02/24/2013 08:04 am ET Updated Apr 26, 2013

A Women's Guide To Smart Dating In Midlife

I was sitting at an Upper West Side café the other day, when a conversation at the next table caught my attention.

"I just don't get it," the perky brunette said to her friend. "We had so much fun together. We laughed and talked about our dreams -- he seemed to be really into me. I could feel it. Friends would even comment on how great we were together. So why in the hell did he suddenly stop calling?"

"Oh, he was probably just intimidated,'' her friend said, in an attempt to make her bewildered comrade feel better. "Or, maybe he was just starting to fall in love and got scared, or -- do you think he may have met someone else?"

Gee-whiz. Of all the conversations you prepare yourself to have in midlife, rationalizing the behavior of a new man probably isn't one of them.

As I sat there listening to these two very attractive, apparently accomplished, 50-something women have a conversation more befitting a pair of 20-somethings, I thought, no wonder so many midlife women are scared to death of getting back out there and starting over!

Just how do you get back in the dating game, when you've been out of it for way too long?

Maybe online dating is something to consider. USA TODAY reported people 50+ are one of the fastest growing segments among's more than 33 million users worldwide. The same goes for, where 25 percent of its members are between 50 and 65, that segment having grown 89 percent in the last five years (71 percent after a divorce and 11 percent who were widowed). That represents millions of singles looking for love. So, relax. You're in good company.

If online dating isn't your cup of tea, you can meet someone through professional contacts. You may ask friends to set you up, you could join special-interest groups -- book clubs, hiking groups, tennis teams, ski clubs or even a ballroom dancing or salsa group -- or you could just get creative. I once knew a newly divorced woman who wanted to meet available men, so she started a business offering cooking classes for divorced/newly-single men. Brilliant!

A great start is to just smile and say: "Hello!"

However you connect with a man -- the uncertainty, the angst, and the ups and downs of getting to know someone new all over again can be overwhelming and downright frightening. That is unless you put dating in perspective and see it for what it is: not just a chance to meet new people, but as an opportunity to reconnect with your authentic self and put your positive energy in play as you paint your clean white canvas!

Before you go out in search of that perfect date, be mindful of a few key points. For starters:

1. Center yourself, and get clear on what you want.

I'm talking about your deal breakers and must haves. What's most important to you and what are you willing/not willing to compromise on? Take a real, hard look within. How did you show up in your last relationship? How did your partner show up? What do you want to be different? Stay true to what you want and need, and go from there.

Getting clear about what you want will help guide your mind in all kinds of positive directions to help you find and attract the right situations and people in your life. Accepting a situation that is anything other than what you truly want will surely create unhappiness, and keep you tied to a man who's not right for you. Sound familiar? Truth: you must believe you are worthy of love, and that you deserve to be cherished. Be graceful, and don't sell out. It takes being smart and true to you.

Really ask yourself what kind of relationship you want before you become involved with a man and that fierce chemical attraction begins to cloud your vision.

2. Communicate with clarity and grace.

It's key to know what you want and to let a man know it. Actually, it's a must. Create that subtle balance between being outspoken about what you want and allow the unique connection to evolve.

Men crave honest women who are up front about what they want in relationships. It tells him that she's not too attached to the immediate outcome and subtly lets him know, if his behavior doesn't change, he won't have the pleasure of her company. This doesn't mean to announce on the first few dates that you're sick of the dating scene and want to settle down in the house with the white picket fence. It's not about ultimatums or threats. It's a clear statement about your wishes that also respects his right to choose.

When faced with open communication like that, a mature man will respect a woman and realize that he's dealing with an equal. This will ignite a deep level of emotional attraction, once you become vulnerable and state your truth, your respect for yourself will also increase, and with it your self-esteem.

You'll not only move closer to the relationship you want, but you'll weed out the guys who can't give you what you need.

3. Create space.

Once you connect with a man, even in an intense closeness, he may withdraw. Remember the woman in the café I mentioned earlier? What should you do if you're in a similar situation? Gracefully take a step back, allow yourself to be vulnerable and let him come to you. If you let go of the need to control what happens next, and give him the chance to call and make plans with you, or initiate affection, this will create the space he needs to recover emotionally from the intensity. Sound counterintuitive? Perhaps, but this is often what happens.

And if he doesn't regroup, this man may not be living on his essential purpose and does not have his overall well-being in check, or it may just not be the right time for him, hence why he becomes restless and withdrawn, preventing him from showing up for you. In this case, he's not is a good place, and your needs are not being met. Face forward and move on.

4. Enjoy the experience.

When you're in the midst of or freshly out of a Big Life Change, the very idea of allowing yourself to enjoy any experience can sound and feel ridiculous. You might feel guilty, or ashamed or undeserving. Ask yourself how those feelings might be serving you?

The bottom line in relationships is this: Trust that people do the best they can. Accepting whatever that "best" is, and how that matches with your needs and what's true for you, is where the rubber meets the road. If someone isn't capable of showing up to fit your needs, then all you can do is accept that fact, have compassion for them and set yourself free. Don't try to convince him, over share your feelings, set unrealistic expectations, or have "the talk." Keep it simple. Stay true to yourself and good things will come. It's a far more enjoyable way to live life, and it works. You'll be surprised! Now, get out there, and let me know how it goes!

P.S. Remember: men find happy women attractive. You just have to adjust your lens and be willing to stay open and while you create a healthy, optimistic outlook on life.

Are you a smart, bravehearted midlife woman who is a phoenix in the making? If you're an open-hearted, classy lady devoted to making forward momentum after a Big Life Change, or if you're just needing to rekindle your midlife spark, click here to receive upcoming registration details for The Society for Zestful Living, a supportive and illuminating group coaching experience for women ready to create their New Normal.

Nancy Sherr coaches bravehearted women through Big. Life. Change. A coach, writer and speaker, she is the creator of the Society for Zestful Living group program for women. Visit here to get Nancy's free five-part eCourse: Fierce Grace for Bravehearts: a Practical Crash Course in Navigating Change.

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