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smarter dating at mid life, dating for boomersAs far back as I can remember I’ve been drawn to men who didn’t want me. Perhaps you can relate. My very first crush in 7th grade was on a guy who didn’t even know I existed. He was the star of the high school basketball team. I’d get all sweaty and blush if he looked my way or smiled at me. We didn’t talk or date until 9th grade! And even though we ended up together for 5 years, I was never quite sure if he really loved me. That was part of the allure – the excitement of not knowing, and the feeling of how special it was to get the guy who played hard to get.

But that was then. I was only a teen. I was figuring out how to date. What about dating in our fifties and beyond? I’m a little embarrassed to admit that when I began dating after my divorce, I’d still be attracted to the witty, good-looking man who never called back after a first date. I’d beat myself up and ruminate over our date. What did I do wrong that pushed him away? Turns out, the main thing I was doing wrong was chasing after men who didn’t want me. And I needed to break that pattern.

Toxic dating patterns are hard to break

I didn’t have enough confidence to break that pattern yet. I still didn’t believe enough in my self-worth when it came to men. My toxic dating pattern was all about the chase, wanting men who didn’t want me. I eventually did the inner work, and learned to love and value myself enough to stop this cycle of insanity.

I thought I was done with those hard to get guys. I was ready for a healthy relationship with a good man who wanted me. That’s what we all want, right? But sometimes our old patterns still need a little more work. And along came Bob (not his real name).

We were set up by a good friend. We met for dinner at an Italian restaurant. He was tall and handsome, just like my friend had promised. We discovered that we shared many common values and interests. He was smart, engaging, and sexy. We both loved the same inspirational TED talks. We enjoyed exercising in nature – he runs, I power walk. We had many friends in common.

We laughed and shared some fun stories about our children. After the date, he drove me to my car and gave me a warm hug. We both agreed that it was great meeting each other. I was positive he’d ask me out again. Cue the crickets. Nothing. Nada.

Why did he disappear?

I began to play the date over and over in my head. Why didn’t he call? Was it because I spoke about how bitchy teenage daughters can be? Maybe I shouldn’t have said bitch. Or maybe my outfit was too conservative, not sexy enough? Perhaps I wasn’t clear that I’d like to see him again. I said I had a good time, but I didn’t say, “I’d like to do this again sometime.” Yes, that must be it. Maybe he didn’t know I liked him!

I thought about him for about a week, and then I got busy going on dates with men who were more attentive – men who pursued me. I was having fun, but I wasn’t meeting anyone special. Every so often, I’d think about Bob again. He did seem to have so much promise. Oh well. I eventually stopped thinking about him.

Recently, I saw a good friend I hadn’t spoken to in ages. As we were catching up, I suddenly remembered that she knows Bob from her synagogue. When I told her I had gone out with him, she gave me a funny look. “Okay, why are you giving me that look?” I asked.

“Well…he’s not a good guy. He cheated on his wife many times with much younger women. His ex-wife is amazing. And she put up with his cheating. Finally, he asked for a divorce.”

“A cheater? Wow, I wouldn’t have guessed that from the way he behaved on our date. He seemed like such a good guy.”

“Yep, a cheater. And now he dates women half his age. He’s just looking for arm candy.”

Yes, I dodged a bullet

And there you have it. While I was wondering what I might have done to turn Bob off, it turns out he was a jerk. I am thrilled that we never went out again. I certainly dodged a bullet. It wasn’t me, it was him. Proof once again to stop wasting time on men who play hard to get.

Yes, I’m a dating coach and intellectually, I understand the key components of a healthy relationship. I can recognize a man who is emotionally available, a guy with solid integrity, someone who would make a fantastic life partner. I help thousands of women make better choices in the men they date. And yet, I am human. Sometimes it’s hardest to have clear perspective on yourself. I have had to work hard to increase my own self-worth and trust my dating intuition. It takes continued inner work to break old dating patterns and develop a healthy dating brain, balancing your head and your heart.

Find a partner who values you

Today, I no longer think twice about the man who doesn’t call back. If a man doesn’t call you back after a seemingly fantastic first date, you’ve probably dodged a bullet, too. Move on to find someone who values you for who you are. What I’ve discovered is that a girl will chase a man who doesn’t want her. A grownup woman will find a man of true character who doesn’t play games. Isn’t that what you want?

Have you ever chased someone who didn’t want you or played hard to get? Please share your story below.


For a copy of Sandy’s FREE report, “The Top Three Mistakes Midlife Daters Make (and how to turn them around to find love now)” please click here.

‘Like’ Sandy’s  Facebook page for inspiring posts on dating and relationships & links to her weekly radio show.


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