Reading: Learning to Love Again: 5 Tips for Dating in Midlife

“If I meet him offline and he looks nothing like his pics, he’s buying me drinks until he does,” I overheard a woman tell her friend as I sat eating my crab and asparagus salad at Via Quadronno, my favorite lunchtime eatery in Manhattan’s Upper East Side. As I quieted my smile, the woman continued, “Is it over for me? Will I spend the rest of my life alone? I should have left him when I was younger — before he left me.” I felt deep compassion for these two over-50 women sitting beside me, trying to get back into the new, complex world of love. I could hear the resignation in their voices. 

Our lives and the promise of living happily ever after are more complicated than ever, and for those of us in midlife, it can feel scary, unmanageable, and sometimes even profoundly disappointing. Most of us are struggling with current partners, ex-partners, a difficult divorce (or even divorces), grown children who leave home (then return home), aging parents, illnesses, unthinkable losses, and the huge amounts of adjustments we’ve had to make to survive them all. It can sometimes seem like the heartbreak list is endless. 

As a loss, trauma, and grief specialist — and a divorce recovery coach — I have been honored to watch from front-row center as my clients have navigated all these twists and turns. Returning to the world with openness and vulnerability is scary after heartache and disappointment have ravaged your reality. Still, there comes a time when you must choose: You either cut yourself off from life (resigned and hopeless), or you open yourself up to the courage it takes when you’re learning to love again.

Learning to Love Again, the Right Way
Finding love after 50 probably looks much different than the dreamy, youthful pictures in your head. In this stage, Prince Charming may show up on foot, as he lost his white steed in the settlement. The beautiful princess, meanwhile, may be wearing an estrogen patch. And that’s okay. The old partnership rules can be redefined, and love and commitment can deliver a new depth. Love in Act Two can be more beautiful than you ever imagined. Youthful passion often butts up against the practicalities of building a family, career, and a sense of security.

Dating in midlife can, for sure, bring some physical or even mental challenges. But it also brings the richness of authenticity that comes through hearts having been broken, things held dear having been lost, and strengths, understanding, and resilience having been redefined and honed over time. Somehow, thank goodness, this makes us more attractive to anyone we would want to build a life with — and equipped to love with an all-consuming passion and honesty we weren’t capable of when we were younger.

Those of us who are older and wiser can find context through connection rather than circumstances. This gives us a fantastic opportunity to love and be loved for what and who we truly are today, rather than for what or who we may become.

What are the Rules for Dating in Midlife?
So, what are the parameters for keeping yourself prudent, realistic, and enthusiastic while exploring love after 50? These are the top 5 guidelines I have developed in my nearly 30 years of coaching — and have used myself as a successful midlife dater and finder of true love after divorce:

1. Finish your unfinished business! We all have some painful history, but don’t unpack your baggage in someone else’s closet; that’s a recipe for failure. Don’t get stuck or enchanted with your drama, old stories, or yesterday’s wounds. Do the work it takes to complete them and heal. Discover where you need forgiveness and where you need to take responsibility or find closure. If you need help with this, get it. Don’t allow life’s disappointments to be an excuse not to fully commit to what you are creating with a potential partner now.
2. Find happiness on the inside. No other person or external circumstance can bring you lasting peace. Contrary to romantic lore, love needs a sense of reason, not romanticism, especially if you want it to last. Studies have shown that people who are happy with themselves, know who they are and what they want, and have a solid sense of autonomy have a greater chance of forming sustainable relationships. So, cultivate your own sense of self and inner peace. Gain an understanding of what your needs and desires are. Your joy lives in you, not them.
3. Understand the difference between chemistry and compatibility. Chemistry is about an energetic and emotional connection between two people and has more to do with dopamine receptors than true partnership potential. When researchers from Syracuse University conducted a study called “The Neuroimaging of Love,” they found that when people fall in love, several euphoria-inducing chemicals are released in the brain — triggering the same sensation of excitement and euphoria that people on cocaine experience. Can you rationally choose a life partner while on cocaine? True compatibility is when two people share a natural alignment in lifestyle, values, and spiritual beliefs. This is the foundation for a happy, and successful, long-term relationship.
4. Be flexible with your expectations. A full, joyful life in this new stage requires a new paradigm. Don’t let yourself be constrained by your old images of what love, relationships, or marriage should look like. Try on something new. Be patient, and remember, nobody is perfect, including you: If you’re going to have a checklist for them, you must create a list about yourself. In middle age, very few of us look great on paper! Give people a chance.
5. Grow from failure and disappointment. Life may have failed you a thousand times, but it has also likely gifted you many blessings. Aim to be even-handed in evaluating your past and present. The experience of loss is not optional in this lifetime, so you must acquire the tools and skills to heal and grow from it. Have the courage to love after loss — and when you do, love fully. If it ends, you won’t hurt less for having held something back. You’ll only wonder what would have happened if you had given it everything.

Learning to love again, especially in midlife, can be the most powerful, passionate love you’ve ever experienced. You have struggled in your life; you have survived situations that you never imagined for yourself when you were young. You have the depth, passion, wisdom, and commitment that only comes with challenges, time, and complexity.

There may be precautions to take when being fully open, but one of the truths of love is that while loving another is never truly safe, loving is the fullest expression of life.

So be bold and do the work to heal fully, and life will start to feel like a wild, wonderful ride rather than a scary and dangerous drop. And if they don’t look like their pics… have another martini!

Melanie is a PCC-level ICF-certified coach and an ICI master-level coach. She has been working and coaching in the fields of heartbreak, loss, trauma, grief, reinvention, and change for over two decades and has helped thousands of people globally create profound and lasting change in their lives. She recently published Unfinished Business: 8 Steps to Heal Your Trauma, Transcend Your Past, and Transform Your Life. You can connect with her on Instagram @melaniesmithofficial  or on Facebook