Four Simple Rules For Dating the Second Time Around

If you are re-entering the dating world. here are several rules to follow in order to avoid losers and leaches.

If you are re-entering the dating world. here are several rules to follow in order to avoid losers and leaches.

By Karen O’Sullivan

Many well-intentioned people have said to me over the years, “When the time is right, you’ll find the right guy. There’s someone out there for everyone.” Of course all of these do-gooders are married. What do they know? They aren’t living the nightmare of being over thirty and re-entering the dating world.

When I found myself suddenly single, many years had passed since I had been on a real date. Although I had been married, in no way did our relationship involve “dating.” The progression of our relationship was typical. Our courtship lasted for about a year, but dealing with a typical man, “dating” stopped after the first month, when he became sure that I was going to stick around. (Canceling my adventure to Australia, moving into his beach pad and the utterance of that fatal “L” word, must have been all he needed to turn the love-o-meter down and settle into complacency.)

So, we basically “dated” for a month, then cohabitated. Cohabitation, mind you, free of dating. Yes, we went out, but the excitement was gone. I didn’t wait by the phone for him to call. He just had to shout from the next room. I didn’t dress up to catch his eye and receive a compliment. I had already taken to wearing his clothes. I didn’t wait by the door; breathlessly anticipating the ring of the bell and a hand held walk to the car. Instead, we met at the car when we were both ready to go. No wondering whether I’d get a goodnight kiss, a follow up call, another date. No mystery. No magic. Dating was done.

Eventually we got married. Had kids. Settled into a ho-hum, life is over, now we are an old married couple routine. Now, not only was the romance abandoned, the mystery gone, we also never went out. Not even a “shout from the next room, throw on an old sweatshirt, I’ll meet you at the car in five minutes” night out. Nothing. Needless to say, the marriage did not last. Of course the end to dating was not the only reason we broke up, but it was a significant reason. Going out gives couples a much-needed break and a chance to reconnect. Every book I have read on the subject says, “Married couples need a date night out. Even if it seems contrived to have to schedule time together, DO IT! Every week.” We didn’t do it at all.

So, we got divorced. If you do the math, there was a year of a dateless relationship, three years of marriage, a year of separation, then divorce. That adds up to five years without a date. Understandably, the thought of joining the dating club again was terrifying. But, when one of the members of that endangered species called “single men” asked me out, I summoned up the courage to say “Yes” and began my long journey through “dating hell.”

Trying to find an eligible bachelor when you are over thirty is next to impossible. If you are re-entering the dating world after a long vacation, here are several rules to follow in order to avoid the losers and leaches I encountered and find Mr. Right.

Rule # 1: Make sure he is able to carry on a conversation. “That’s nice” and “Hmm…” don’t count.

My first encounter was a fix up. I was working in a restaurant where one of the customers apparently had spotted me and thought I was cute. He asked his friend to ask me if I would go out with him. Kind of junior high, don’t you think? After a brief conversation, he seemed to be somewhat normal, so I agreed to a dinner date. We met at a local restaurant. The food was good, the atmosphere enjoyable. The dinner conversation, boring. I had a lot more fun talking to myself. He had nothing to say, no stories to tell, no accomplishments to brag about and no future goals to share. Needless to say, I did not agree to another date. A couple of years later I found out this guy ended up in prison for money laundering. Good thing it didn’t go anywhere.

I endured another fix up with a guy I barely knew a few months later. Over our first drink, I knew it was going no where. Trying to carry on a conversation with this guy was not only difficult; it was painful. I think he had left his personality at home. I struggled for an hour, trying to keep the conversation going. I asked about his family. His response, “They’re nice.” I inquired about his job. “I like it.” Any future goals. “Not really.” I talked about myself. His longest response was “Hmmm.” Once we got to our table, I ordered quickly, ate quickly and got out of there quickly. No thank you to date number two.

Everyone knows that a conversation requires two people. Even if you are the most skilled conversationalist, a date won’t work if your companion has nothing to say. Communication is the key to a successful relationship. You might as well find out right at the start whether or not this will be a future problem.

Rule #2: Make sure he is unattached. That means wives and not so ex-girlfriends.

After going out with two dullards, I remained dateless for another year. Dating seemed like too much work to be worth the trouble of finding a baby sitter, dressing up and dealing with a nervous stomach. But, alas, as time passed, loneliness set in, so with much consternation, I agreed to another fix up. This time, a blind date. “What are you nuts?” you are probably saying. Well, yes. I knew that going on a blind date was just asking for trouble. It’s like looking for the prize at the bottom of a cracker jax box. You don’t know what you are going to get until you dig to the bottom of the box. If you don’t like your prize, no returns, you are stuck with it. I agreed to meet him at a party. I didn’t know what he looked like so I nervously scanned the crowd for what seemed like hours. Finally a man approached me. He was short but passably cute and definitely no slouch in the conversation department. I liked him instantly.

We ended up going on two more dates. Each time was more fun than the last, until the very last date. We were supposed to have dinner at my house. I should have known disaster was about to strike when he showed up an hour late with no warning phone call. He not only did not apologize; he didn’t even try to explain why he was late. He just grabbed a beer from the refrigerator and sat down at the table waiting to be served. I tried to make the best of it since I had spent hours preparing a romantic, gourmet meal. After dinner, he made his move. In his mind, date number three meant he was going to get lucky. I had no interest in moving our doomed relationship to that level and said so. I mistakenly used the “c” word. All I said was, “I will not do that until I decide to make a commitment to someone.” Harmless enough, I thought. He flipped out and shouted at me, “Commitment, I can’t give you a commitment! I’m still married!” I looked at him in shock and dismay as he ran screaming from my house, never to call again. It turned out that our mutual friend had forgotten to tell me that he was going through a very messy divorce and wasn’t quite ready to move on. After his dramatic exit, I never heard from his again. His loss, I decided.

My next attempt at dating was not much more successful. Another blind date. My good and trusted friend knew of my dating woes, so swore to me that her friend was not only single but also definitely a keeper. She was right. He ended up being tall, dark, handsome, successful, fun. The list could go on. For our first date, he picked out a wonderful place I had never been to. The conversation never lagged. We laughed. We smiled. We had a great time! He called the next day to set up date number two. We chatted on the phone a couple of times for hours at a stretch. It seemed too good to be true. It was.

Our second date was great. We went to the theater, had a late dinner, stopped at a trendy coffee shop. The date was flawless. The problem arose about a week later. After calling him a few times and receiving no response, I asked our mutual friend what was up. It turned out, his long, lost love had come back to him and they had gotten engaged. He had only started dating after their breakup to kill time, all the while plotting how to get her back. Guess that meant we were done.

Oh well, live and learn. I was at the age where I saw no need to date a guy if there was no chance of a serious commitment. I’d be much better off finding out about any dangling attachments before beginning a relationship. Remember that wives are not classified as “ex” until the ink on the divorce paper is dry. Ex-girlfriends are also a problem if your intended has plans to win her back. Stick with single guys. I mean really single. You’ll have a much higher success rate in the dating game.

Rule #3: Do not date younger guys. They aren’t grown up enough for a relationship.

Shortly after my blind dating fiasco, I met a nice guy. He was someone I knew by sight, but had never talked to. After an impromptu conversation one day on the beach, we decided to meet for dinner and ended up dating steadily for about two months. A record in my world of dating. Of course there was a problem. He was much younger than I was. Seven years. Depending on where you are in your life, age should not matter. But as a good friend of mine says, you should never get involved with men under the age of thirty because they have not grown up yet. They’ll have a relationship as long as the words “commitment” and “forever” are never, ever uttered. At the time, I had not yet met this friend so I was not privy to this information. I jumped in head first, totally blind to approaching disaster.

At first our relationship seemed to be going smoothly. We went out every week. We had fun. We truly enjoyed each other’s company. But, it didn’t last. Like most men, he simply disappeared. After our last date, he just stopped calling. I never saw him again. After careful analysis, I decided that the age difference is what killed it. He wanted to play and I wanted to be involved. Not necessarily with him, but with someone. That knowledge was too much for him to handle, so he cut and run.

I was not heartbroken. I had known all along that he was not “Mr. Right.” He was a lot closer to “Mr. Maybe”, probably even more deserving of the title, “Mr. Wrong.” Plus, a couple of weeks after his mysterious disappearance, I met another guy. He was another young one. Nine years difference this time. Although it may seen I was drawn to younger men, I was in no way a cradle robber. There simply were no eligible men in my age bracket. I was willing to take what I could get.

This relationship lasted for about a month. He lived in another state and only came down to his parents’ summer home in my neighborhood for an occasional weekend, so it was doomed to fail. The big clue that he was not really interested came when he never bothered to RSVP for my thirty-fifth birthday party. I called him to ask about it and ended getting the “I don’t want a commitment, I’m not ready for anything serious” speech. Whatever.

I had learned my lesson. Younger guys may be nice to look at, no wrinkles or gray hair, nice firm bodies. But, a firm body does not go far if you are looking for a commitment and he is sowing his wild oats. Although single men in their thirties are hard to come by, avoid younger men at all costs, unless of course, you are sowing your own wild oats. A firm body can be a pleasant distraction from your dating woes.

Rule #4: Beware of personal ads. There are many frogs among the princes.

I was sick of dating but even sicker of being lonely. I decided that I needed a new approach. I knew people who had placed personal ads but I had never considered this option. I thought only losers and rejects had to advertise for a date. I spent some time thinking about all of the losers and rejects I had dated over the past couple of years and decided that maybe I was going about it in the wrong way. Maybe all of the guys looking for commitment were placing ads. figured it was worth a try. I was very systematic in my perusal of the ads. I quickly learned to read in between the lines. “Likes quiet evenings at home” meant boring. “Mature” meant old. “Free spirit” meant fear of commitment. Fifty ads were narrowed down to ten, then ten to two.

The first ad I called was pretty straightforward. It described the man as 35, 6’4″, athletically built, likes kids. Nothing wrong there. Our first conversation went well. I learned that he was divorced, had two kids, and lived by the beach. We spoke several more times then agreed to meet in a local bar. He described himself as having a football build with a short black crew cut. I figured I couldn’t miss him. The bar was packed so I scanned the crowd carefully. I noticed a heavy, balding guy looking at me, but quickly dismissed him because he did not fit the description I had been given. I stood in the bar for about 15 minutes, feeling like a complete idiot, but no one approached me, so I left. I called his house to see if he was running late but ended up getting his machine. I explained what had happened and apologized for inadvertently standing him up. It turned out that the heavy, balding guy was him. He left a message for me later that night blasting me for blowing him off. He self-righteously proclaimed that he might have acknowledged my presence if I had bothered to walk all of the way up to the bar. But since I couldn’t be bothered to make the effort, either could he. Jerk.

“Never again,” I told myself. “I am happy being single. Loneliness isn’t that bad.” I tried to convince myself that dating was a shameless waste of my time. I did not want to try and fail ever again. But, I remembered what all of my married friends had told me about waiting it out for the right guy. decided that I would wait it out in the privacy and security of my home. If Mr. Right was going to find me, he was going to have to find me on my couch.

I sat at home for about two weeks. The second ad I had circled was still lying safely and innocently on my coffee table, just begging to be read. This ad was funny. My kind of humor. “Looking for a lover who won’t drive me crazy. Know that one? If not, move on, you’re too young.” What did I have to lose? I took a deep breath, dialed the phone, listened to his recording and left him a message to call me. After several conversations, I hesitantly agreed to meet him for a drink. I made it very clear to him that he had about 60 seconds to make his presence known. If I couldn’t spot him easily, he was done. No second chances.

My palms were sweating as I walked through the door to the bar. I didn’t want to meet up with another loser. The description I had been given was dark hair, leather jacket and jeans. Knowing that the majority of guys in the bar would fit that description, I figured I would never find him and the date would be a bust. Believe it or not, I spotted him immediately. Miraculously, he fit his description and he had pulled his stool out from the bar so he would stand out from the crowd. A quick drink to check each other out turned into five hours of intense conversation. He was wonderful! He was exciting! He was funny and successful and intelligent and cute! He was over thirty. He liked kids. We clicked immediately.

Many months later, he told me that as soon as he spotted me he fell in love. As he watched me walk toward him he was silently wishing, “Please be her, please let it be her!” For me it was not love at first sight, it took about fifteen minutes. After years of wading through the swamp of frogs and toads, persistence had paid off. I found Mr. Right.

I’ve decided that dating is like exercising. It’s painful. It’s boring. It makes you sweat. You really don’t want to do it but force yourself to. Like exercise, dating can have its’ rewards. If you stick to it and follow some simple rules, you just might end up with a healthy, strong relationship that other people admire. So my advice is, don’t become discouraged. Keep my rules in mind and someday, when you least expect it, Prince Charming will magically appear. You may even find him while reading the paper in the safety and security of your home. Remember, when the time is right, you’ll find the right guy. There is someone out there for everyone.

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