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Dating at Midlife: What You Need to Know

There seems to be two types of people when it comes to dating in midlife: those who are the proverbial kid having fun while looking for the pony in the pile of …well you know what, and those who consider it a necessary evil to be avoided, sometimes at all costs.

I’d like to propose that there is actually a middle ground and that the thought process and actions reflected in this middle ground thinking will yield two critical outcomes: enjoyment during (most of ) the dating process and a higher probability of achieving the results you are looking for. The following are things you need to have in place to work from this middle ground:

1. Know thyself…and get a quick read of others

Did you know that you can tell a lot about a person if you know what section of the newspaper (for those of us who still read our papers rather than the online version) he or she picks up first? I should have known what I was in for when my soon-to-be husband consistently reached for two sections—sports and travel. That pretty well defines his passions. As for me, well I guess I’m what you might call a “closeted romantic”: people are always shocked to learn that the first section I reach for in Sunday’s NY Times is always and invariably the wedding and engagement announcement section. I look for interesting stories and guess what: they tend to be about people who marry in mid-life or later. There are a few important things I’ve learned from my very un-scientific survey:

* People are lovable (in the relationship/romantic sense) at any age.

* While the tendency is for men to look for women of a significantly younger vintage,
there are plenty of men who are looking for someone around their own age. In fact, there are a growing number (in my anecdotal study) of couples where the women are a few years older than her lover.

* With age comes clarity. As I read about what brought these couples together, it is almost always based on mutual interests and a deeply held sense of knowing “this is the one.”

So perhaps the first question you ask a potential date might be: what section of the paper do you read first?

2. Don’t put all of your eggs in one basket.

Recognize that dating is just one aspect of your life. Imagine for a moment that your life is made up of a portfolio of activities. Much like a financial portfolio, think about how you invest your time now; then reconsider how much time and energy you actually want to invest in each area of your life. As we age, we are more certain about who we are rather than former stages in life where the focus was on who we wanted to become. Take that heartfelt knowledge and look for another sage soul who shares your interests and passions. Look at relationships like a series of puzzle pieces making up the picture of your life—there are many different pieces in your puzzle—take some of the pressure off by reminding yourself that a romantic relationship is just one.

3. Be thoughtful about re-entry into the dating world.

The biggest challenge associated with getting back out there in the dating world typically has more to do with self-confidence than anything else. I like to encourage people to get into “game shape” for the dating experience. What are the things that are present when you feel and look your best? Need a new style? Take a visit to the make-up counter, hair stylist or boutique and treat yourself in a way that makes you feel good about how you present yourself. Are you getting enough sleep? Eating well? Exercising? Before entering the dating world it’s often really helpful to set some goals. In addition to looking better on the outside, you’ll be taking care of yourself on the inside too. Research has shown that those people who understand and pay attention to their physical, emotional, spiritual and cognitive needs feel more energetic and report higher levels of happiness and life satisfaction. Carpe Diem—the dating will follow!

4. Define a successful date.

We’ve all lived long enough to know that having expectations of how people will act towards us and how we “should be” tend to be an excellent predictor of disappointment. It’s no wonder many dates end on that note or something close to it. The secret to successful dating is to look at the entire experience with a light heart and to imagine that it is part of a grand experiment rather than a means to an end. Dates are simply potentials for connection. And we all want connection. What I don’t advise is to go to that first date with hopes like: “This might be the one: he sounds perfect on paper and my friends say we are perfect for one another—I hope I don’t screw this up!” What I do advise is to set your intention around finding the following three things out on your date:

* One thing you have in common (a hobby, past history, etc)
* One goofy thing about one another
* One thing you would like to learn more about him/her

A friend of mine recently tried this and reported back that it changed the whole dating experience for him — from anxiety producing to enjoyable. Rather than focusing on how the date “should” be (How should I be? How should she be? Is this going well?) he felt as though he had something to do. This scavenger hunt of information can even be shared with a date. It takes the pressure off. Try it and let me know how it goes. I’d love to hear from you.


About Barbara Waxman, MS/MPA:


Barbara Waxman, President and founder of The Odyssey Group, works with business owners, executives and individuals increase their leadership capacity and their ability to deliver concrete results. Barbara founded The Odyssey Group in 2005 in order to use her skills as an executive and life transition coach for adults, midlife and better. “My passion is working with people for whom the primary tasks of middle adulthood have been complete. Children may have (almost) been raised. Relationships have stayed the course, dissolved, or are on the horizon. Career goals have been achieved, have been a disappointment or are being dreamed of. The question we face is “What’s next?”