EDITOR’S NOTE: CoverStory is launching “Two for the Road,” an advice column on life, love, and loss.

Cathy is in private practice as a grief, loss, and transitions coach.  She is an author of four books, two of them on grief.

Mark has been a registered nurse for 47 years and is an educator specializing in end-of-life care. He was director for training at the second largest hospice in North Carolina in the United States. 

I am a 52-year-old single parent. My marriage was annulled three years ago. I have two sons who are both in college. They have been encouraging me to go out and date again. 

I really do not feel the need to do so because I am happy with my life and my career. I plan to retire when I reach 55. I have a couple of old friends from high school who are both widowers now. They have been sending feelers about going out, but I am hesitant to open myself up to love again. 

I am a 52-year-old single parent….What should I do? – On the fence

CATHY: The 50s is an interesting time in a woman’s life. If the 40s were filled with angst, the 50s are a quieter period marked by many moments of reflection and clarity. I heard that the 60s (I’m not quite there yet) is an even more peaceful time filled with adventures because one is hopefully still strong enough, and braver to pursue and fulfill the unfulfilled dreams. That, in a nutshell, is how the next 15-20 years of your life will look like.

It sounds to me that you are happy and fulfilled in different areas of your life. You are also, it seems, about to become an empty nester. The sons, most likely, have their own world and set of friends; once they go into the work world, marry and start their own families, it will be a different season of life for you. 

I understand how you can be on the fence about dating. I really don’t know much about your history and why your first marriage ended, but I sense that there is still some hurt from that episode in your life. You also mentioned that you hope to retire in three years. My guess is that you are financially independent as well. 

Perhaps it will be best to use the next three years to heal yourself well and get to know yourself better. Healing takes time, after all. I imagine you were in your previous marriage for close to 20 years. When you eventually decide to enter another relationship, you must be sure that much of your wounds have healed, and that you have left most, if not all, of the baggage from your first marriage.

I’m glad that your sons are open to the idea of your dating again. My guess is that they only want you to find happiness with someone when you enter your senior years. It’s good to have male friends, and not of the romantic sort if you are not yet certain that this is what you want. From the onset, you must be clear about this so as not to give false hope. 

Part of preparing for a new relationship is knowing what you want. What are your non-negotiables? Make a list of ten traits. The top five are the non-negotiable ones. Don’t settle for anything less. You’ve come this far, and it sounds to me like you are a woman who knows your worth. 

Ask yourself: “What can this other person bring to the table that I cannot do for myself?” Learn well from the hurts of the past and take time to get to know this person with whom you are contemplating sharing your life. Nothing good comes easy. It’s good to begin as friends, to share many interests, and to know that your values are aligned. 

The senior years need to be devoid of drama or stress. Those are years that need to be filled with joy, peace, love, and, yes, adventure. Loving is always a risk. You need to ask yourself if your heart is strong enough to take this risk. Love, when you give it time to grow, is always a risk worth taking. 

MARK: Sounds like you are in a “good spot” in life right now with your career and feel “settled.”

It’s OK to be OK. Your sons obviously love and care about you and want only the best for their mom. Likely, they see that your empty nest is approaching as they finish up their schooling and begin to move on with their careers and starting families of their own. My guess is that they want to make sure you live your best life full of love and not just settle for OK. 

When I separated and divorced from my wife, each of my three children told me they wanted me to find someone I could love and be loved by. They wished happiness for me and knew that although I had a fulfilling career and great friends and family relationships, my personal need for intimacy was yet to be fulfilled. 

Some valuable advice a professional counselor gave me was: First, write down a specific list of what I want now; second, read and complete the exercises in the book, “Rebuilding: When Your Relationship Ends” by Bruce Fisher. 

Dr. Fisher outlines the 19 steps people go through after a breakup. Each chapter is short and features a brief questionnaire at the end that helped me work through what I needed to do to seek the best for myself and start a new loving, fulfilling and lasting relationship. 

It’s important that you also listen to your “gut” when dating again. Make sure the guys aren’t just needy and trying to fill an emotional hole. Verify that they’ve done “healing work” on themselves and have something to offer you from a full heart, not just a broken one. 

Starting over is scary. Knowing what you want, and don’t want in a life partner is critical before you put your toes back into the relationship waters. 

Settling for “OK” or less than the best for yourself may be a regret you will look back on when your sons have left the nest. 

Come on in … the water’s fine!
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