Adventures in Delicious Dating After 40™

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  • He makes you laugh — is that enough?

     “We cannot really love anybody with whom we never laugh.”
    —Agnes Repplier

    Women list the number one thing they want in a guy is “someone who makes me laugh.” While I agree this is important, it is not the over arching criteria on which to base a relationship.

    Yesterday I was contacted by a guy who had emailed me several months ago. I had sent him one of my nice “thanks but no thanks” emails. I couldn’t find his online profile, so wrote back to ask for his handle. Along with his screen name, he sent me this:

    “There are a lot of things missing in my profile that I would like to point out, so since bullet point presentations is what I do on a regular basis, I thought this would give you a better idea of who I am.

    1. My business is doing very well, so I am financially secure. Since all of this terrorist stuff started, they basically leave the drug dealers alone. As a result it would probably be several months before I try to borrow money from you.
    2. I am emotionally available. Ever since I was acquitted of my ex-wife’s death, all of the issues of emotional baggage are safely at the bottom of San Francisco Bay….literally.
    3. I am of upstanding and forthright character. This can be verified by the type of people that are frequently seen around me, judges, attorneys, miscellaneous members of law enforcement and parole officers.
    4. I have been clean and sober for almost six weeks now. Unfortunately I need to admit that I have put on a few pounds since giving up heroin as my diet aid.
    5. I was given a clean bill of health by the instructor of the anger management course that I was required to take (these court ordered things are so annoying). The instructor mentioned that he has never seen such a radical and permanent change in any student ever. Ironically I was punching him when he said that, but you get the general drift of what I’m trying to say.
    6. As a father, I have instilled excellent values into my children. My son was recently arrested and refused to rat out his co-defendants. Even after they offered to let him walk. Makes a father feel proud to see his son living by a code. My daughter has really taken my business sense and gone to a whole new level. She currently has about eight girls working for her. They are doing great. I don’t get to see her as often as I like, do to her business being only legal in Nevada. She has considered moving back to California, but seems to think L.A. is the appropriate place. There appears to be some significant market share since Heidi Fleiss left the business.

    “Ok…so I am trying to make you laugh.”

    Did he make me laugh? Yes. Did I agree to a date? No. There were too many things in his profile that were unappealing that even a great sense of humor couldn’t overcome. However, if there was only one or two things that weren’t a fit, I would have considered it based on his humor and persistence. So humor can tilt the scale in a guy’s favor. But it alone is not enough. Be clear on your criteria and if humor is one item, don’t allow it to overshadow all others.

  • “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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  • Safe online dating

    A gal pal said she was afraid to date online because of safety issues. It’s true that online you don’t know much about the guy. But that is true if you meet him in a store, bar, on a singles hike or dance. So there are some precautions you take no matter where you meet someone, but especially with online connections.

    • Set up an email address that doesn’t include your name. You can set up free email accounts through Yahoo!, Google, Hotmail and others. Make sure you don’t put your name in the “from,” just your handle. The reason you don’t want to put your name in the “from” is someone can easily Google you and in some cases, find out where you live or work, go to church, or frequent other places if there is a posting with your name on a web site. I’ve found out where guys worked and lived, complete with a map to both, by a little Google sleuthing.
    • Only give your cell phone number. Did you know that someone can find your home address and map if you give them a listed landline number? So if you give him your number, only give your cell. And to be even safer, take his number but don’t give him yours.
    • Only meet him in public places for the first few dates. When I’ve made exceptions to this rule, I’ve been sorry. Not because of safety concerns, but because it is harder to extricate yourself from an uncomfortable situation or send him home if things get too personal. So now I only meet him in a public place for the first few dates.
    • Don’t get in the car with him on the first date. He may seem fine at first, but you are totally at his mercy when you are in his car. Always take your own car, no matter how nice he seems. If he pressures you or tries to make you feel silly for wanting to have your own car, you know it’s time to leave. Same with him wanting you to drive him somewhere. Don’t do it, no matter how trustworthy he seems. Ninety-nine percent of the time it will be fine, but you don’t want to worry about that 1 percent that creates a problem.
    • Ask about him at places he frequents. I learned a potential suitor worked at a company where another friend worked. After we set up a lunch date, I called my friend. She said she thought he was married. She checked around and found out that yes, he was. I cancelled the date. Another guy attended the same Rotary as a friend of mine. I asked her about him and she said he was a good guy. Had she said anything negative, I would have rethought if I wanted to meet him. If I did, at least I would know my friend’s take on him.

    While the above seem common sense, I’ve ignored each one. Now I don’t. Not that I’ve been in any dangerous situations, but I’ve realized I could have been. So keep your guard up for the first few dates. Even after that, someone could turn out strange, but I find most guys are on their best behavior for the first few dates, then their true nature begins to come out. So don’t make exceptions to the above until you are pretty confident he is a good guy.

  • 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.

  • Dating as networking

    I’ve been pleased to meet some wonderful men in my dating adventures. Sometimes I’ve been able to connect them to others in my life.

    A year ago I had one date with a charming, educated, articulate man who consults on doing business in Africa. We kept in contact after the date, even though he lived 3000 miles away. A few months later a colleague told me she was looking for a CEO for a new company to do work in Africa. I connected them and he interviewed for the job.

    Also a year ago, I had one date with a man who helps third-world entrepreneurs obtain micro loans. When he focuses on Africa, I’ll connect them. In fact, I’ve become involved in his non-profit even though we’re not dating anymore.

    I dated an interesting, intelligent man a number of times early in my dating career. He is in my same industry. We stayed in touch, have lunch periodically, and now we regularly bounce ideas off each other.

    However, don’t expect it to always work. I had one date with a man who owned a roofing company. When I needed a new roof last fall I called him to see if he would give me a bid. Unlike the other roofers I called, he quoted me $100 to give me a bid! I passed. Obviously, having had a drink with him earned me no special treatment.

    So even if it doesn’t work out romantically, you are expanding your network! You never know when this will be of value.

  • Do you have the right datewear?

    Do you have the right clothes to wear on dates — datewear? I think it’s especially important to have the right kind of attire for the first meeting. You know how important first impressions are — and how you dress says a lot about you.

    I’ve had dates show up in unironed shirts and dirty jeans. Yuck! I don’t expect him to wear an Armani suit on the first meeting — just on the second date. Just kidding. I do expect him to make some effort to look nice, just as I do. In fact, unless we are going to garage sales, the beach or hiking, I expect him to show that he cares about how he looks.

    So what to wear? If you haven’t dated in a while you may have to buy some datewear. This is tops, slacks or skirts that are somewhat casual, but are flattering and current. Your old jeans and t-shirt just won’t do, unless you want to attract a man who wears old jeans and t-shirts too, or you have a killer body and look great in jeans and t-shirts. Most of us don’t.

    You don’t want tops that are too tight or too revealing. I call cleavage-plunging tops “slutwear.” You might show just a hint of cleavage, but don’t go all Pamela Anderson unless you’re a starlet. Your date will think you are loose, even though cleavage is now considered an accessory.

    You may need to get new jewelry, belts and shoes if all you have is workwear and sweat clothes. If you have trouble pulling it all together, ask a stylish friend to help you, or make an appointment with a Macy’s personal shopper. You really only need one or two outfits. You will be meeting a lot of guys for first dates, fewer for second, and even fewer for third dates.

    Think about how you want to be perceived — approachable, confident, vulnerable, sexy. You only get one chance to cement that first image in his mind, so it’s important to be strategic. I often wear a casual skirt on the first meeting, as I think it’s more flattering on me than slacks. What do you look best in? Make sure it’s clean, ironed and ready to knock ’em off his feet!

  • They come, they go

    When a friend asks about a potential suitor I’ve talked about but is no longer around, they seem surprised when I say “He’s gone. They come, they go.”

    This is how it is in the dating world. You see someone a few times, then they lose interest or move on, but don’t bother to tell you what’s going on. I’ve learned not to take it personally; it just isn’t a good match, even if I thought it might be worth more exploration.

    I try to practice (but am not always good at) the Zen concept of non-attachment. I enjoy the time I am with someone, and if we continue to see each other and we’re both enjoying it, great. But if one of us decides it isn’t a good match, then fine. It truly isn’t a good match unless both people feel so. I work hard not to leave a guy hanging, so will either tell him personally, or if we’ve only met once, through an email. However, I find many, many guys just do a David Copperfield — they vanish.

    I may write him an email if I am interested in staying in touch, but I most likely won’t call. I figure he’s moved on. He knows how to contact me and if he’s drawn to do so, he will. But I send a nice email to let him know I figure he thinks it isn’t a match and if he’d like to reconnect at some time, he’s welcomed to do so. Some guys think if too much time has passed, they are embarrassed at trying to rekindle a relationship, so I want him to know the door is open, even if just as pals.

    It can be hard to practice non-attachment if you are strongly drawn to someone. But if you become too attached too early, it leads to demanding, needy, controlling, jealous behavior — which will drive the subject of your desire to leave in a flash. So just enjoy what you have and you will, in fact, be more appealing. He will want to be around you because you have no expectations that he will call the next day or take you out the next weekend. It actually makes him want to be with you more.

    But if he disappears, don’t hunt him down. Just know he wasn’t a good match for you and say what I’ve said very, very often: “Next!”

  • Flirt your heart out

    “Flirt — a girl whose favorite man is the next one.” —Anonymous

    After spending the day together shopping and dining, a friend told me she marveled at my ability to flirt and said I should teach classes on flirting!

    I hadn’t really thought about it until she said it. Yes, I am friendly, I smile at both men and women, and I say positive things to men. And sometimes I more overtly flirt.

    Take yesterday. I was traveling and commented on the skycap’s Southern accent. “Where’s your accent from?”

    “Texas, ma’am.”

    “You don’t sound like you’re from Texas. You don’t have that twang.”

    “Thank you, ma’am. I hate my accent and have been trying to lose it for years.”

    “Oh, no. It’s charming. No need to lose it.” I smiled.

    Big smile: “You just made my day.”

    “I’m glad. By the way, is Tommy still here? He had braids and his son was also a skycap.”

    “I’ve worked here for many years and don’t know a Tommy. However, my son used to work here and I had braids until recently. My son is now in college.”

    “You don’t look old enough to have a son in college.” I smiled again.

    Big smile: “Wow! You’ve made my week now! Thank you very much. I hope you have a great trip.”

    With that, I walked away and we both had smiles on our faces.

    Did it cost me anything to say what I said? No. Was I lying? No, nothing I said was a lie. Did I want anything from him? No. Did it make him feel better? Absolutely!

    So if you don’t already, practice flirting. Now don’t flirt with coupled men who you think will misinterpret it. I flirt with my gal pals’ husbands in front of them. But I include them in the flirt: “Annie, you really scored snagging such a cute husband.” “Laura, your hubby is so buff how do you keep your hands off him?” “Sharon, you must be so proud to have such a successful husband.”

    Practice on waiters. Two gal pals and I were being seated by the waiter who said “And here is a special table for three beautiful women.” I responded, “And we get to be waited on by a handsome waiter.” Was he handsome? Not really. But he started it! I just wanted to continue the theme. I doubt that many women told him he was handsome. Did it cost me anything? No. And we got the best service ever — plus he comped us dessert!

    So flirt with abandon with strangers. Practice with flight attendants, waiters, hotel staff, anyone who you feel won’t think you mean more. It’s fun. It will make their day, and yours, and when it comes time to flirt with someone who interests you, you’ll feel comfortable, not nervous.

  • In search of the elusive good kisser

     

     

    “A man’s kiss is his signature. ” —Mae West

    I’ve been surprised by the lack of good kissers in my dating adventures. Granted, sometimes it takes a while to actually get a romantic kiss — if ever. It took 6 dates with one guy before I got a “real” kiss — something beyond a peck. On the other hand, several men have greeted me with a deep kiss as if we’d been dating for a while. The latter is not my preference. I like to get to know someone and be drawn to him before I want to explore further, if you know what I mean.

    Two men have told me they are planning on kissing me upon meeting. This does take some of the anxiety out of “will he kiss me?” — sometimes it seems premature.

    Several stopped me while we were walking to plant the first kiss. Another, charmingly leaned over when he arose mid-meal to go to the men’s room, “I need a little kiss to tide me over while I’m away from you.” It was cute and worked to get me to hang out with him more.

    “Whoever named it ‘necking’ was a poor judge of anatomy.” —Groucho Marx

    On thing I’ve noticed is if a man says in his profile that he’s a good kisser, he often is not. With only one exception everyone who said he was a good kisser actually wasn’t.

    In fact, if his profile says he is handsome, he often is not. I’ve sometimes wanted to ask “Who, besides your mother, has told you that you were handsome?” If he says he is a gentleman, he may think nothing of trying to bed you on a first date. And if he says he’s a great lover, well, let’s just say I don’t let those guys prove their claim.

    So I’m surprised that men in middle age don’t know how to kiss better. One man I dated for six months was too much too fast, no kissing foreplay. Another was so sloppy I needed a napkin afterward. I could go on and on. I’ve been tempted to dog-ear the kissing section in “Mars and Venus in the Bedroom” for some suitors and put it in a place I know he’ll see it.

    A friend pointed out that perhaps other women have liked how these guys kissed. Or maybe they’ve just never had feedback. How do you say to someone “You aren’t a good kisser”? That’s like saying “You aren’t a good lover.” I’ve tried modifying their behavior by giving them positive feedback on the parts I like: “I love it when you nibble on my lips,” or “I love the anticipation of our kisses when you kiss my face first.” Some learn. Others don’t.

    I must admit I’ve hung out with some gentleman callers longer than I should have if they were good kissers. It’s an elusive — but I hope not dying — art.