Adventures in Delicious Dating After 40™

Category: Are you ready for Mr. Great?

  • Dating is like house hunting

    “He who hesitates is a damned fool.” —Mae West

    My friend Ken Braly wrote a hilarious piece, “Finding A House, Finding A Spouse” (posted in the Pages section) about how dating is like shopping for a home. I see this parallel.

    If you are shopping for a new home, you would want to see properties that are close to what you’re looking for as soon as possible. You have some urgency because you know the property is on the market and many others are looking at the same place. If you don’t act quickly, you could miss out on your dream home.

    Sometimes I am surprised by the guys who start emailing and/or calling, but don’t seem to have any urgency about meeting. The only conclusion I can make is they aren’t that interested in me. Of course, they may already be dating someone and fishing to have a “reserve” woman in case the current one doesn’t work out.

    So by not setting something up, they may be missing out on their dream woman. I’m not meaning to sound conceited, as the knife cuts both ways. If I ignore the calls or emails of someone who seems promising, he may become disinterested, or meet someone who better fits his criteria.

    If a man seems too urgent — pressing to meet me the same day we connect — then he seems desperate. There has to be a balance.

    But if he’s made contact, we’ve emailed and chatted, and there’s no “close” for the date, I get the impression he’s not very interested. Even if he is traveling the next day, most guys who are interested will put something on their calendar for when they return.

    So don’t let your dream guy move on by not responding within a day or two of his contact. And if he doesn’t invite you to meet him within a week of your chatting and emailing, he probably isn’t that interested. Move on, as there are other properties to look at!

  • No rules for dating after 40

    I was sharing my dating life with a married friend. She said she was glad she wasn’t dating now because there are no rules. When she was dating (40 years ago) there were rules. “Like what?” I asked.

    “No kissing on the first date.” “Really?” I responded incredulously. “I’ve had some fantastic kisses on the first date. What else?”

    “No sleeping together on the first date.” OK, that one I agreed with. “Go on.”

    “Men are gentlemen and open doors, pay for the date, make sure you get home safely.” OK, those are fine.

    “But there really aren’t any rules,” I explained. “People come from different experiences, so you have to just be clear on what your rules are and don’t bend them.”

    Which can be hard. If you are really into each other, it would be easy to progress as if you’d known each other for a while. “It just feels so comfortable,” you tell yourself. However, that momentary comfortableness will lapse into hurt and betrayal if you allow yourself to go farther than your “rule” would allow, then he never calls again. You feel used, undisciplined, and perhaps slutty.

    So know your own rules and boundaries. And when you want to ignore them — or he is coaxing you to do so — know it’s time to end the date for today. I’m all for spontaneity, but know that sometimes spontaneous actions cause a lot of pain later.

  • Dr. Jekyll/Ms. Hyde: Start the date on the right foot

    Yesterday a male friend told me how his last date lasted 5 minutes. He’s an affable, considerate, tolerant guy, so I couldn’t imagine what could go wrong in 5 minutes.

    He said he’d had great, fun, pleasant, in-depth phone conversations with the woman, then asked her to a high-end restaurant for dinner. Nearly immediately after sitting down, she started telling him he was too religious and finding fault with other aspects of his life that are important to him. Even for this patient, sweet guy, enough was enough. He said “This isn’t working for me,” paid for the wine and left. He said he’d felt he had met Dr. Jekyll and Ms. Hyde.

    If she had trouble with his religiousness, she should not have accepted the date. Telling him was not going to change him. The only thing it changed was his willingness stick around and treat her to a nice evening.

    First dates are about getting to know each other, not about fault-finding. You should be your best self — being on your best behavior but being yourself as well. You shouldn’t pretend you are someone you aren’t, but you should work to make yourself appealing enough that he wants to see you again.

  • Long-distance suitor and the first date

    “Absence makes the heart grow fonder— of somebody else.” —Anonymous

    A man who lives 400 miles away has been flirting with me for months and calls every day. He decided he would fly to my city this weekend to meet me. He’d get a car and a hotel room, so there would be no discomfort with him wanting to stay with me.

    Today he called and said “I have an idea. Why don’t you come here? Some weeks ago I’d made plans with the guys to golf at a resort a few hours away, and I still have the reservations even though the outing is off. And it would be easier, as I wouldn’t have to schlep my golf clubs on the plane to your place.”

    A few things immediately crossed my mind. First, easier on who? Certainly not me, as I’d have to schlep myself (sans clubs) to his place, then be at his mercy unless I rented a car.

    Also, this was the first mention of golf. Isn’t the whole point of getting together to spend some quality time and see how we like each other? When he’s spending one day of the two we are to be together on the golf course, that limits our getting-to-know-you time.

    Then there’s staying at the resort. This is our first time meeting. Would he expect to sleep with me? Or do I rent another room? This first encounter was now starting to cost me a pretty penny for a guy who was willing and interested in me enough to come to me.

    I stammered that I would think about it and we could talk about it later today. I will bring up my concerns, especially about sleeping arrangements.

    First dates can be hard enough without adding the complications of feeling put out by the arrangements. If I were advising someone else, I’d say save the resort time for later in the relationship when you know you click. I think I’ll take my own advice!
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  • Hello — goodbye: How to say no thanks after meeting

    One of the hardest parts of dating is telling your date that it isn’t a match so you don’t encourage him to pursue you.

    It is easiest to do in an email, but I only recommend this method if you’ve only met once. Start with thanking him for coffee, lunch, whatever. Comment on some of his positive characteristics. Then tell him it’s not a match:

    “Thank you for treating for coffee and our interesting discussion. You certainly know a lot about politics.

    “You are an intelligent, warm, fun gentleman. However, I don’t feel we are a match. The right woman will snap you up soon!”

    Harder is on the phone. I’ve had to do this when a guy calls to set up a second date. It is uncomfortable, but you need to be gentle yet honest — up to a point. Recently, after the guy asked when he could see me again, I said “I appreciate your interest in me, but we’re not a match. You are a nice, fun guy, but I don’t feel we have enough in common to continue seeing each other. And it wouldn’t be fair to you to accept another date knowing that I don’t feel the spark I know needs to be there to develop a relationship.”

    He said he was disappointed, but he understood. He said “So I’ve gained a new friend.” “Exactly,” I replied.

    The hardest way to communicate your lack of interest is in person. I’ve not done this often, but it is definitely uncomfortable. The other day at the end of lunch, my date said, “So what happens next?” He wouldn’t have said this unless he was interested in a second date. “We need to decide if we both want to spend more time together,” I replied. “It’s up to the woman,” he said, “so what do you want to have happen next?” I squirmed. “Since you are new to online dating, I suggest you date some more women,” was the best I could muster. I just couldn’t be blunt and say “I don’t really want to go out again.” While many men appreciate honesty, they also have fragile egos.

    I followed up with a thank you email wishing him well in his dating adventures. That made it clear.

    You don’t need to go into a review of all the things he said or did that were a turn off: How he used his finger for a pusher on his plate rather than a knife, interrupted you a lot, rarely asked anything about you, picked up his lamb chops with his fingers to eat them, or showed up at the nice restaurant in sweats. No, most men don’t want to know that kind of detail. And what may have been annoying to you may not be to the next woman.

    Strive to be kind, gentle, and to allow him to keep his dignity. I always appreciate it when a guy does that to me.

  • Building your Franken-boyfriend

    I’ve fantasized about putting together my perfect man — my Franken-boyfriend. After dating a lot of men, I’ve grown very fond of different parts of many. I’d like to build my perfect man with the beautiful green eyes of one, the height of another, one’s sense of humor, another’s deep, resonant voice, the kindness and sensitivity of one, the dancing skills of another, one’s superior intelligence, the kisses of another, the attentiveness of one, the adventurousness of another, one’s business acumen, the caresses of another, one’s playfulness, another’s sense of style.

    If you were to put together your Franken-boyfriend, what characteristics would you pull from your male pals or fantasy dates? It’s important to identify what’s important to you, but to realize that outside the movies, one man who contains all those attributes probably doesn’t exist. So be clear on what is most important to you.

    One way to become clear is to notice what you like and don’t like about your dates. Keep a list of each. You’ll discover that something you thought you wanted gets on your nerves if overdone. I like whomever I’m dating to call and touch base each day. However, I realized there was a limit to this when I had one boyfriend call me 5-6 times a day to tell me what he was doing. I like affection, but one guy’s kissing me every 10 minutes was too much.

    So notice what you want in your Franken-boyfriend and be prepared that you may fall for someone who doesn’t have some characteristics you thought were very important!

  • Dating takes time

    I continue to be surprised when people don’t seem to understand that dating takes time. It takes hours to sort through potential matches, contact them, email and talk on the phone. Then there’s an hour to meet them, if just for coffee. Dinner is 2-3 hours. A hike or bike ride, movie, theater, concert, dancing, etc., is many hours. Yet some of the guys I’ve talked to seem to have already over-full schedules with work, kids, friends, hobbies, working out, etc. So when do they think they’ll have time to develop a relationship?

    I dated a guy for 6 weeks who rarely made time to see me during the week, even though he worked less than a mile from me. When I’d suggest he come over after work for a drink or dinner, he rarely accepted, saying he was too tired and just wanted to crash. Early on, he made it clear that Friday nights were boy’s night, and Sat. day he did his home chores and errands. Sunday he spent with his daughter and Sunday night he prepped for his work week. Which left Sat. night. Period.

    So how did he expect to develop a relationship in a few hours a week? He multitasked his phone calls during his commuting, so when he arrived at his destination the conversation ended. There was little consideration, I learned, for what I wanted. What if I wanted to see him during the week, go to a concert, movie, or just hang out? Too bad. We played by his rules or not at all.

    Be honest with yourself — how much time each week are you willing to devote to finding and developing a love interest? Do you think you can just float into a relationship at your whim? That might be fine for those who just want a casual relationship or a booty call, but for someone looking for something long-term, it rarely works.

    And if he isn’t willing to invest some time, notice that early on and move on.

  • Is that you? Pictures are just a rough facsimile of the real thing

    When I was first dating, I wouldn’t respond to someone if their picture wasn’t appealing, even if they sent an articulate, fun email. I also turned down any contact who I couldn’t imagine kissing, based on his picture. I didn’t meet a lot of new guys with these criteria!

    Now I’ve learned that pics in online dating profiles are an approximation of what the person looks like. Even recent photos don’t reflect the twinkle in his eye, how cute he is when he smiles, or how he makes you laugh with that silly expression. So I’ve learned to give him a benefit of a doubt if his profile, emails and calls are intriguing.

    The other rampant problem with photos is many folks (men and women, I’m told) post pictures more than two years old. I think it is dishonest to post any pics more than 2 years old, even if they are among recent ones, unless you put the date on them. I’ve only not recognized one guy when I met him because his pic was 10 years old. I was attracted to my first online date because of his picture with little kids. When I met him, I realized those were his kids, not the grandkids he’d mentioned to me. In other words, his picture was 30 years old!

    I have also met lots of guys who posted pics from when they were 60 lbs. lighter, or had hair (or hair another color but gray). I understand they think that if they present themselves as younger, they will get more responses. Perhaps they expect they will use their charm to overcome the disappointment of their date when she is having coffee with the white-haired guy with the paunch, not the buff stud in the pic (from 20 years ago). It’s seldom worked for me.

    So, the lessons for you: 1) only post or send pics fewer than 2 years old, and 2) if other things are compelling, go ahead and meet the guy even if his pic isn’t.

  • Faux beaus and practice dating

    When I first began dating, I was advised to go out with nearly anyone who asked, just to practice. Since I didn't want to take advantage of anyone, I kept these practice dates to coffee. These dates helped me shore up my confidence and hone my skills at talking with men I just met about relationships and other things that one doesn't usually bring up on first meetings.

    I'm not proud to admit it, but I even had a faux beau. This was a gentleman who treated me well, and liked my company, and mostly I liked his. But I knew it was not a long-term match. I called him my faux beau because he called me every day, we went out several times a week, and I was fond of him yet I knew we were not a match.

    When my conscience convinced me it was not fair to him to keep seeing him, as he would not find his true love while dating me, I let him know. He still wanted to see me, but I knew he wouldn't date anyone else if I acquiesced. I told him to date other people and we could do things together occasionally as friends, which we do now.

    So if you haven't dated a lot, consider practice dates, but be considerate. Plan for short-time, low-cost activities. Always be pleasant even though you know it isn't a match. And who knows, a practice date might turn into your soul mate!

  • Deciding to see him again or not

    Even when there isn’t the immediate physical attraction or chemistry, I’ll sometimes see a guy again to see if there is any underlying spark that needs a second chance to be kindled. If there was nothing odious on the first date, I may try once more.

    Last night is a good example. The gentleman arrived on time, wore nice, pressed casual clothes for our stroll to my local neighborhood dance party. He didn’t try to maul me with kisses and too-soon affection — in fact we only hugged hello and goodbye.

    However, during the stroll and dinner, he interrupted me a lot — something that is a pet peeve of mine. While he did seem interested in what I was saying, he also often tried to summarize what I said — but he was wrong each time. I know I am usually a clear speaker and when others summarize, they most often get it right. So it was clear he and I weren’t thinking along the same paths, and it got annoying after a while to keep correcting him.

    So the bottom line question for me is, “Do I want to spend more time with this guy?” Do I find him interesting — or appealing — enough to invest another hour? While I’m easy going, and can find interest in nearly anything, if there isn’t enough to keep me interested, best to let him go. I’m afraid that is my conclusion about last night’s date.

  • Courage and dating

    “Life shrinks or expands in proportion to one’s courage.” —Anais Nin

    Last night in a class I’m taking, I briefly shared my story about how I’ve come to reenter the dating world, and how much I’ve learned from many of the men I’ve met. The instructor told me she was awed by the courage I have to keep at it even though I haven’t yet met Mr. Right. Afterward, a number of women told me how inspiring my story was, as they either hadn’t dated since they’ve found themselves single, or have dated but been frustrated so gave up.

    I don’t think of myself as a particularly courageous person, although I know I’ve done things that the majority of the population wouldn’t consider doing. However, I compare myself to mountain climbers, sky divers, race car drivers and others whose courage far outpaces mine.

    But the more I thought about it I had to agree that dating does take some courage. You make yourself vulnerable putting yourself out there, warts, double chins, extra pounds and all, and risk rejection. I have been rejected, sometimes painfully, but often when I’m not a match for someone my date either says so matter-of-factly, or, if he has no courage, he just disappears.

    The other options, however, aren’t very effective. You can go about your normal business and hope to run into Mr. Right, be introduced to him by friends, or be lonely staying at home by yourself. By putting yourself in the game you hone your flirting, dating, and communication skills (if you’re at all conscious), and you clarify what you want and don’t want.

    So if you haven’t yet dipped your toe in the dating water, I encourage you to start wading. The water may be a little bracing at first, but you’ll get used to it and you’ll find yourself swimming in men in no time!

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