Adventures in Delicious Dating After 40™

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  • Assume there are other women

    Most of us who employ online dating adopt a “don’t ask, don’t tell” philosophy about dating multiple people simultaneously. At least until we’re ready to get more serious.

    When I am seeing a few guys, I don’t ask the date I’m with if he’s seeing others because I don’t want him asking me. I assume he is, and make decisions about how close to get to him based on that assumption. If he asks me if I’m seeing others, I’ll tell him the truth. I’ll then ask him.

    Why don’t I want him asking, at least in the early few dates? Because I don’t want him to say he’s not dating others and he wants us to be exclusive. Although I’m honest, it’s a difficult conversation to have if he is a one-woman-at-a-time guy and I’m not ready to reciprocate. Some men don’t date much and they don’t have as many options as you might. You don’t want to limit your activities too early, before you’ve decided you want to focus on him.

    I don’t believe many midlife men have the organizational skills or time to see more than one woman concurrently. They are busy with work, hobbies, perhaps kids and for many of them to squeeze in time to see one woman is difficult, let alone two or more. My friend Bruce thinks I am naive. He says most men can balance more than one woman without a lot of trouble. Women forgive them for not remembering details of their lives. So they don’t put much effort into where a woman’s parents live, where she grew up, her best friend’s name, etc.

    I discovered a guy I was dating was still seeking others by looking at his profile online and seeing that he’d logged on within the last day or two. He can see my activity as well. Since we hadn’t promised exclusivity, it wasn’t a problem, but it did let me know he wasn’t focused on only me. It also said he wasn’t completely happy with our relationship so was hunting.

    One guy was so brazen he used my laptop to log onto his Match.com account in the kitchen while I was fixing him dinner! That was tacky! It triggered an interesting discussion about where each of us was about exclusivity.

    Be careful how you ask the question. If you say, “Are you seeing anyone else?” he can honestly say “no” if he is not actually dating anyone else. However, he could be in heavy flirt mode by phone or email with one or more women, he just hasn’t had a date with them yet. So even though there’s no one else at the moment you asked, that could change tomorrow after he’s set up dinner with another gal. If it’s important to you that he’s seeing only you, in addition to the question above, ask, “Do you plan to date others while seeing me? Do you plan on contacting others while we are in this exploratory stage? How are you responding to emails from others? Do you believe in dating several women simultaneously?” The challenge is to elicit the information without it seeming like an interrogation.

    nooseMy philosophy is to not bring up the conversation, but to continue to meet others until he asks me about exclusivity. If you ask him, some men feel it is a noose tightening around their neck. If you want to set some parameters around physical activities until there is exclusivity, tell him so. It will have him assess how serious he is about you.

    Don’t ever assume you are the only one unless you’ve had a candid conversation with your guy.

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  • The sexual audition

    Some people feel it is important to discover if you are sexually compatible before investing a lot of time developing a relationship with someone. Others feel that sex is something that should happen after a firm foundation of trust and caring has been developed.

    auditionIf you are in the first camp, then your first time having sex together is a sort of audition. You, and perhaps your partner, are assessing if the other is a good lover, sexually generous and satisfying. What is the proof? There is generally only one way you (or he) determines if there is a match: if whoever is making the determination is satisfied, although some include the others’ satisfaction as part of the criteria.

    The rub is that if one of you has a challenge that prevents you from achieving satisfaction, the other is often blamed. Certain medications can impair one’s libido and performance. A man who has ED or can’t be satisfied blames the woman. If he experiences this more than a time or two, he ends the relationship. He will either become obnoxious to make the woman break up with him, or he’ll walk away, making up lame excuses.

    Perhaps he is embarrassed that he can’t perform. Or it takes him a long time. Or he has to start over several times. Or little he does seems to excite you. Or it’s not enough.

    It can be frustrating because you’re drawn to each other enough to want to get closer sexually. If you both are willing to work on it, to talk about it without blame or embarrassment, sometimes the situation can be changed. But if this is a part of a romantic relationship that is important to you, unless something shifts, perhaps it’s best to admit that the audition is a failure and move on.

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  • Get back on the horse that threw you

    After a distasteful or painful dating experience, it’s tempting to stop dating for a while. In fact, some people find a heartbreaking experience so odious that they swear off dating for years.

    While it’s a good idea to take a break to heal your wounds, if you go too long you lose your rhythm. You get rusty. It can affect your self-confidence. Yes, it is like riding a bicycle, the skills comes back. But sometimes it’s hard to get your head back in the game.

    horse My strategy is to take a little time to regroup, assess the lessons, refine what I want — and don’t want, but then get back on the horse that threw me. If you don’t, you’re saying the setbacks win. You’re letting a guy get you down who has undeveloped communication skills, lack of integrity, emotional unavailability, immaturity or who just realizes it isn’t a match. You’re letting his actions determine your happiness (or unhappiness). Don’t give anyone that power.

    Everyone has setbacks in life, it’s how you deal with them that determines your future. If you let a few mishaps make you give up on finding the love you want and deserve, you are giving up on your future. Not all dates are fun and enchanting, although my experience is only about 10% have been less than enjoyable. The great majority are unremarkable — not great, but not horrible. A few are heavenly, some resulting in equally sublime second and subsequent dates.

    After an unpleasant experience, journal about the lesson(s) from it, take a bath, get a massage, go out with a gal pal, have a good cry, enjoy a little chocolate, go for a rigorous workout, attend a comedy club, update your perfect boyfriend’s job description — whatever it is you enjoy. Decide how long you will wait to get back on the dating horse. Maybe it’s a few days, a week, or a month or two. But don’t wait too long. Or the horse wins.

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  • The choice: Break up or spend the weekend together

    My friend shared his dilemma and his choice. A woman he’d seen a few times wanted to drive 2.5 hours from her home to see him. While he thought she had many wonderful characteristics, he knew they were not a long-term match. He said, “I knew I had to break up with her then on the phone or let her come see me. I didn’t have the energy to deal with the crying and upset of a breakup, so I let her come spend the weekend.”

    “But you’re leading her on,” I responded. However, I know I did the same thing once. “You wouldn’t like to be led on. Now she thinks you’re more of an item.”

    “You’re right. But I just couldn’t deal with the aftermath of breaking up with her. So now that she’s back home, I’ve got to do it.”

    “And she’ll be even more confused and hurt.” I was trying not to chastise him, but instead help him see what he was doing to her.

    This was not a case of him being unclear on his feelings for her so wanted to give it one last chance. No, he was clear he was going to break up, he just wanted the timing to be convenient — for him.

    Yes, breaking up often causes at the least some tears and candid conversation. At the worst, there is yelling, name calling, arguing, perhaps dish throwing. I took the coward’s way out once — not returning a phone call from a suitor gone sour, then emailing him. I’m not proud of this, as I prefer to act with courage and integrity and have at least a phone conversation to share my thoughts.

    But I thought it was important for my readers to know that just because a man spends the weekend with you, it isn’t necessarily an indication that he is deepening his relationship with you. Some men will do it for the companionship, the physical closeness, the sex. Some will do it because it is easier than dealing with breaking up. While I won’t say women don’t do the same things for the same reasons, hopefully you wouldn’t. Know that this is how some men operate.

    Is my friend a cad, a player, a jerk? No. Although I find this behavior caddish. He is typically a caring, considerate, fun, intelligent, accomplished man. However, he — like most of us — can make short-term choices that are easier on him, without thinking through the ramifications for the other person.

    I remind myself and encourage you to act with compassion and integrity. If you know you need to break up, do so, even though you know there will be some cost of time and emotion. And, if you have been with the person more than a few hours, have the courage to do so ideally in person, but at the minimum on the phone. You will be happier with yourself in the long run.

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  • Managing disappointments

    Dating can take an emotional toll. You get your hopes up when it seems someone is a great match. Even when you try to manage them, expectations creep in. You start having hopes, perhaps fantasizing about a future together.

    Then something happens that dashes it all. A deal breaker emerges. A total impasse. Something one of you is not willing to live with. And it’s over.

    After spending 3 fun days together, nearly 24/7, he left with a promise to call that evening. He didn’t. I felt something was amiss. Giving him the benefit of a doubt that he was too tired or forgot to call, the next morning I emailed him a nice note, saying I had a wonderful time and looking forward to our talking. No response. A the end of the day, I called and left a voice mail asking him to call me back. Nothing. The next day I received a “have a nice life” email.

    We won’t go into how cowardly it is to send a blow-off email after 2.5 weeks of nightly hours-long calls getting to know each other and 3 days together. There is sadness, hurt and anger when you thought there was a possibility for a long-term romance that is shattered perfunctorily, without the honor of a conversation.

    How does one manage disappointments?

    It would be easy to blame and name call. I try to feel the hurt and sadness and let it be, rather than shrugging it off. If I bury the emotion now, it will come out inappropriately later. Allowing myself to feel the anger and pain helps me move through it more quickly than trying to bury it. A good cry is often therapeutic. But be careful not to linger too long in sadness or you can get depressed.

    After moving through the emotion, I remind myself that the person I am meant to be with wouldn’t treat me this way. I look for the lessons from the encounter and vow to apply them to future interactions. I focus on the knowledge thatpuzzle pieces what I learn from each guy is helping me complete the puzzle toward a great relationship. The most recent guy is but one puzzle piece toward the greater whole of a loving, trusting, growing relationship. The keystone piece — my match — has yet to appear. Some puzzles are simple, with only a few dozen pieces. Others have thousands. Let’s hope mine is less than 100 — as I’m on to man #72!

    How do you manage your disappointments?

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  • “There must be a pony in here”

    “Success is going from failure to failure without loss of enthusiasm.” Winston Churchill 

    People who know my dating philosophy and/or read this blog sometimes ask how I can stay so upbeat in the face of so many encounters that haven’t panned out. I admit that while to some it can sound exciting to have gone out with 71 men in 2 years, it has also been time consuming and frustrating.

    IllusionsOne phrase that keeps me going is from Richard Bach’s book Illusions: The Adventures of a Reluctant Messiah. You may remember Bach from Jonathan Livingston Seagull. Both were packed with thought-provoking philosophy wrapped around an engaging story.

    In Illusions, Bach says, “There is no such thing as a problem without a gift for you in it’s hands. You seek these problems because you need their gifts.” When you look at the problem as bearing a gift, you search for it.

    When I have a less-than-grand encounter with a date, I’ve learned to look for the gift. I know there is a needed lesson if I am willing to search. I ask myself some questions:

    • Why is what he did (or didn’t do) bothersome to me? What do I make it mean? Do I make it mean something about me?

    For example, if he kisses me passionately in public, do I interpret that as his not having respect for me? Thinking I’m a trollop? Why do I care as long as I know I’m not easy?

    • What is another way to interpret his behavior?

    With the passionate kiss, he could have felt such overwhelming affection for me that his desire to kiss me won out over any sense of inappropriateness. I could feel flattered that he is so attracted to me that he couldn’t wait to express it. Isn’t that part of romance — feeling so full of passion you want to express your love everywhere?

    • Did his behavior trigger a hurt from a previous time in my life?

    If so, I’m not upset with the current man, but from a past encounter that hasn’t been healed. Maybe someone from the past kissed me passionately in public. That experience coupled with other behaviors left me feeling disrespected. If the current man hasn’t shown other signs of disrespect, I shouldn’t burden him with the same hurt feelings that belong to the past guy. This trigger gives me an opportunity to explore the past hurt and heal it.

    • What signals am I sending that say this behavior is okay?

    I am playful, flirty, affectionate and accepting, so am I encouraging him to show public displays of affection and he doesn’t yet know what is beyond my comfort level? Did I tell him it isn’t comfortable for me and he persists?

    • What do I do that is irritating to him, yet don’t know it yet?

    If I put on lipstick at the dinner table (which I don’t, BTW) and it drives him batty, how would I know unless he mentioned it? And how do I want to be told so I can offer feedback to him in a similar way, at least until I know how he wants to receive such feedback?

    • Is he being a mirror for my similar behaviors?

    For example, I don’t like it when people interrupt me. But occasionally I find myself interrupting others. So is he unwittingly reminding me why people might not be able to wait to express their thoughts?

    Whenever someone does something I find annoying, I ask myself if I do the same thing or something similar. Sometimes I find I do, so their behavior reminds me to rein in my own.

    ponySo just like the joke about the child who enters a room full of manure and exclaims, “There must be a pony in here somewhere!” you can look for the hidden gifts in any encounter. The key is to believe there is a gift and to be willing to look for it, even if it means something not so great about you.

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  • Love me tender

    ElvisIn Elvis‘ song, he says,

    “Love me tender,
    love me sweet,
    never let me go.”

    Doesn’t that say a lot? Love me tenderly and sweetly. And when you do, I don’t want you ever to let me go. I want that tenderness and sweetness to last forever.

    The dictionary defines tender as “showing gentleness and concern or sympathy; loving kindness, kindheartedness, compassion, care, benevolence.”

    We want someone to love us tenderly, who will treat us with care and kindness. We want to be spoken to and treated with thoughtfulness and concern, with some appreciation for how the words might land in our ears. That’s not to say we aren’t willing to hear things we don’t want to hear. While some prefer truth without a cushion, I and other women want honesty wrapped in a soft down comforter. We still want the truth, but we want it given to us softly, with care, concern and compassion.

    This posting was prompted by a recent experience of my not feeling treated tenderly by a date — my third with him. When I did something he didn’t like, instead of telling me gently, it would come out brusquely. When I brought up something he didn’t want to talk about, he said, “Don’t go there,” instead of “I’d rather we not discuss that right now.” It was not only the pointed words, but the tone that made his comment feel harsh.

    For example, reviewing the menu in a fish restaurant, he asked what sounded good to me. I listed several fish choices, then noticed a favorite dish. “And the smoked chicken risotto sounds good too.”

    “We’re in a fish restaurant. You should have fish,” was his response. I felt like a child being reprimanded by dad. Shouldn’t I be allowed to have whatever I wanted without a “should” attached or my choice being questioned? Of course.

    When he groped me in public, I said I was uncomfortable and requested he not do it again. While I knew he was trying to be playful, it felt disrespectful. Instead of listening or apologizing, he said, “No one saw. And if they did, what do I care what they think? And you shouldn’t care what they think.” Thus negating my feelings. He showed he didn’t care how I thought or felt.

    Other comments accumulated that were small affronts. Nothing major, so I thought I wouldn’t make a big deal about them. We were just getting to know each other, so why continually nitpick minor infractions? While he showed tenderness in other ways, I was feeling less and less cared for. I don’t want to feel verbal pinpricks throughout an evening.

    I’m sure if I told him I didn’t feel he was being tender he would be incredulous. He was tender in his focus on me, physically with the exception of the incident above, and his general conversation. He had no idea how his comments were coming across, as when I did say something, he got defensive. In his 20-year marriage and subsequent relationships had no one given him this feedback? I’d guess no. Based on his descriptions of his past, I don’t think those women were any more astute about this than he.

    What do you think about tenderness? Is that a requirement in your romantic relationship? Are you as sensitive to this as I am, or do you have thicker skin?

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  • “I want to court you”

    hand holdingThese words are heart melting to a woman who wants love, romance, and a long-term relationship. No other man had said these to me. They were voiced after two weeks of nightly talking for hours about things that were important to each of us. What broke up past relationships, what was important to each of us, what we were looking for in a mate, what made us happy and unhappy.

    I was ready to be courted so was delighted when he said it. I interpreted it as he was romantic, wanted to make me happy, and had long-term intentions.

    How do you know if you are ready to be courted? He seemed to have so much of what I was looking for. He was funny, smart, accomplished, asked questions no one else seemed to care about, was interested in getting to know the real me. I was ready to fall in love. After many hours of talking on the phone, we seemed so compatible. I was ready to focus on one person, having grown weary of dating around.

    Did he court me? Yes. Coming from a 5-hour drive away, we agreed he’d visit my city for a few days. He reserved a hotel room and we met for dinner the first night. We hit it off immediately. We both thought the other was more attractive than the pictures in our profiles. We held hands and cuddled while enjoying a cocktail. We couldn’t take our eyes off each other at dinner. We later strolled to another nice bar and lingered over a night cap, not wanting to let each other go. We felt we’d known each other a long time. He said he hadn’t felt like this in a long, long time. Was this the love I’d been waiting for?

    His courtship had begun in earnest. He was doing and saying all the right things.

    The next day we enjoyed each other’s company with lots of laughter, deep conversation and cuddling. The following day evolved deliciously with late-morning coffee, exploring art galleries, enjoying the sunset’s flaming sky, and dining at a restaurant we discovered was a favorite for both of us. He was good at spoiling me and having fun.

    Did his wooing work? Yes and no. Generally, he was a good date, making sure I had what I needed to make me happy. However, while he was doing all of the above, there were also behavioral gnats gnawing at my patience. Was I being an ingrate for all the time and money he invested in showing me a good time? Was I being too sensitive? Too picky? No one is perfect. Could I live with these minor irritations? I know I have my own set of peculiarities that he would have to adapt to.

    We spent a lot of time together over 3 days. When you do, the annoyances mount up. With in-town suitors, you have lunch or dinner together, or spend an afternoon or day in an activity. Then you are apart for a day or more. It gives you a chance to give each other some grace and space. But by spending so much time together in just a few days, the irritants compound.

    Will his courtship continue? That is yet to be determined. We both need to decide if the things we enjoy about each other outweigh the burrs. Was there enough positive to invest more time on the phone and in person and see if we can work out the irritations? We will give each other some time to reflect and see what transpires.

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  • Your Date-A-Base — tracking multiple suitors

    When people hear that I’ve dated 71 men in 2 years and that I often date several guys simultaneously, they commonly ask, “How do you keep them straight?”

    I respond, “With a Date-A-Base.”

    Since I’m a business woman, I’ve long kept a database to track my customers. In business it is also known as a Customer Relationship Manager (CRM). I’ve adapted my business one to my dating life.

    In my Date-A-Base, I keep track of the man’s name, email, phone numbers, address, and picture. I copy his online profile into the electronic file. And I update it after we talk and I learn important things. This prevents me from asking again where he grew up, his family details, kids’ names and ages, alma mater, favorite hobbies, food, books, movies, etc. I review my notes before we I know we’ll be talking again.

    I start a database file as soon as we get away from email to the phone. I enter as much info as I have at the moment and add to it.

    When you have several people you’re contacting, it takes some organization to keep them all straight. Some people use a spread sheet to track their potential dates before meeting. My friend George, also a businessman/salesman, even had a pre-date spread sheet to track info on each woman with whom he was communicating. His was similar to how he’d track his prospects and customers. He’d log where she lived, if she was divorced or separated, how many kids and their ages, who initiated contact and when, and when they’d talked by phone. He’d enter her screen name, height and age, general looks (based on her picture) and “overall plus/minus” comments.

    Other people say they use index cards to keep people’s details straight. Others just print out the profile and make needed notes on it. I’m a tech-savvy gal so prefer the electronic version.

    Some of my dating friends have taken this tracking spread sheet to the next level. They have a number of categories across the top (looks, energy, intelligence, humor, etc.) and their dates’ name down the side. They then assign a number from 1-10 for each of the characteristics for that person. It seems cold, doesn’t it? But we all do that to some degree or another, just not so methodically. Then they can analytically decide if they want to continue seeing the person. I trust my gut more than my head, so this method wouldn’t work for me.

    The important point is do something to keep everyone sorted out. It’s embarrassing to say, “Will you be seeing your parents for the holidays?” when his parents are deceased. Or, “I hope Stanford whops CAL” when he’s a Berkeley alumnus.

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  • The deliciousness of pillow talk

    choc on pillowThere’s something delicious about late-night calls with your sweetheart. They are even more yummy than a mint on your pillow, and I love chocolate!

    When snuggled in bed talking on the phone the conversation seems to get deeper, more tender, and of course, sometimes provocative! This virtual tucking in can bring you closer as long as one of you doesn’t drift off. It seems easier to talk about hopes, dreams, fears and feelings than conversations in the light of day.

    Of course, I think the best time to discuss these things is when you are nestled in each others’ arms. But absent the other’s presence, you can envelope yourself in your sweetie’s voice and words. You can really focus on what’s being said without visual and tactile distractions.

    This connectedness can help you drift to slumberland feeling warm and loved. You’ll likely have sweet dreams, a restful night and wake up refreshed — assuming you didn’t talk til the wee hours! And when next you see your love, you’ll feel closer.

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  • Do you have time to wait to open your heart?

    A friend of mine died this week. I don’t know if I’ll ever become accustomed to people dying, especially when someone succumbs unexpectedly, as he did.

    When someone passes it prompts us to reflect on what’s important. Loved ones always appear at the top of that list. We become more appreciative of the gifts around us: a friend’s call, a sunny day, fresh-baked cookies, a child’s laughter, a warm hug, a beautiful sunset, a full moon rising.

    It also helps us put things in perspective. For example, this week I struggle whether to surrender to a strong attraction and let myself fall into intimacy. One pal’s advice: “Wait to go there. All good things take time.”

    But what if there is no time? Who knows when something will happen to any of us? Shouldn’t life be embraced fully and savored? Are you an eat-dessert-first kind of gal or wait-and-enjoy-it-in-time? I am a bit of both, but find myself becoming more of the former.

    Yesterday, Christine wrote a comment that I was “fearless.” Often when people point out what they perceive as my courage, I don’t see it as such. (See “Courage and Dating.”) I’m merely acting from the question, “What are my options?” I have the option to date or not. While I can entertain myself or with pals, there’s nothing like the embrace and kiss of someone who enchants you. I’m not willing to live without that for long. So I get “dated up” and have coffee dates with men who seem interesting and intelligent. Most end up just as coffee dates, but some become more.

    oudn heeledJane Juska’s book A Round-Heeled Woman: My Late-Life Adventures in Sex and Romance helped shift my perspective. (She put an ad in The NY Review of Books which read “Before I turn 67 — next March — I would like to have a lot of sex with a man I like.”) In her book she describes how she wanted to experience the pleasure a man’s caress and seduction before she got too old to enjoy it. It made me see that I’d made arbitrary rules based on my fears and doubts, not on living life passionately.

    Are there rules you’ve made about dating that need reassessing? Perhaps the rule was made after a painful experience and has limited your living fully because of fear of being hurt. Life and love are full of hurts. Hopefully, the pleasures far outweigh them. You can’t prevent all hurts by rules. But rules can prevent your embracing life. If you’ve closed your heart how can anyone get close enough to love you?

    Imagine you only had a year or two to live. How would you live and love differently? Would you allow yourself to be open to loving fully?

    A few years ago my friend remarried in his late fifties to a wonderful woman who adored him. He enjoyed her devotion and love for him and she shined in his. Now he is gone. If he had not opened his heart and allowed himself to love and be loved, he would have died without experiencing this midlife passion.

    Take off any shackles that hold you back. If you need some therapy to let go of your fears, call a professional now. You never know how long you have.

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