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Are You Smart, Successful, But Still Single?!

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We hate spam as much as you do!

“I’m 57. Booty calls are a dime a dozen, but a relationship worth having is rare at my age.”  This comment came from one of Facebook followers.

Yes, when you’re smart, successful and dating in your 50s  you face a unique dating pool. I’ve worked with some women who are Fab & Fifty who have never been married and others who are re-entering the dating scene after a divorce or death of a spouse.

What they’ve encountered are men who still haven’t matured (yes, age isn’t an indication a man has grown up yet!) or who are wanting to date around because they were married for most of their lives and now want to just “be friends” and “enjoy one another’s company.” Some have emotional and financial baggage and are trying to recover from a divorce or a lifetime of poor financial choices.

When they do meet a man who wants a wife, these men are often looking for a younger woman or they act like old men who are so set in their traditional ways and just want someone to cook, clean, and play nurse when they get sick.

Some of them really are sick, like the man Essie was seeing. “He said with all of his health issues, he wasn’t sure he wanted to involve me in that. But he’s happy to have my company.” 

But it is possible to meet a partner in your 50s! Let me share tips from the work I’ve done with a client named Essie (not her real name)

1. Reinvent yourself

Using my Making Room For The One System, we took a look at why Essie kept settling for emotionally unavailable men who just wanted to go to dinners and cuddle on the couch, but never commit.

We discovered that she was comfortable in these scenarios because she was happy being alone. A little too happy, in fact. Her contentment wasn’t just because she was comfortable in the skin she was in; it was actually a survival mechanism—The Strong Black Woman Syndrome— which helped her survive a loveless marriage. In fact, when she asked her friends if they knew of a great gentleman to introduce her to, one man replied, “I didn’t know you wanted someone. You looked really happy being on your own!”

In her marriage, Essie learned how to retreat inward and keep her family afloat by doing things on her own, until she decided she couldn’t live with her husband’s indiscretions any longer and got a divorce. We also discovered that this pattern of silencing her voice started with her relationship to her father who controlled most aspects of her life, even into adulthood.

The pattern of giving away her power extended into other areas of her life, including her church. There they preached a message that forbade anyone from marrying outside the denomination and so Essie felt like her choices were limited. When I showed her that dating an emotionally unavailable man and going to a legalistic church was rooted in the fact that she’d felt comfortable living with people who defined her life for her and that at 59, she didn’t have to live that way anymore, the lightbulb turned on.

Essie realized she was still relating to herself as the young woman who felt like she didn’t have a voice or a choice in defining her life. But she wasn’t that woman anymore, and she need to see herself through new eyes!

She needed to emancipate herself from her past. And she also needed to get clear on whether or not she wanted to get married right away, or if she wanted to experience dating different types of men and then choosing someone who would be a great partner for her life.

Essie’s reinvention included joining a new church, walking away from her relationship avoidant boyfriend and getting a makeover with an image consultant who helped her update her wardrobe and choose the right colors and clothes that accentuated her body (instead of covering it up the way she used to!). She also got a photo shoot for her online dating photos so that she could attract more quality men by showing herself in a new light.

2. Revise your dating list

Essie also needed to revise her “ideal partner” list so that the items reflected who she was a woman today, and not the woman she was when she got married over 30 years ago. I wanted her to focus more on the feelings she wanted to experience in a relationship, and less on the surface details like what a man looked like.

I wasn’t expecting her to date someone who looked like he was Methuselah’s cousin, but I wanted her to get clear on what it would feel like to open her heart to someone who was emotionally available. What was top on her list was a man who had a zest for life! She didn’t want to just sit on a couch and hold hands. She wanted to live!

3. Re-position yourself

With newfound clarity on who she was and the kind of life she wanted to live, we needed to position Essie in the right dating pools to attract the right partner.  Online dating was her best bet, but I also taught her how to ask people in her network to introduce her to single baby boomers. We discovered that Essie needed to rotate on different dating sites so that she could fresh prospects. Since she still wasn’t completely sure about when she wanted to be married, we decided it would be good for Essie to use casual dating strategically. She’d get to know different kinds of men before settling down, and she wouldn’t allow herself to be trapped in a situation with someone who was relationship resistant.

The final thing you should know about dating in your 50s is that you’ll need to be patient and enjoy the process. With the right perspective, dating can be a process that helps you rediscover and reinvent yourself. Be willing to change dating sites and meet a variety of men. Don’t waste time, however, with someone who isn’t going to be a good fit for your life.

Are you dating in your 50s? Tell me your challenges below!