Dating In My Forties

Click here to listen to this article.

By the time you read this, I will be nearing my fiftieth year on this planet though most mistake me for an old thirty-five or a young thirty-eight. When making conversation with strangers in public places such as gas stations, grocery stores, and parks, I’m struck when people either my age or younger occasionally address me as “young man.” I make no effort to correct them. Instead, I appreciate that life has been kind to my appearance, everything considered. I have two children — a twenty-six-year-old son and a fifteen-year-old daughter who is wise beyond her years, as most teenage girls are. On paper, I have joint custody of the youngest with their mother. But honestly, it’s often hard to think of myself as anything other than a single father. I’m the only adult in my house. When my life as Dad challenges and stretches me, no one is there to guide me with that needed woman’s touch — to let me know I’ve said too little or too much or am applying too much pressure or not enough. Of course, my ex-wife is only a phone call away, but in these moments, there is no teammate present to step in to catch my fumble, run the ball for me when I’m headed straight into interference, or tell me to take a seat so she can do her thing. At least, that is what I believe should happen in the moments when I’m out of ideas and patience.

When Marriage Ends

I’ve been divorced for six years. I’m an ex-husband because sometimes marriage doesn’t work. Speaking only for myself, I didn’t know myself well enough to take on the lifelong ebbs and flows of getting to know someone else under the banner of “love.” Our marriage was a toxic mix of great times, mutual unmet and uncommunicated expectations, and unresolved, horrible arguments that went on for almost eight years. It was a continuation of nearly seven years of the same as boyfriend and girlfriend. It was this frighteningly perfect balance of good and bad that had us locked in a codependent two-step for nearly the entirety of our time together. Some family and friends on both sides had us doomed from the start. Others along the way couldn’t see how we would ever last. The rest hoped for the best — for our kids and us. To the uninitiated on the outside looking in, we were absurd. But for those who have spent time inside the picture frame of matrimony, we all know there are no black and white exit strategies when long-baked emotions, time spent, and children, especially, exist. Everything is shades of gray, up for interpretation and excusing, depending on the day or season. Unless one or both are willing to rip the bandage off.

My ex-wife was the one who did the ripping. I did everything my strength, hubris, and finances would allow to stop the bleeding, to save us, but to no avail. And after being exclusively involved with one woman for fifteen years, in the summer of 2015, I found myself single against my will. I was forty-three years old and terrified. My heart constantly raced at the thought of spending my days alone. In the beginning, all my nights were sleepless except for when I drank myself unconscious. Before being the father of a girl became a hashtag, raising mine was one of the purest joys of my life. Not being able to tuck my daughter in at night, every night, as I had since we brought her home from the hospital, was a punishment I wouldn’t wish on the one or two people I hate. I never cheated. I was never not home when I needed to be. If anything, I was guilty of caring and doing so much I didn’t notice we were growing apart. Back then, I was a captive of the amorphous concepts of right and wrong. I wouldn’t ever have thought she would leave until she did. My disbelief wasn’t born of some arrogant, baseless notion that led me to believe she was incapable of doing such a thing, but that she wouldn’t ever be willing. I learned otherwise and quickly discovered she didn’t share my reasons nor my desire. We were two different people. I wasn’t approaching the precipice of my forties. I had already taken the plunge. I didn’t see myself as only a parent. I wasn’t basing what the rest of my life might look like based on the present. I wasn’t in pursuit of happiness at the expense of comfort and, dare I state, the feelings of others. I feared the unknown. At the time, I wasn’t as brave as she was. I wasn’t nearly as strong.

Why she wouldn’t try to save us was and remains her cross to bear, but I made it mine for way longer than necessary. Bullied by my faith and my dogma of what was “the right thing,” I wholly embraced the notion that unreciprocated love had the power to fix all things. There are select times during a lifetime when challenges arise, and people step up to the occasion to be of aid to or even rescue others from peril. However, generally, it isn’t the responsibility of any adult to be the manager of the choices of others nor the consequences of those choices. I’d repeat this if it wasn’t grammatically incorrect. First responders, doctors, and your occasional, everyday citizen I referenced a few sentences ago are the only ones charged with saving others. In my effort to keep my family, I sought to save my wife from herself. Armed with my “good” intentions, I paved a smooth and sure road to Hell. Hell being a divorce I didn’t want and one she wanted even more with every effort I made to stop her. We began as friends and lovers. We ended as enemies and villains. Were resentment and contempt energies that could be seen as well as felt, I imagine our mutual disregard for one another burned so brightly it was visible from space.

Starting Over After Divorce

Until the summer of 2015, I had a set routine as a Black husband and family man. I was forty-three years old. I made six figures and had a brood that looked like those Target and Old Navy ads featuring those non-threatening, smiling Black families where the mother and daughter have curly hair and father and son have perfect smiles. I didn’t know how to be or who to be. My identity as a father and a husband was all that I had become, and it was abruptly and unceremoniously ended like a firing on a Friday afternoon. I was twenty-eight when I met my ex-wife in the year 2000. She wrote her number down on a ripped sheet of paper with a stubby pencil. I called her the next day from the landline in my Queens, New York apartment. We had our first date six days later and proceeded to paint the streets of NYC with experiences and memories for years to come.

At twenty-eight, women ten years younger than me were non-existent because they were girls. Of course, women older than me did, but as a younger man, it was common to believe these women’s interests in more youthful men were taboo curiosities or acts of revenge against a male partner their age who had wronged them. At forty-three, there were single women in their twenties, thirties, forties, and beyond. All of them were savvier than me. By 2015, most people couldn’t even tell you what a landline was. Smartphones were ruling the world. And in so doing they made landlines, pagers, flip phones, and face-to-face communication obsolete.

Dating apps and social media DMs quickly took over as the gateway drug that stood to be the cure for loneliness, broken hearts, or just wanting a good old-fashioned, no-strings-attached sexual encounter. For me, digital dating was the simplest, most low-effort way to “get back out there.” There was no need for fashion or the savvy one needs when sitting across a table from a stranger at a restaurant. But I quickly discovered that navigating this evolving digital terrain was akin to tap dancing in a minefield. For starters, I don’t know how to tap dance. Second, tap isn’t salsa. Salsa dancers become the music and take turns leading and following. I was out there tap dancing with a whole bunch of other people who either didn’t know how to tap dance or knew all too well how to, keeping time with themselves, trying to avoid all the other landmines when we were all out there being landmines. As far as I know, tap dancers don’t get lost in one another’s eyes. I’m sure plenty of tap dancers have fallen in love while practicing their craft, but I can’t say I’ve ever heard of someone randomly going out to tap dance and falling in love. But enough about tap dancing.

The Loneliness & Ugliness of Shame

In the beginning, my dating was a study in crashing and burning. No matter if it was online dating, the storied chance meeting of a lover at a coffee shop, or getting hooked up by a friend. In some ways, I was different from many of my brothers of the fraternity of newly divorced men. Regardless of how sad and lonely I was, I didn’t seek to escape my pain in the company of one woman or many. I had been with one woman for so long I couldn’t see anyone else but her. I didn’t want to. One time during those first, new months of “freedom”, I began to cry when a woman, while comforting me, pressed her lips against mine. Her lips weren’t my wife’s lips. The way she touched me wasn’t the way my wife used to touch me. It wasn’t the embrace I grew to anticipate even though I hadn’t been touched at all during the last years of my marriage. I was in a dangerous place, quite possibly the most dangerous: I was stuck, clinging to and memorializing a past that was not nearly as magnificent as I was making it out to be.

I wore the physical neglect of my ex-wife and my inability to change it like a proverbial scarlet letter that everyone who encountered me could feel, if not see. My shame left me feeling ugly and invisible. I accommodated and further strengthened these feelings by making myself small everywhere I went.

The Question, The Sharks & Well-Meaning Advice That Hurts

Once a man reveals his relationship status as divorced, the first question most ask is, “Why did you two break up?” It’s a simple question that typically yields all a woman needs to know once answered. I was no different but for reasons other than the obvious. I gave too many details. Shared too much pain and bemoaned too little objectivity. I was too in love with my past and my ex-wife. A whole woman who was comfortable and confident in her skin knew better not to hitch her wagon to mine. In the wake of their exit, they left behind three types of women:

  • Sharks who thirsted on the availability of a vulnerable man.
  • Pet lovers who felt it their duty to help broken-winged birds fly, and
  • Souls just as broken and lost as I, who thought they would be safer in the company of a miserable man than one who brought misery.

In essence, they were all sharks. The results with each were emotional bloodbaths, figuratively.

The best that friends could offer for my pain was ephemeral: “things will get better” and “God will get you through.” But there was no such thing as better. I could barely get through the day save for the fact that time didn’t stop ticking. And God had abandoned me. At the opposite end of awful things said to me there was “Keep trying, Bro. Women out here would kill to be with a good dude like you!” and “Let these females out here put it on you…you’ll get your swagger back in no time and then watch what happens.” But I didn’t want to. All I wanted was my past life. I wanted full access to my baby girl. I wanted out of the unfurnished, one-bedroom apartment I moved into from my fully furnished, four-bedroom townhome where I was husband and father. And I made this known to anyone listening, willingly and unwillingly.

Time Doesn’t Heal All Wounds, You Do

At the core of who I was, as in since childhood, I desired to be better. This desire fuels my love for fictional superheroes to this day. I refused to run away from my pain because something was telling me this experience could make me better — a better man, a better father, a better partner, should the opportunity ever come my way again, and a better judge of character. At the very least, a better judge of my character. To have sense enough to know which situations were good for me and which were not, refusing to be romanticized by “what feels good” now at the expense of later. Doing the work to become better required that I come face to face with who I was.

Time and Reality had their way with me the way trainers do with initially incapable but willing clients. Time was slow, too slow in my opinion, forcing me to be still in its patient embrace. From her, I learned the power of stillness no matter what storm may be brewing around me. Reality was a brutal taskmaster that stripped away the value of what had guided me most of my life: the thoughts and opinions of others along with the fabricated notion of what I “should” be. Reality slapped me hard with the inescapable truth about me: I was a man who aggressively pursued the acceptance of others. It was my drug. The high of acceptance brought with it the constant burden of pursuing it. I was a certified people-pleaser with hardly an individual desire that didn’t have at its core the need to satisfy someone else. The truth set me free. Then it made me angry.

You see, the providence of my divorce was that it was the key that unlocked the truths of who I had been, not only in my marriage but as a person walking this planet. The truths that come with self-discovery are as valuable as a goblet containing the elixir of eternal life or a cave filled with gold. But I didn’t revel in my discovery. Instead, I burned with anger against my parents and everyone else who participated in my origin story for doing whatever they did to contribute to my being a willing puppet for others. I eventually released my anger for them, recognizing they had done the best they could with what they had and did so out of love for me. With no one else to blame, my anger found a new, almost limitless source of fuel in my reflection in the mirror. I plunged headfirst into a months-long abyss of regret. I was a terrible date during this time.

Being angry all the time over a long-dead past was exhausting, and eventually, this too ran its course. In its absence, there was nothing. For the first time since meeting the woman who would eventually become my ex-wife, I felt lonely. This real loneliness was so overwhelming that it caused me to realize that these emotions, first sorrow, then anger, had been the ones keeping me company for who knows how long. It made sense that my attempts at dating were short-lived. There was no available space in my heart for a woman to try to occupy. Instead of becoming angry that I had been angry, peace settled over me, and I smiled. I closed my eyes, took in a deep breath, and finally forgave myself. Right then and there the rest of my life had just begun.

The House That Self-Love Builds

This new peace that I owned created new rooms in my heart. Empathy quickly moved in, occupying the largest one, and provided me with the ability to consider, if not wholly understand, other points of view and experiences. Dating stopped being what’s-in-it-for-me transactions between myself and the women I met and became learning experiences that taught me predominantly about myself. Even when the outcomes were less than favorable and, in some cases, downright explosive. Every woman I meet isn’t a good fit for me and the same certainly holds true for them. Sometimes it’s mutual. I learned from my marriage that what isn’t for me — isn’t for me. I was better off knowing this and not trying to convince myself otherwise. Seeing that Empathy was beginning to thrive inside me, Gratitude soon followed suit and got the next available room. Gratitude helped me lick my wounds and move on. Optimism began crashing on the couch and taught me not to lament the past and all its shortcomings. It graciously instructed me to look forward to who and what was next because, ultimately, each previous experience was preparation for the next. This practice of optimism would become my strategy for playing the long game — chess, not checkers. Patience was the final resident who moved in as my live-in chef, feeding me the strength and stamina required to play that long game. I was now officially a participant in my life. Despite all my initial resistance to not having things my way, God and the universe decided to bless me with the ability to choose how to respond to circumstances rather than react to them.

My heart, free from long-term anger and now filled with Forgiveness, Empathy, Gratitude, Optimism, and Patience, caused others to take notice. I was reflecting the light inside me. My warmth became warmth to others. My patience was giving friends, family, and everyone else refuge. My self-awareness and raw vulnerability brought with them a breath of fresh air to those who knew me and those who began the process of getting to know me. All my relationships across the board improved, and so did my dating. I was free of the weight of success or failure, the future, or any other societal or cultural expectation that comes with courting someone. Now light on my feet, with a pep in my step, spending time with someone for the chance to experience good energy and good times became the vibe, not landing dead-center on love or making more babies before the made-up deadline we all secretly give ourselves. I no longer desired to prove to an unconcerned world that I could succeed in love after failing in marriage my first time trying.

Mind you, the scars of my divorce and other past traumas are still there. I miss the job of husband and having someone to do life with. I miss the sound of constant activity in my home. My children wear scars, as does my ex-wife. But as time wears on and you continue to do the work on yourself, you begin to pay less and less attention. The bumps, bruises, and scratches you collect along the way become less noticeable until finally you wake up one day and forget that they are there because you are operating because of them, not despite them. I have a skin graft on my right hand from a third-degree burn I suffered in 1996, one year after grad school, and one year into the real world. I talk with my hands. Occasionally, I’ll notice the eyes of the person I’m speaking with follow the surgical work that covers the back of my right hand. Some are bold enough to ask what happened then want to know if I’m okay with something that occurred when I was twenty-five years old. Some go even further to empathize with how bad it must’ve hurt, or mention all burn victims they know. I let them know the pain was exactly what one would expect from a grease fire. It’s unimaginable. But it doesn’t hurt anymore, and my hand wouldn’t work without the graft. I don’t have a burned hand. I have a hand that still works after being deep-fried. I’m not a scarred person, I’m a person with a big scar on my hand. My scars, visible and not so visible, are not a subtraction from the original. They are additions that allow me to function better than I ever could have without them. In my opinion, the only thing that should be blemish-free is a paint job.

How did I go from a complaining, blubbering emotional mess to a person who enjoys dating and doesn’t mind the pitfalls that come with it? One day at a time is both the short and the long answer. I realized I owed it to myself first to know who I am, good, bad, and indifferent, and then decided to embark on a love affair with that person. Coming to love me through every stage and phase of my post-divorce life opened my eyes to a world of beauty I never knew existed before my pain. Learning to love me has taught me what love is and what it is not. Loving myself has made absurd the notion of sticking around to see if someone will meet me where I am when they are demonstrating they cannot or will not. This current version of me wouldn’t knowingly spend a second not being as good as possible to myself. Why settle for less from anyone outside of me? If I had it to do all over again, of course, I would do things differently. My human brain wouldn’t even consider repeating the mistakes I’ve made in its attempt to protect me at all costs. But if such an ability were possible, I can guarantee I would have neither the strength nor the experience to write these words.

Dating to Win

I’m a man who enjoys a woman’s company — company includes her touch, the different energy she brings to situations, and her perspectives. I do the work on myself every day to ensure I provide value from my side of the table. As I’ve stated throughout this piece, I do this by being good to myself first. These days, I date to experience life with and through others and maybe discover on the journey if I am compatible with someone else to create a season of memories — whether short or long. Should this change, I’ll be right there to experience and embrace the shift.

An older friend who often doubles as a mentor once told me dating is a numbers game — you only learn and succeed through experience. I used to bristle at the idea, believing too much was at stake, most notably experiences and time. But I no longer disagree with him. Dating in my forties, soon to be my fifties, has shown me that no experience is a wasted one. There are lessons even in the messes. All of it is a gift.

Take the Fear and Anxiety out of “Starting Over”

For moment-to-moment and day-to-day insights on how to turn power to pain and tragedy in romance or whatever it may be into personal triumph feel free to tag along on my journey on The Dating After Divorce Survival Guide, a serial podcast that thoughtfully and hilariously chronicles my journey as I navigate the challenges of “starting over” on multiple fronts after divorce. I created The Dating After Divorce Survival Guide to provide a path to emotional well-being that I never received and to tell the truth — men are just as scared as women (maybe more) when it comes to rejection and failing at love. But like me, if you’re willing to dig deep, work hard on yourself, and not play the blame game you can turn divorce into a springboard to discover yourself, discover joy, and maybe find love again or maybe for the first time.



Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store
Eric Payne

Eric Payne

Retired dad blogger and published author. Current host of The Dating After Divorce Survival Guide. All-day long Dad | IG: ericlpayne