Dating As A 40-Something Single Mom

Sometimes finding love means getting rid of all your unrealistic rules and guidelines.

Dating is on my mind. I turn 41 next month. My marriage ended three years ago. My divorce is near final. I still believe in love. Of course, I am not certain of the everlasting type or how love manifests for a single working mother of two.

Eighteen months ago I decided I was ready to open up to the possibility of dating, at least just for fun.

Initially, I pursued the “respite” date—the type of date that allowed me to escape from my children and all the overwhelming responsibility of sole parenting. Respite dating had nothing to do with the children, and the dynamic with a respite man was temporary with no real investment in long-term compatibility. Some singles seek it in the form of casual and frequent sex. Others look for a friendship with benefits.

As a self-proclaimed serial monogamist, I looked for a committed respite—a productive love defined by friendship, emotional generosity, great conversation, and wonderful physical intimacy.

Thankfully, I found it with surprising ease. I met a respite man who became my lover and more importantly, a dear friend. We enjoyed time spent languishing over a bottle of wine, a cup of great coffee, and a good meal. We committed to the respite and the friendship—nothing more.

Despite the casual path I had intended to walk, I eventually opened up to the notion of a progressive love. While we had designed friendship into our relationship, we had not created space for the possibility of permanency. In the year we spent together, I turned the corner in my heart’s healing and began to change the script of dating for myself. I desired something more connected to my life with my children, my family, and my friends. Eventually my lovely respite man ceased to offer a real respite.

I’ve since shifted my dating strategy to focus on the “progression” date—the date that offered the possibility of a real commitment to a long-term partnership. Progression dating involved my children. I crafted a different dating lens, one that involved my whole family. My maternal lens became integral to the natural sorting and sifting process inherent to dating. Three years after I left my husband hollow of heart, I caught a glimpse of my own hope reawakening. I began to explore a vision for my life, albeit cautiously, that involved a productive, collaborative, integrated love.

Careful to preserve my heart and protect my children and our home, I asked myself in 1,000 different ways:

  • What do I want in a partner this time around?
  • What do I need? What do my children need? What do our lives need?
  • What are past patterns and desires I need to shake off to find the right fit?
  • How must our life stages match up?
  • How much does he earn? What type of career does he have and aspire to develop? How does it align or conflict with my own ambitions?
  • How will I introduce a man I date to my children? When?
  • What are the deal breakers?
  • How will we merge households? Could he love my children as much as his own, and I his?

Despite my openness to a progressive love, I wore a heavy armor of wariness. I came out blazing—all cards on the table, unfiltered honesty. To my horror, I found myself asking a man before we even went out on date, “Divorced, no kids? Are you a breeder? I have no interest in having children.” I was clear, perhaps, uncomfortably candid about my needs, desires, parameters, and objectives, and brutally honest about my flaws. I promised myself that the next man I would love would not be the one to woo me. And, I made absolutely certain no man had the chance to do any type of wooing.

I entered the singles scene with some ridiculously strict guidelines:

  • Divorced with kids. (I assumed any man in his 40s without kids would eventually want to breed.)
  • Over the age of 45. (I assumed with age came safety, confidence, and financial maturity.)
  • Definitely NOT writers, actors, artists, or musicians no matter how successful. (With two children to raise, I didn’t have the patience for the never-ending creative process. I love the intersection of art and commerce, but pure art…no way.)
  • Earn at least equal to me. (I certainly did not want or need someone’s money. I just wanted to be sure he was steady, focused, and driven. For some reason, salary seemed a good indicator.)

Not surprising, I learned with each date that my guidelines were entirely misinformed, arrogant, and full of fear and misgivings about that hope for a new kind of love I had glimpsed.

As I eliminated each guideline, I discovered something very real for me. I now love in a “we” formation that includes my babies. While that makes for a more expansive, inclusive, productive kind of love than I have ever shared with a man, I recognize that my new way of loving might also seem an immense burden for a man. At the outset, I would have to explain how I love so that he could determine for himself whether my way of loving was full of parameters or possibility.

Three months later, I am dating a man who is 43, divorced, without kids, and a writer. He is building a new life for himself with a vision of love steeped in a hope that is similar to that of my children and I.

I’ve replaced that all-consuming, blind, individualistic love of my pre-marital youth with an eyes-wide-open love that includes all that is thoughtful and generous about responsibility. It’s in this type of responsibility that I’ve finally found the real respite.

Katerina Zacharia is a media executive, teacher, and sole parent raising two children on her own. She is passionate about her work in media, diversity, and education, her children, her friendships and family, and keeping her sanity. She has no nanny.

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