Adventures in Delicious Dating After 40™

Tag: Dating after 40

  • “Pimpin’” — Dating multiple guys

     

    “Save a boyfriend for a rainy day — and another, in case it doesn’t rain.” —Mae West

    I’ve found that successful dating requires juggling several men at once. It is like sales, you have to have a number of prospects in the pipeline. I frequently date several men in the same time period until two of us decide to be exclusive or one of us decides to move on. If you only date one at a time, it takes too long to get the next one in the pipeline.

    When I was explaining this to my teenaged nieces, they said I was “pimpin’.” Now hold your hat — their definition of a pimp was not the same as mine. It merely means dating around. Let’s be clear here that dating around does not mean sleeping around. You can date multiple people and not sleep with any of them. In fact, I’d recommend you not sleep with any of them until you decide to be exclusive and you both agree that means letting go of all the others you’ve been seeing. It is not wise or safe to be a “player.”

    Dating around takes special skills. You have to remember the guy’s name when you’re with him, unlike the time I was halfway through dinner and couldn’t think of my date’s name (it was a first date). I have been told by a guy pal that when a man can’t remember your name on a date, he calls you “sweetie.” You think it’s endearing; he gets off the hook.

    You also have to remember other details that he’s shared, otherwise you’ll ask the same things over again and he’ll think you didn’t pay any attention at all. I’ll share an easy way to track this in another posting.

    You have to have the discipline to not talk about your other guys while on a date. This is déclassé. While you can imply that you are seeing others, don’t throw it in his face. He may think you are slutty.

    But dating around gives you an opportunity to have multiple activity needs met. One likes foreign films, another opera. One likes to hike, another is a tennis buff.

    BTW, he may be dating around, too. Clarify this on the first few dates just to be sure you’re on the same page. When I do this, I always ask if he’s sleeping with anyone. Multiple sex partners increase the risk of STDs. I recommend not sleeping with anyone til you’ve decided to be exclusive, then you both get tested for STDs before going further.

    So dating around has its pros and cons. I find the pros outweigh the cons, and open, honest communication is best if you are going to date others simultaneously.

  • What is sexy?

    “Sex appeal is 50% what you’ve got and 50% what people think you’ve got.” —Sophia Loren

    In my online profile, I used to describe myself as sexy. I took it out. Why? I realized that while I feel I am sexy, it is totally subjective. What if the guy doesn’t find me sexy? Will he doubt other things I say?

    What is sexiness? To me it is a confidence, a strong sense of self, not arrogance. It doesn’t have to do with body size or shape or facial beauty. I’ve known people who were sexy but not particularly physically attractive. A friend of mine is a burn victim, having scars over most of his body, including his face. Yet he is a babe magnet. I rarely see him without a beautiful woman — or several — surrounding him. He’s been married three times!

    Do you think you are sexy? If so, do you allow it to show? Do you wear clothes that show off the best parts of your body without looking slutty? Do you smile, flirt and play with men? Does your walk show confidence? Do you put your best foot forward in public? These all contribute to that mysterious “sexiness.”

    What do you think is sexy in men? I am partial to easy smiles, long-sleeved shirts with the sleeves rolled up, a great fitting suit with an impeccably tied tie (small knot), goatees, good posture, a tuft of chest hair peeking out of an open-collared neckline, intelligence, humor, kindness, strong biceps and chivalry. I once went out with a man because a pic in his profile showed him with a great smile and biceps the size of my thighs. (OK, nothing is as big as my thighs, but you get the picture. Unfortunately, the in-person version was not as enticing as the picture.)

    Describe what you think is sexy. This is not all the attributes of your perfect mate, but what you find sexy. If it is personified in Richard Gere, Taye Diggs, or Tom Cruise, what is it that makes them sexy to you? When you articulate it clearly, it will be easier to spot. Don’t cop out with “I know it when I see it.”

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  • Getting naked with him the first time

    “According to a new survey, women say they feel more comfortable undressing in front of men than they do undressing in front of other women. They say that women are too judgmental, where, of course, men are just grateful.” –Robert De Niro

    Many mid-life singles haven’t been intimate with someone other than their long-term mate for a long time. A common concern is that your body is not the same as it was when you were younger. You have what Bridget Jones called “wobbly bits.” So the prospect of getting undressed with someone is unnerving. So much so, that it may prevent you from putting your toe in the dating pool.

    Hopefully, you don’t choose to become intimate with someone until you have dated him for a while. At that point, it is really a moot point because he will have seen you in different attire so knows your body’s pros and cons and will love you for you, and not focus on your less-than-perfect body parts. As one male pal put it, “When you’re naked we know we’re going to get sex, so we don’t focus on any imperfection. We’re just very happy!”

    My first post-marriage naked experience was with a man I’d been dating for a while. He was 100 pounds overweight so I had little concern he’d judge my larger-than-normal bumps and curves. I was right. In fact, I learned that some men love women who are, as one friend put it, “umpa lumpa.”

    If a man criticizes you when you are unclothed, that is a good sign he is not the right man for you. Even if you are not happy with your body, he should have the good sense to shut up, even if you are complaining about your stretch marks, cellulite, chubby thighs, etc.

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  • Don’t initiate

    Chatting with a friend yesterday, he observed that dating for woman over 40 was different than for women under 40 because of the mixed expectations. Many mid-life women have had career success because of their assertiveness — sometimes even aggressiveness. While that serves them in work, men don’t typically want an aggressive woman in their personal lives.

    However, my friend continued, younger women are expected to be aggressive in both parts of their lives. He believes younger men expect and accept that in a romantic partner.

    I think it’s difficult for most over-40 women to compartmentalize their lives and behavior to be aggressive at work but not in dating. While I have been successful in business by initiating contact with potential clients, in my personal life I have a do-not-initiate policy.

    With few exceptions, I don’t send the first email. I also never initiate the first date. I wait for the man to say “Shall we get together?” If he is not interested or assertive enough to ask, we aren’t a good match. One man talked to me several times a week for a month and never asked me out. Finally, I told him we weren’t a match, but he still emails periodically.

    While dating sites encourage you to make the first move, 90% of the men I contacted first either didn’t respond or said they weren’t interested. The few who responded positively ended up not being good matches.

    Most men still want to be the pursuer. After the relationship has begun, it’s usually OK to call him, or suggest an activity. But let him take the lead. If he doesn’t, he isn’t a match.

  • 50 ways to leave your lover? 4 ways NOT to leave your suitor

    If you know it isn’t a good match, you owe it to him to tell him and then either move on or become friends. But do so graciously, respectfully and gracefully, no matter what. Here are four ways NOT to let him know.

    • Via email — if you’ve dated him more than a few times, have the guts to tell him that you aren’t going to see him again in person, or if that’s not possible by phone. I had a lover break up with me via an email after we’d dated exclusively for 7 weeks. He said he was too cowardly to do it in person! It was disrespectful and hurtful to not do it in person when we’d just seen each other the day before.
    • After only a few minutes — After 10 minutes one guy told me that he wasn’t attracted to me so he was leaving. On one hand, good that he didn’t waste either of our time. But he could have been more graceful than saying “I’m not attracted.” How uncouth!
    • Yahoo messangerBy IM — This is the modern version of the “Sex and The City” Berger break-up Post-It to Carrie. Tacky. A guy I had been dating for 6 weeks sent me an Instant Message breaking up with me — when he knew I wouldn’t be around to read it until later. Essentially, it is as classless and spineless as an email.
    • AWOL — Not returning emails or voice mails. I’ve had two guys do this, one I’d dated for 6 weeks. After talking 5 or 6 times a day for 6 weeks, he suddenly didn’t respond to any emails, IMs or voice mails. He’d left some clothes at my house that I wanted to return to him after I didn’t hear back for a few days, and he still didn’t respond. I left them on his front porch, as there was not much else I could do.

    Have the courage and decency to be gently honest when you release this person back into the dating pool. You will feel better about youself, and you’ll leave him not hating you.

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  • Start with coffee

    StarbucksNew online daters have shared that they are concerned about accepting a date with someone and as soon as they meet him, they know he is not a match. If the plan is for dinner, dancing, lunch or hiking, they know the are in for hours of making polite conversation with someone they know is not their type.

    The solution: Start with coffee.

    If you have not met this person, no matter how charming and fun he sounds on the phone or in emails, start with coffee. If you meet and hit it off, coffee can easily extend to lunch or dinner. I’ve had 5-hour dates that started with coffee and went into lunch or dinner.

    Coffee is a minimal time investment: 30 minutes to an hour. You can be polite to nearly anyone for 30 minutes, can’t you? Even if you meet and know there is no attraction, fight the urge to exit after 5 or 10 minutes. Unless he is totally offensive, stick it out for 30 minutes. You may make a new pal, or have a gal pal who he might be good for.

    I’ve dissuaded guys who wanted to start with dinner and dancing. I’ve learned from experience. I now say “Let’s start with coffee and see if we hit if off and want to spend more time together. Then our second date can be that nice dinner that you’re suggesting.” They understand and agree.

    If you want to meet after work, a drink would seem logical. However, it is a tad awkward as it gets toward dinner time to decline an offer of dinner if he thinks it is going well. But if you want to bail, don’t do dinner. Extricate yourself as gracefully as possible: “I’m sorry, I must be going.” “I have a big day tomorrow, so want to get ready for it tonight.”

    This is why coffee is the perfect solution. For some reason it is less of a problem to leave when your coffee cup is drained. So don’t set up yourself to suffer — agree to start with coffee.

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  • One ringy-dingy — making the first call go smoothly

    phoneIt seems many people have difficulty with the first phone call. If you are initiating the call, you may procrastinate because you don’t know how to start.

    Nowadays, men know that some women don’t want to give out their number, so they give her their number. This gives the woman more control over who they call and when. but once you’ve called, with caller ID, he has your number.

    I like to call first from my cell phone. If you give your land line number, anyone can easily put it in Google and find out not only your street address, but a map to your home!

    1. Don’t put off calling for more than a few days after getting the person’s number. If you do, it shows you’re either not very interested or too busy to see him. Some waiting is good, but too long and he’ll move on.
    2. Review the person’s profile before you call. In fact, having it in front of you is a good idea. If he calls you, quickly find his profile if you are in front of your computer so you can be more conversant about him, his interests and life. It is annoying to be asked “Are you divorced,” “Do you have kids?” “What city are you in?” and other data that is in my profile.
    3. Listen carefully. This means you shouldn’t place the first call while driving, grocery shopping, or other tasks that may distract you. I find it rude if someone I haven’t talked to before tries to multi-task during the call. It doesn’t make a good first impression. If he calls you and you’re caught in the middle of something, ask if you can call him back within a certain time period.
    4. Don’t interrupt. If you tend to be an interrupter, keep it in check, especially during the first call. I’ve declined dates with guys who were blatant interrupters as I find that a difficult habit to deal with.
    5. Ask questions, but don’t interrogate. Think of questions that will help you know the person better, beyond the basics, of what do you do, where do you work, etc.
    6. Share air time. A person who hogs the conversation is a bore! Make sure there is give and take, so he feels like you are interested in him.
    7. Take a deep breath and just dial!

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  • From hurt to flirt

    When my husband of 20 years left me I was stunned. I didn’t see it coming. After crying in a fetal position for a week, I gifthad a talk with myself. I decided I was going to see if I could turn around the situation into something positive. I had a knack for doing so in other situations, but none quite as debilitating. I began to see if I could find the gift in this life-changing surprise.

    I thought “What could be the opposite of ‘My life is over.’?” How about “He has released me to explore the untethered life as a single women.” It took me a month to say it without laughing.

    At first the thought of being middle-aged and overweight terrified me. Who would possibly think I was attractive enough to date? But I began chanting my mantra to myself daily. I began to flirt with men of all shapes, sizes and ages, straight, gay, married, single. It was fun!

    Soon men were initiating the flirting. I became more playful and had a lot of fun. I began to see I could be attractive — at least attractive enough for someone to flirt with. I began having the life of my mantra — I was living the untethered life of a single woman and having a blast doing it.

    What are you saying to yourself about dating that is negative — “The only men I meet are losers.” Or “All the good men are gay or married.” Or “I’ll never find my soulmate.”

    See how you can change it around to be inspiring: “The men I meet are extraordinary, successful, kind and caring.” “There are abundant good, straight men longing to meet a good woman like me.” “My soulmate is just around the corner and is looking for me as hard as I’m looking for him.” The more you chant your mantra, the more quickly it will come true!

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  • How to say “thanks but no thanks” to online winks, flirts and teases

    When someone is not a member of a dating site — or they are lazy — they float a trial balloon by clicking on “Wink” (depending on the site, these are also called flirts or teases).

    I am convinced some men do a rudimentary search by criteria such as “breathing” and “lives on the planet Earth” and then wink at every woman who comes up. I say this because I get winks from men who are not only not in the same area, but are not in the same state or country. This is like fishing with a net, verses the more skill-based fly fishing — they are just seeing who will respond to their broad contacts.

    I’ve had winks from men 30 years younger, 5 inches shorter, who are far below my other criteria. On one level, I admire their boldness. On another level, I want to say “Do you really think the Goddess would consider going out with a 27-year-old movie usher who lives with his parents and rides his bike to work because he doesn’t have a car?”

    So what to do? Do you just ignore them? If you get a LOT of winks — say 5 or more a day, then you have to. But I like to respond to every contact, no matter how lame or mismatched. So I have a macro saved with a polite “no thanks.” By typing 3 letters I get the following:

    Thanks for your wink.

    I’m sure you are a nice guy. I appreciate your interest in me, however, I don’t think we’d be a good match.

    Good luck in your search. I wish you the best!

    I’ve even been thanked for how I say no! It seems so many people don’t respond to any contact — whether wink or email — that any response is considered polite and classy.

    Create your own polite message so you can just cut and paste.

  • Shopping for men

    Dating life can be brutal. You make an effort to look nice (I call it getting “dated up”) to meet someone new, then he either doesn’t contact you afterwards, tells you he’s not attracted to you or there’s none of that elusive “chemistry.” You have to have perseverance and hope that someone for you is right around the corner — or in the next email.

    I’ve found dating to be a lot like clothes shopping. First, you have to shop where you know there is a large pool of prospects, which is why people shop at malls. When I conduct an online search, I call it “shopping for men.” On the best dating sites, you can search by important criteria (e.g., age, height, location, income, education, smoking/non-smoking, even activity level). Just like clothes shopping, you know the size, colors and style you want.

    And just like clothes shopping, you have to look at LOTS of possibilities, even when you’ve narrowed it down to a certain brand and size. It is easy to get frustrated.

    After a day of shopping with no buys, do you say “There are no good clothes out there?” Or “All the good clothes are taken!” Or “All the clothes I looked at are losers. I’m giving up.” No! How silly.

    Would you ever consider stopping shopping? No! You keep shopping because you have hope that you’ll find something you’ll love. That will be comfortable and fit and you’ll feel great in. Same with guys.

    However, it can get wearisome going on a bunch of dates with guys who on paper seem a good match, but in person there’s no spark. You can doubt your attractiveness, or think you are too picky. If you find no one you can entertain the possibility of going out again with, then perhaps it is time to reassess your criteria.

    For example, I thought I must have a college graduate. Then I dated a delightful gentleman who didn’t complete college as he was recruited to be a CEO while in college. He is very bright, but was tapped before completing his degree. I then found other fun men who were successful despite not having a degree.

    Did I “settle” for less by lowering my criteria to allow for those who didn’t complete college? I don’t think so. If you’re having a hard time in your shopping activities, consider if some of your criteria could be altered.

  • Dating is like Baskin-Robbins

    Baskin-RobbinsI compare my philosophy of dating to visiting Baskin-Robbins where I ordered vanilla for 20 years (maybe it was Rocky Road at the end!). While I enjoyed vanilla, I want to try new flavors. And I didn’t want to jump from vanilla and make a commitment to butter pecan without having tasted a little pistachio, chocolate, mint chip, and more.

    So I made a list of men I’d like to “try” (just like I “try” ice cream flavors).

    I like smart men, so wanted to “try” a lawyer, doctor, CEO, and venture capitalist. I like large men, so wanted to “try” an ex-pro football player and ex-pro basketball player. I love men with accents, so wanted to “try” some who came from foreign countries. You get the picture. I landed dates with all of the above and many more.

    ice cream coneIn the beginning I even gave my guys names of ice cream flavors. Butter Pecan for the PhD in electrical engineering because he was interesting and refined. Double Dip Chocolate with nuts for the fun-loving, 6-foot-9, black former pro-basketball player. Bubblegum for the 32-year-old movie date. Jamoca Almond Fudge for the Caribbean-born gentleman. Cafe Olay for the Brazilian salsa dancer. Passionfruit for the good kisser. Chunky Monkey for the chubby, hairy one. Hunka Burnin’ Fudge—well, you can guess that this one was eye candy!

    But I quickly ran out of nicknames, as I had more guys than Baskin-Robbins had flavors. Even borrowing from Ben and Jerry, I was burning through flavors faster than a double dip on a sweltering August day.

    So I encourage you to “try” dates with men you might have turned away if you’d strictly adhered to your list of desired traits. Some of my favorite treasures have come from going out with men who wouldn’t have been on my radar screen before. (A 6-foot-9 guy? “No way,” I used to think. But Double Dip Chocolate has become one of my dearest pals—as well as one of the best kissers I know!)

    So don’t limit your choices of flavors too much. Yes, those you date need to have the same values as you. But who cares if a man who lists himself as “athletic” in his profile is 40 pounds overweight? Extra weight can be shed, but integrity, intellect, thoughtfulness, respect, and caring are embedded. You can’t change that.

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