Why You’re Scared of Dating (and How to Dump that Fear)

I’ve been helping women over 40 find passionate, grownup love for 8 years. When these fabulous women come to me for support, most admit that they are scared of dating.  And most fall into three relationship categories:

  • Women who have never been married or had a relationship in which they felt loved.
  • Women who have been married, or had long term relationships, and never felt loved.
  • Women who were married, loved and in love, and are now widowed.

Would you be surprised to know the women who have been widowed after enjoying a good marriage find love (again) much quicker?

I was kinda astonished at this! Then I figured out exactly why.

These strong, magnificent women have been through a horrible experience, yet they have far less hesitation about putting themselves out there. They know the splendor of grownup love, want to experience it again, and are willing to learn and do what they need to if it means finding love again. They are much less content with staying in their safe, “my life is just fine” place.

I finally realized that the risks of getting out there and unapologetically looking for love, were far outweighed by the reward of being loved by a good man.

Here’s what I think: these amazing women know the reward of having a loving, devoted man in their life. They miss having a warm, rich, intimate partnership. They don’t want to live their lives without it.

You see, these women are not scared of dating, because they know the reward of having a partner in life.  The reward far outweighs any of the risks of dating to find him. 

That doesn’t mean they aren’t scared as crap to be “on the market” again. They are just as afraid of getting rejected, being hurt or possibly even not meeting another man to love. They are bummed that, at this stage in their life, they are single and have to put themselves out there. They have already been through a terrible emotional ordeal. There is definitely fear and worry.

Like my client “Lori,” who was one of the very special women in my 6-month Love Program – a highly successful and personalized private and group coaching program (which I will be offering again in the next few months).

Lori was in her fifties when her husband died, leaving her to raise her teenage son alone. As scared as she was to date again after 20 years, she just couldn’t imagine living the rest of her life without what she had with her husband. With him, she felt safe, loved and adored every single day. They were physically and emotionally bonded, and the very best of friends. He always had her back. And she his. They were a real team, facing life together.

Lori knew what the rewards of a good relationship felt like, because she experienced it for 20 years. She listened to me carefully about how to date like a grownup. (She hadn’t dated since she was quite young.) She learned to open herself up to men, and how to express who she was and what she needed to be happy. I taught her how grownup men are different than the boys she dated before she got married. She put herself online and dated several nice, but not-for-her, guys.

Then, Lori met “Steve” through friends. They have been together since their first date. Their lives are complicated since they both have children and Lori is very careful about bringing another man into her son’s life. But she is committed to trying to make it work with him. And yes, she is still a little scared.

In many ways Steve is a different guy than Lori’s husband. But the feelings she has for him, and the rewards of the relationship, are familiar. It’s what she had before, and what she didn’t want to live without. It’s exactly what she had the courage to Go For It. And it seems she’s found that spectacular love she was missing.

I was so damned scared of dating…so I’d quit

During my 30 years of dating I never experienced grownup love. I was pretty happy with my single life and, like the women I now coach, was really scared of dating. When dating got hard, and my fear of dating became stronger than my fear of dying alone, I would retreat and go on dating hiatus, and sing my ‘I don’t need no stinkin’ man’ mantra.

I had some periods of years between dates. I wasn’t touched. I wasn’t noticed or appreciated in any way by a man. But I thought that was worth it. I was better off without the confusion, rejection and potential broken heart. That just hurt too damn much. And it didn’t seem worth it to me. I thought I was being strong by staying single.

When I turned about 45, I felt so sick of being single! I knew I wanted a partner to spend the rest of my life with and I committed to do whatever was within my power to find him.Larry adoring Bobbi

So I did. I went into therapy (before life coaches were popular), learned about men, got help getting online, consciously and bravely worked on myself…and kept my eyes on the prize. I finally knew that I wanted to love and be loved. And I went after it.

Two years later, in 2006, I met and married my husband.

For all those single years, the risks of dating seemed far greater than the rewards. With all the insecurity, self-doubt and false beliefs that I had, it was easy to retreat into “my life is good enough” and give up on the idea of having love in my life.

I didn’t know what being loved by a man looked or felt like. Before Larry, I had never experienced the kind of love that made me feel safe, cared for and special. I didn’t know what it was like to be #1 to anyone. To have that man who works hard every day to make you happy.

With help, I finally allowed myself to imagine being loved like that. I started to believe it was real…and possible. I believed I (more than) deserved it. And the scales began to rebalance.

I finally realized that the risks of getting out there and unapologetically looking for love, were far outweighed by the reward of being loved by a good man.

Unlike Lori, I had to imagine it. But we came to the same conclusion.

I’m here now on the other side. The blush of early love is over. Larry and I have been married for 9+ years as I write this. We have been through a lot. We truly know each other, and we really like each other.

If you’re like I was, and having trouble imagining what grownup love (the reward) looks like, here are just some examples:

  • He loves me even though I can be super selfish and a pain in the ass.
  • He was there for me every second, and cried with me as we watched my dear father die.
  • He gets me chicken soup when I’m sick, pays our bills every month and stays up until midnight helping me do last minute work because I procrastinated all week.
  • He “gets” me and supports me in every way possible, even when he thinks what I’m doing is a little crazy.
  • When I see myself in his eyes, I like what I see.

I love being part of a couple – more than I even thought I would. I have a wonderful travel partner, a constant dinner date, a cute guy to snuggle with on the couch each evening and most of all, the security of knowing that this smart, fine man always has my back.

So, in retrospect, was this reward worth the risk I took of getting help, doing some things differently, and putting myself out there? Was it worth the hassle of putting together a profile, answering some emails, going on a bunch of dates, feeling broken hearted a couple times and dealing with a few jerks along the way? As my granddaughter would say, “Duh, ya think?”

Are you like I was? Do you sometimes feel overcome by the weight of the fear, confusion, and frustration of being single and dating? Well, I’m here to ask you…no, to tell you…that it’s time to get real about the risk vs. reward here. Is what you could have really not worth a few crappy moments along the way?

I want to hear from you! What are your thoughts on my risk vs. reward theory?? Leave me a comment below.


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