Adventures in Delicious Dating After 40™

Category: Are you ready for Mr. Great?

  • Are you arguing your limitations?

    Midlife women sometimes passionately, convincingly, compellingly tell me why no man would be interested in dating them. “Men aren’t interested in a woman like me who has wrinkles, bags, extra pounds and hot flashes,” she may start. “They’re only interested in girls half their age. And forget anyone wanting a feisty, intelligent, educated woman like me. They are too threatened by us,” she continues. And if I let her, she’ll go on. And on. And on.

    IllusionsIn “There must be a pony in here,” I quoted Richard Bach’s book Illusions: The Adventures of a Reluctant Messiah. One of my favorite quotes from the book is,

     

    “Argue your limitations and they are yours.”

    The more you argue why no one would be interested in you, the more you convince yourself. Then you close yourself off from anyone who is the slightest bit interested. The 50-ish man who talked to you at length at the party the other night? He was very nice, funny, intelligent, and even kinda cute, but he wouldn’t be interested in someone like you. No, you’re sure of that. In fact, you saw him later talking to a 30-something beauty. But he left alone you noticed.

    What about that friend of your co-worker’s who you met at her birthday bash? He was really fun and you enjoyed bantering with him. But he was a successful executive and ran marathons, so he would probably have disdain for your out-of-shape body.

    The interesting owner of your favorite restaurant? You frequent it regularly, and he’s always nice, even flirty. But you’re sure he’s just doing that because you’re his customer. He probably has a girlfriend, but you know he’s not married because he’s not wearing a wedding ring. Besides, he’d probably rather be with a foodie — someone who understands his business.

    Do you ever hear yourself having similar conversations in your mind? You are arguing your limitations. You are stopping any possibility of getting to know these guys better and perhaps going out, even if just for coffee. And if you suggest coffee and he says he’s in a relationship, so what? You’ve made his day by showing he’s attractive, and even if the relationship isn’t revealed until during coffee, you may have a new great pal.

    So if you hear yourself arguing for your limitations, tell yourself to stop it immediately. Remind yourself you would be an interesting companion for a number of men. And open yourself up to the possibilities.

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  • What makes you feel sexy?

    In “What is sexy?” I asked you to explore what you think is sexy in a man. Now I’d like you to identify what makes you feel sexy.

    For some women, it is when they feel fit and healthy. When they neglect their workout routine, they feel sluggish and not at the top of their game. They don’t feel as confident or flirty.

    Other women feel sexy when they wear fun, well-fitting clothing that flatters their figures. Some feel sexy in tight jeans, others in more relaxed slacks, and some when wearing swingy skirts. Others find power suits bring out the best in them, sometimes coupled with lacy lingerie.

    tiger pumpsShoes are another tool. By changing footwear a woman can go from feeling matronly to red hot. A difference between a flat and a 2″ heel can change an outfit — and attitude — dramatically. And for many, thinner heels feel sexier than thick, clunky ones. Some women find strappy sandals appealing, while others love how pumps make them feel. However, for a women who’s uncomfortable in heels, flats are sexier because she’s more at ease.

    Makeup helps some women feel fetching. Applied in the quantity and style for one’s comfort level, some feel it covers flaws and accentuates positive features. Others eschew estheticians aids because to them it feels fake and unnatural.

    And for some of us, it’s our hair. While clothes, makeup and a healthy body contribute to my feeling sexy, I’ve learned that one of the biggest pieces of the puzzle is my hair. Generally, I love my hair, as it’s thick — 4 times normal I’m told. It’s naturally wavy, but sometimes I flat iron it. Other times I curl it and it bounces. I like to wear it longer — a few inches below my shoulders. But I’ve instructed my stylist to hack it back when I begin to look like those middle-aged women who wear longer hair trying to look 30 again. That is unattractive.

    Recently it slipped into the danger zone. She pruned 3 inches, which left me with an above-the-shoulder bob. It immediately affected my feeling of sexiness. Silly, I know, since I’m the same playful, flirty, fun, sensual woman who entered the salon with longer hair. But upon leaving, I felt more frumpish. I know that with the right makeup, clothes and shoes I’ll feel sexy again. And of course, I can let it grow out again. But I find it astounding what a difference 3 inches can make.

    Years ago, a different stylist cut my hair short, a few inches long. I looked like a brunette, female version of Rod Stewart, but not as thin. I cried myself to sleep. I had repeatedly told her that I needed to have some curl to my hair to feel feminine. She ignored me one too many times. That was the last time she had me as a customer.

    Jada Pinkett SmithI look at beauties like Halle Berry or Jada Pinkett Smith and notice the length of their hair — or a shaved head — doesn’t affect their sexiness. They express their mojo no matter what they are wearing or how they are coiffed. Of course, they have stunningly beautiful faces, so their hair is superfluous.

    So what makes you feel sexy? If you can articulate it, you’re more likely to make sure you feel sexy — and show it — when out on a date, or even just around town. You never know who you’ll run into at the produce section of your grocery store. Strut your mojo no matter where you are.

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  • Help your date notice his riches

    Benjamin Disraeli said:

    “The greatest good you can do for another is not just to share your riches, but to reveal to him his own.”

    In the context of dating and relationships, I read this as being willing to share your skills and talents with your date without hiding any part of you. In “Do you hide your ‘light’ from a date?” I shared how I have felt a need not to reveal many of my accomplishments with a date early on. By doing so, I’m hiding my “riches” as I’ve found many men — even accomplished ones — have been intimidated by my achievements. Disraeli is reminding us that part of our greatest good is not to leave part of who you are at the door.

    I find the second part of the quote interesting and true, too. Many people are so used to their own talents that they discount them when pointed out. Part of this is society’s frowning on pridefulness and boastfulness. And part of it is that when someone is good at something that comes naturally, or something they mastered a long time ago, they take it for granted. Friends who are concert-level musicians are modest about their skills. Excellent writer or speaker colleagues are humble when receiving accolades.

    When you help your date see where he excels, especially if it something that he doesn’t even notice, it reminds him of his special gifts. Once he is able to fully appreciate your sincere acknowledgment, it helps him own it himself. He may stand a bit straighter, have more spring in his step, or a broader smile.

    It is easy to point out someone’s shortcomings. But it takes an aware person to first notice someone’s “riches” of character, spirit, or talent. Then it takes a special skill to go beyond noticing and sincerely express your awe without fawning.

    Mother Teresa said:

    “Kind words can be short and easy to speak, but their echoes are truly endless.”

    Anytime you notice a date’s riches (not monetary), tell him what you see. Even if there is not a second date, your kind words will echo for him longer than you can imagine.

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  • When midlife dating is like high school

    Perhaps you haven’t dated in a while and now you’re beginning to go out. You meet a guy who seems great and he seems to like you too. You have a good time together.

    Suddenly you find yourself smitten. If he’s said he’ll call you tomorrow afternoon, you wait around the house all afternoon and evening hoping the phone will ring. If he calls, you’re giddy with delight. If he doesn’t, you worry about what you said or did that turned him off.

    Maybe you discuss the budding relationship with your gal pals, asking their advice. If he hasn’t called you when you think he should, you painfully debate whether to call him or not. Or perhaps you purposefully cruise places he frequents (gym, bar). Or maybe you find some lame excuse to drop by his place.

    cheerleaderIt feels similarly to how you felt in high school when you had a crush on a guy. Maybe you weren’t even dating him, but some of your feelings and behaviors are the same. In high school, you detoured by his locker between classes, lingered outside the gym after his sports practice, and ate lunch near his usual hangout. You buddied up to his friends to find out more about him and his routines. Maybe you asked him to the Sadie Hawkins dance.

    Is this healthy? The butterflies and euphoria of starting a relationship feel wonderful. However, if he isn’t as interested in you as you are in him, those feelings will quickly morph into angst.

    When it becomes unhealthy is when you find yourself thinking immature thoughts or behaving in ways that will embarrass later. A while ago I quickly became besotted with a man with whom I had dated only 3 times. I was obsessed with wanting him to call and called him more than I was comfortable. I heard myself thinking of asking him, “How do you want me to behave? What do you want me to change?” I was willing (I thought) to lose myself to be attractive to him. This is unhealthy!

    Anytime you do something that you later are not proud of, you know you’ve gone over the deep end. The trick is to realize you’re hypnotized by the fantasy of him before you act. If you find yourself wanting to do things that you know you’ll regret later (e.g., sleeping with him as a way of keeping him), find a confidant to confess your plan and ask her to talk you out of it. If she lives nearby, maybe she’ll come over and confiscate your car keys to make sure you won’t do the stupid thing.

    In her 40’s, a friend chased after men with limited or no interest. She left her husband of 20 years and moved 2000 miles to the small town in which she grew up to be near her high school boyfriend. Unfortunately for her, he was happily married and had no intention of leaving his wife. She pined for him for over a year, periodically meeting him for a drink and frequenting his haunts to see him, even if he was with his wife. Eventually, he rebuffed her enough times that she realized her folly and let go of her infatuation.

    Another time she met a man who worked on a train. Within weeks of meeting him she moved into his train car that was attached to whatever train he was assigned to. She merrily fixed it up, sewing curtains for the windows and adding her woman’s touch to make it more homey. They traveled wherever the train took them, criss crossing the country. Within a few weeks, when they were many miles from her home town, he broke up with her and she had to find her way back home.

    Perceived love can cause us to do really dumb things (in retrospect). Just like in high school. Our neediness, loneliness, or libido cause us to take immature actions. The key is to stop yourself before you do something you’ll regret. Remember, you’re not in high school anymore.

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  • Are parts of you excellent?

    Ashleigh BrillianAshleigh Brilliant writes clever sayings that make you laugh or think. Part of his, well, brilliance is that the sayings are limited to a maximum of 17 words. He is one of the most widely-quoted living writers, and also the highest-paid (per word).

    One of my favorite Pot Shots (which his musings are called) is the name of one of his books.

    I MAY NOT BE TOTALLY PERFECTI May Not Be Totally Perfect, But Parts of Me Are Excellent

    This is a good dating mantra. When you begin to focus on your imperfections (body shape, skin, wrinkles, hair, teeth, “baggage”), it is easy to forget that there are parts of you that are stupendous. Maybe it’s your quick wit, infectious laugh, great listening, continual thoughtfulness or loving compassion.

    The guy who is for you will love you for all of your parts, not just the excellent ones. It’s the imperfect bits that make you the interesting and enticing creature you are.

    And it also keeps you humble! Imagine how easy it would be to be arrogant if everything was flawless? My experience is the folks who are most arrogant have major imperfections and they use haughtiness to try to mask these failings.

    Part of Cindy Crawford‘s allure is her mole. Angelina Jolie‘s overlarge lips are considered sexy. Mona Lisa‘s smile is enigmatic. Imagine how she’d look with a big smile flashing perfect, pure-white teeth.

    Pot ShotCelebrate your unusualness. Perfection is boring and unattainable. Your atypical parts make you special, unique and rare. They are what makes you you. Which is, no doubt, excellent.

    (Click on Ashleigh’s name above and you’ll go to his web site which has various products, including postcards, books, t-shirts, mugs, pillows, and hats with his over 9000 Pot Shots.)

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  • Are you dating the same guy in different bodies?

    Portia NelsonYou may be familiar with the poem “There’s a Hole in My Sidewalk: Autobiography in Five Short Chapters” by Portia Nelson (pictured at right). In the poem, Ms. Nelson concisely illustrates how we make choices, have an unpleasant experience, and blame others. Then we learn from our experiences, take responsibility for our choices, and ultimately make different ones. I think it applies not only to life in general, but to dating.

    How is this like dating? Have you found that sometimes you’re attracted to the same kind of guy, perhaps with behaviors similar to your ex? Then you’re upset that the guys treat you like your ex treated you. And you blame them. The cycle continues. Until you wake up to your part in the repetition.

    You have probably heard the oft-quoted line, “The definition of insanity is doing the same thing over and over and expecting different results*.” It’s that way with dating. We’re drawn to certain characteristics in a man that seem familiar to us, no matter how dysfunctional. At least we are if we are unaware of how and why we keep dating the same guy in a different body over and over again. He’s attractive to us because he feels so comfortable. In fact, sometimes we may actually utter, “It felt like we’d known each other a long time.” Or, “It just felt right.”

    If we aren’t conscious, we’ll keep walking down the same sidewalk and falling in the same hole (dating the same kind of guy who treats us the same way our ex did). And we blame the guys for being losers, jerks, players, cads. It’s not our fault!

    Until one day, we get frustrated having fallen in the same hole once again! We know this time it is our fault, but it doesn’t help lessen the pain. So we keep dating. Drat — once again we find ourself in the same hole (with another guy who is self-absorbed, inconsiderate, emotionally unavailable, or worse). This time we know it is our fault. We look inside, self-reflecting, asking why we keep choosing to go out with guys who have similar patterns. Maybe we get some counseling to clear it up. Our eyes are opened.

    We continue to date. Now, however, we’ve become more discerning. We begin to ask key questions before we even meet the potential date. We know how to spot the patterns that have kept us stuck in bad relationships in the past. We say “no” more often to those who seem so familiar, but we know by what they say on the phone they would not be right for the new us.

    And finally, we meet a guy who has none (or very few) of the familiar faults. He treats us respectfully, kindly, lovingly, appreciatively. We love being with him and he with us. We have walked down a new street.

    * (This is attributed to various folks, including Benjamin Franklin and Albert Einstein.)

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  • Do your friends birddog for you?

    Lab retrieverBy “birddog” I am not referring to Labrador Retrievers, English Pointers, or German Shorthaired Pointers. However, I am referring to their ability to find and point out what you are looking for.

    The verb “birddog” is common in sales. When someone birddogs for you, s/he is providing you leads to prospects. When I was president of a sales association, we had “Birddog Breaks” at our meetings to share the kind of prospect we each were looking for, and other members would provide prospect contact info if they had it.

    When your friends birddog for you, they are suggesting their single friends as possible romantic partners for you. They may do as little as providing a name, contact info. and a brief bio. Others may more actively birddog, playing a yenta role, inviting you both on an outing and talking you up to each other.

    My point is, are you actively asking your friends to birddog for you? Are you telling them you are dating and the type of guy you’re looking for? Some people pooh-pooh the concept of friends setting you up for dates. But others know that the more people who are on the lookout for a great guy for you, the more likely you’ll find them.

    So share your quest with your pals and ask them to be on the lookout for you. Be specific with what you are looking for, otherwise you’ll be set up on blind dates with people they think are great but are in no way a good match for you. And always thank your friends for their efforts even if the date is a bust. Tell them what you liked about the guy and repeat what you’re looking for so you can train your birddog to be an even better hunter.

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  • Makeover miracle worker

    Sometimes in dating we begin to doubt our attractiveness, especially if we have a series of first dates and no second ones, or it seems difficult to get even a coffee date. I believe most women think they are plainer than they are, as I said in “You are (probably) more attractive than you think you are.” I also believe some people enter the dating scene with low self-esteem, as I discussed in “Don’t think you are damaged goods.”

    No matter how good looking you are, there is always room for a little updating or tweaking. And if you feel average-looking, it is amazing sometimes what a makeover will do for you.

    Sandy DumontLast week, my friend Sandy Dumont offered me an afternoon of her image architect services while I was in her town making a speech for a group to which she belongs. It was a wonderful opportunity to see where I could make some improvements. (When I told my sweetie I was going to become more gorgeous, his always-perfect response was, “That’s impossible!”)

    While I’ve worked with a dozen image consultants in the past 25 years, and learned from nearly all of them, Sandy’s approach was different. She worked to educate me as well as show me how I could tweak my make up and hair style to be more attractive and effective. And she suggested my colors weren’t exactly on target and gave me a pallet of new ones that would bring out my best features.

    Her wall of “before” and “after” photos was striking — some of the women (and a few men) were unrecognizable in their “after” pictures. One woman’s “before” showed a 70-something mousy woman who looked like she could be anyone’s grandma. Imagine my surprise to see the “after” pic depicting a sexy 57-year-old babe after just some modifications to hair, make up and a more flattering blouse. I knew Sandy was a miracle worker!

    So while I’m generally happy with my “look,” Sandy taught me some subtleties that I will incorporate to achieve an image that is more congruent with how I want people to perceive me.

    She has a free ezine and offers DVDs, books, webinars and online consulting, as well as workshops around the country.

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  • The date relationship test

    I’ve discovered a key relationship test. This one is guaranteed to tell you what you need to know about your guy, so I recommend using this test early in the relationship to decide if you want to keep seeing him or not.

    What is the test?

    Picking a DVD together at Blockbuster.

    Why is this such a good test?

    You will see not only if he only wants to see gory, action flicks and if he has any tolerance whatsoever for romantic comedy or chick flicks. I know, I know, I’m stereotyping. But you get mySaw point — you see how comparable your tastes in movies are, and more. Maybe you like indy films and he only likes sophomoric pics. Is he open to seeing a movie you like, even though he doesn’t regularly watch that type? And if he insists on seeing “Saw” even though you tell him you hate scary movies, he’s not listening to you.

    How do you negotiate? What if you have a difficult time finding something you both want to see? This process will tell you a lot — a very lot — about the guy you’re going out with. I’ve learned this process tells you quite a bit about your guy.

    My sweetie tells me that when a man agrees to watch a chick flick he’s really just hoping he’ll get lucky after the flick is over. Are we surprised?

    Try it and tell me how it works for you. (BTW, we ended up today with “The Holiday.”)

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  • Be willing to retry activities you think you don’t like

    Part of the fun of dating is trying new things that your date suggests. If you have the attitude of “I don’t like that” even though you haven’t tried it for 10, 20, or 30 years, you’ll kill the enthusiasm your date has for planning activities. And you’ll deprive yourself of expanding your horizons.

    Let’s say your date suggests roller skating. The last time you roller skated was 20 years ago and you remember your feet hurt and it was hard to stay upright.

    But since then you’ve taken yoga and have better balance. You also have lost some weight and have stronger legs. But even if you’ve gained weight Roller derbyand have bad knees, why not experience it again and re-decide if you like it? You probably won’t end up being a midlife roller derby star, but who knows if you might like it or not? You’re a different person now than you were 20 years ago.

    You’ll have fun in the exploration, especially if you explain to your date your reluctance and former opinion, but that you’re willing to try it again. Get his agreement that you’ll check in with each other after an hour and if your old decision still holds true and you’re not having a good time, then he won’t make you stay. Ask him to help you through your concerns and he’ll probably be by your side helping you stand up — or get up when you fall. You’ll learn a lot about him and how he approaches this activity knowing your unease. And I’m guessing there will be a lot of laughing, even if just for a short while until you determine if you like it or not.

    This retrying attitude extends beyond activities, but can include food. Did you try sushi 20 years ago and didn’t like it? But now you’re ready to try some new things, or maybe you’ve expanded your palette into other international cuisines. So why not give it a try? I love trying new flavors with someone who’s an expert. An Indian boyfriend asked my taste preferences, then ordered a scrumptious curry meal after I thought I didn’t like Indian food.

    Years ago, I decided I didn’t like camping. I’m one of those gals who exemplifies the line, “I consider camping to be staying in a hotel without room service.” We’d camped on nearly all our childhood family vacations and while the scenery was breathtaking, it was cold, uncomfortable, and a chore. Although I love the outdoors and wanted to experience the back country, I knew I couldn’t bear the weight of a full backpack. So I llamaorganized a llama back country trip, where the llamas carried the gear. The llamareros (llama handlers) did much of the work, setting up our tents, blowing up air mattresses, cooking meals, rigging a solar shower and putting up a private privy. The scenery was unparalleled. I got to experience camping with a new perspective and am glad I did.

    So the next time a date suggests something you haven’t tried in a long time, tell him of your past experience but say you’re willing to try it. Admit your concerns so he can help devise a way to mitigate them. And agree on an escape plan in case your previous decision is upheld.

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  • Beyond getting lucky: Boomer dating tips that will make even leprechauns leap for love

    leprechaunSo you’ve been unlucky in love. You think maybe this St. Patrick’s Day the luck of the Irish will rub off on you. But you’re not really interested in getting “lucky” with a one-night stand. You’d like more. You’d like a long-term relationship. So how do you begin?

    • Get out your lucky charm — you! Before you join a bunch of online dating sites, first get on your dating attitude. You’ve heard the tired — yet apt — advice to assess your positive qualities. This will help boost your confidence as, yes, it does take courage to date. There is a lot of rejection in dating so you’ve got to build up your rejection muscle. Most people are kind about telling you when they (you) aren’t a match, but a few aren’t. Don’t let it get to you. Just say, “Next!”
    • Dance a jig — or salsa. A great way to meet new people is at a singles dance. Do a Google search by “singles dance” with your zip code and see what comes up. Usually people are friendly and many singles dances encourage people to mix it up and dance with multiple partners.
    • pot of goldLook at each encounter as a pot of gold. There is treasure in everyone if you are willing to look. Not all your dates will result in a second date, but most people have something valuable inside and it will be a rewarding experience to meet them. However, if you want to keep at a minimum having to dig for relationship riches, screen potential suitors ahead of time through email and the phone. Converse several times before agreeing to even coffee. You don’t want to waste either of your time if you know there isn’t the possibility of a fit.
    • Colin FarrellStart with coffee — but not an Irish one. When alcohol enters the picture, judgment can be impaired. An Albert Finney look-alike starts resembling Colin Farrell the more you drink. So start with a short (hour or less) coffee date when you are clear headed and can rationally assess whether he’s someone with whom you want to spend more time.
    • Watch out for the Blarney. Some people have dated a lot and are as smooth as Bailey’s Irish Cream. So watch if someone comes on too strong too fast by too much flattering, calling you pet names, touching you as if you are an “item” on the first date, or going for a passionate kiss within minutes of meeting you. Best to head for the hills as if chased by snakes!
    • Progress slowly to corned beef and potatoes. Don’t start with a dinner date. If you haven’t pre-screened the person and met for coffee, a dinner date can be excruciating if your date continually complains about the ex, talks incessantly, or swears a blue streak. Only accept dinner for a second date, not a first.
    • shillelaghDon’t flail yourself — or your date — with a shillelagh. If it doesn’t work out, don’t beat yourself up, nor blame your date. Be grateful that you quickly found out it wasn’t a match and move on. Let it go. Get back into the dating pool and try again.
    • Wear green. Unless, of course, you want to be pinched!

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