they are an “experiment.” If going out with them was part of satisfying some curiosity of mine. The first time I was asked this I was confused, so probed.

    “What do you mean by ‘experiment?’”

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  • Playgirl centerfold returns

    (Read about our first encounter)

    A few days ago he returned from his global travels and was in my city for a few days. He remembered that my birthday is today so he decided to treat me to an early birthday celebration. He’s still handsome and buff at 61, but perhaps not as much as when he posed for Playgirl 30 years ago.

    In addition to his good looks, he’s attentive, intelligent, humble and funny. I briefly thought of abandoning rationality and suggesting a romp in the hay. I’m pretty sure he would have been game. But then I remembered that trysts are like Chinese food — soon thereafter, I’m hungry for something more substantial.

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  • Your sweetie’s and your kids aren’t similarly accomplished

    Here’s a recent question from one of our regular guy readers. I thought you might have some suggestions.

    There are usually inequalities when you are dating. One person has a more successful career. One person is better at interpersonal skills, and the other is better at technical skills. Differences that makes life interesting and the world go around.

    I have accomplished kids. All of them will graduate from college, and have the potential for decent careers. They have their flaws, but are typical middle class, suburban, kids. The kind of kids where you can share their accomplishments when friends are talking about their kids.

    I’m getting to know a woman who I think may be someone special. She seems like a decent middle-class person, but has made some bad choices in men — philanderer, alcoholic, etc. However, her kids are a lot less successful than mine. One had a promising military career until a genetic predisposition to alcoholism reared its ugly head. The younger two are content to just get by in life. In talking with her about her past relationships, she mentioned wanting the American Dream: husband, house, and kids.

    We are both past the having babies stage, but I wonder about the inequality of our families. All the kids are old enough that they won’t be living together. But, I just started wondering if the inequality will bread resentment. I can provide a husband and a house. But for kids, we will have to play the cards that have already been dealt.


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  • Crown of glory

    Hair.

    It can either be a source of pride or vexation. Women typically either love or hate their manes. If a woman’s tresses behave as she desires, she’s very happy. If not, she bemoans her bad hair genes. Sometimes both in the same day.

    What does a woman’s hair have to do with dating? A lot, it seems.

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  • I’m in love

    He’s tall — 6’3-1/2″.

    He’s dark — with a perpetual tan.

    He’s handsome — drop dead gorgeous.

    He has a deep, sexy voice.

    He’s funny, humble and adorable.

    He’s athletic — a former NFL player.

    Our 19-year age difference doesn’t seem to matter.

    There’s only one problem…

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  • Have you developed deal-breaker habits?

    I once read a study’s findings that men who were married/partnered in midlife and older lived longer than men who weren’t. The researchers explanation? That if a man has a physical ailment, he’ll let it go, not wanting to see a doctor, thinking it will clear up on it’s own. If he lives with a woman who knows about the malady, she insists (nags?) him to see the doctor. Thus, ailments that would get worse in time are nipped in the bud and healed.

    As we get older, many of us develop bad habits (like thinking something will clear up on its own). If we live by ourselves, or with a non-friend or non-relative roommate, or have friends that aren’t very forthcoming to give us feedback, it’s easy to start doing things that are unacceptable to others but we think are normal.

    This is why some people are in the “undateable” category, no matter how smart or nice they may be.

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  • The Beau Quotient

    This weekend while traveling I spent time with a gal pal. (I was staying at a hotel nicknamed “The Beau”! How fitting!). We were bemoaning our past relationships and how ignored signs at the beginning ended up dooming the relationship. Sometimes it took only months, but sometimes we’d stuck with someone for years who, in retrospect, showed all the signs of a mis-match from the beginning.

    I’d shared that I had created, but not released, a 20-question quiz called the Beau Quotient (BQ). It asks some tough questions and you honestly (if that’s possible when one is besotted) give your beau scores for each question.

    I’ve only tested this with myself, so thought I’d ask you, dear readers, to be the guinea pigs. So please download the PDF and think of a current (or recent) sweetie. Answer as honestly as you can. Tell me your refinements to the questions.

    (Gentlemen: as usual, this is focused on women. I’d guess the questions would be different if this quiz was designed for girlfriends. So you’re welcome to download it but know it’s not designed to be used across genders.)
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    Want to explore more about whether you should keep dating a guy? Get your copy of Real Deal or Faux Beau: Should You Keep Seeing Him?

  • New bonus with any purchase

    I was asked to contribute five of my best tips for dating after 40 to the new compilation eBooklet, “Tips, Tools, and Resources for the Second Half of Life.”

    This 17-page booklet includes 5 brief tips in on each topic:

    • “Rightsizing” — Getting Your House In Order Before The Crisis Sets In
    • Positive Sibling Communication
    • Creative Housing And Lifestyle Choices
    • Aging With Grace, Gratitude, And Gusto!
    • Successful Dating Over 40
    • Self Care
    • Share Your Memories
    • Keep Your Eyes On The Target
    • Financial Clarity
    • Easing The Grief Of Life’s Later Losses
    • Put Old On Hold
    • Midlife Menu
    • Nursing Home Care
    • Living A Powerful Second Half Of Life

    I’m adding this eBooklet to your gift with purchase of any of the Adventures in Delicious Dating After 40 books. Remember, you already get the bonus eBook, Attract Your Next Great Mate: Dating Advice From Top Relationship Experts with any purchase.

    If you’ve already purchased one of my books and want the new eBooklet, just email me and I’ll send it to you.
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    Get the eBooklet, “Tips, Tools, and Resources for the Second Half of Life,” as well as DG’s 152-page eBook, Attract Your Next Great Mate: Dating Advice From Top Relationship Experts with any Adventures in Delicious Dating After 40 book order.