Chapter 30: Finding My Worth At the Border

What’s wrong with me? Why can’t I find someone special? What can I do to change? These are the burning questions on the mind of every single woman. The questions we regularly ask family and friends. The questions that plague me as I end my summer…still single.  

It strikes me that men don’t ask this question; it doesn’t even occur to them. The answer is simple, they say, “it’s my choice.” Their cavalier attitude toward this issue pisses me off…as I witness most of my incredible single female friends be tormented by this mystery.

These women are successful, productive, interesting… they mother, they volunteer, they have side-hustles, they have rewarding careers, they give to others, they are thoughtful. And the longer they stay single, the better they get at life, yet the harder it is for them to find a partner.

As the summer comes to close, and I look back on all the fantastic parties, trips, accomplishments, and the beautiful relationships I got to nurture…I wonder why I am still asking this question.

A couple of weeks ago, I was laid up sick for five days with a terrible fever and body aches. Possibly payback for working too hard, partying too much and never giving myself time to rest.

As I dragged myself to the doctor and laid on my couch, I had a lot of time to think.  My think time included a dose of self-pity and a pinch of self-abuse (thinking can bring out my inner saboteur). While it would have been easy to slip into the pit of despair and feeling sorry for myself instead, I chose to take a different approach.

The flashbacks of date after date, bad relationship after bad relationship played in my head. As that horror film played out, I had a moment similar to the moment in the movie when you yell at the girl who’s walking into the room with the murderer in it…STOP! RUN THE OTHER WAY!

I had an epiphany, there was nothing wrong with ME per se, but there was something wrong with the choices I’ve made. The question, I spent a lot of time answering, was why I made those choices.

As I processed, it came clear that I simply didn’t think I was worthy of love and respect. This was the reason I chose a manic, depressive narcissist as a husband and two criminals who were liars and cheaters as boyfriends. 

I used to blame karma…but that’s lazy. The time had come to take ownership of my own misery. To stop pointing fingers elsewhere and dig into the path to my current state of singledom.

I’ve always felt that being single was a scarlet letter on my chest. I’ve been single now for almost six years with only two awful relationships that were very short-lived. And it hit me like a ton of bricks…maybe I chose those men because I wasn’t ready to love anyone of worth.

Maybe I was forcing myself into the need to have a relationship, instead of the want of one. Being lonely can be a very seductive force causing me to accept men who are not at my level, who aren’t deserving of my love.

I chose men who were troubled; who were opportunists. I had this theory that men who were my age and successful wanted woman who were younger and available (not totally wrong) and young men who were single and younger wanted to have a family (sorry guys, shops closed!).  It seemed impossible to find a partner that matched my zest for life.

These generalities were killing me…and therein lies some of the issue. There is no, single reason why one person chooses another, but there is only one person that will fall in love with you and whom you will fall for…this isn’t economies of scale. 99% of dates fail.

Most relationships are founded on goals; to be married, to have kids, to buy a house. It’s achievement-based, as marriage was based on the premise that women were property and needed a man to care for them.

As women became more independent and self-sufficient, these goals began to change. And at this juncture of life where I’ve been married (epic fail), I have a kid, and I own my home…what is the need for a relationship now? Companionship? I’ve got so many beautiful friends and family that my dance card is filled. Sex? Well, I could have that without the complications of dealing with another human on a daily basis. Sickness? Yeah, it would be nice to have someone willing to take care of me through health issues.

But is that really it? I used to joke with my best friend Gregg that if we are both single by the time we are 50, that he promise to wipe my ass when I can’t, and I would do the same for him. But is this what relationships boil down to, bodily fluids?

To be honest, about 75% of people I know in marriages or relationships are unhappy. Many of them contemplating divorce and envious of my current situation. So why the fuck am I so eager to be in one? I literally have the best life I could have ever imagined and more! Yet, there is that awful pang of emptiness; my life doesn’t feel fulfilled.

At what cost, though, do I continue to torture myself over what is missing. Especially after my last series of dates…I was just done!

After a recent date, the guy I was with talked about installing urinals into his two homes. He was obsessed with urinals as he claimed that it was easier and cleaner for him and his boys. We talked about this for most of the 45 minutes we were together sharing a cup of coffee in the park. He even suggested that there are mechanisms that women could buy and use with a urinal so his lady wouldn’t feel left out.

Come on!!! What the fuck?!

I decided I would finish my coffee alone…so I wished him luck with his urinal installations and finding a woman who would partake. 

It was at that point that I exhaled and gave in. I couldn’t bear the stupidity anymore. Done.

Then I met someone at a party over the summer who piqued my interest. There was an instant connection, our chemistry was kinetic. He’s an actor, comedian, and writer. Just my type; complicated, self-centered and artistic.

We hung out a couple of times, never getting physical, just getting to know each other. But the last time we hung out, we sat in my car and talked for 3-hours following his off-broadway show. During this time, he proceeded to talk about his favorite subject, himself, his ex-wife and ex-girlfriend. 

Once he was finished relishing his genius and all the reasons these women were terrible, he turned to me and said, “tell me about you. Why are you single?”

And that’s when it hit me…as I looked at this man, who was attractive, funny, successful, interesting. He had a lot going for him, and yet I felt NO attraction to the other parts I saw; the selfish aspects of him. These are the red flags I used to ignore as my eagerness to find love blinded me.

I looked him right in the eye and said, “Because I haven’t found anyone worthy of me yet.”

He turned to me, shocked, and responded, “Really? What does that mean?”

So, I said, “Well, it’s pretty simple, I have yet to meet a man that is up to my standard.”

He says, “that’s pretty arrogant.”

I quipped back “not nearly as arrogant as you sitting here with me for three hours talking about yourself and other women.”

Another one bites the dust. But, shit, I walked away from that feeling invigorated and really fucking proud of myself.  This is progress!

Bottom line, loneliness is not worse than being with an energy vampire. I’ve had my fair share, and I’m no longer willing to settle. I was more alone in my marriage than I’ve been while single.  I allowed myself to be taken advantage of because I ignored the blatant signs of insanity. I chose to be blinded by love (or what I thought was love).

No more. The love equation is simple, addition not subtraction. I want someone who adds value to my life; the minute they subtract value, I will subtract them.

This is necessary for my survival and my sanity. After being drained emotionally, physically, and financially from terrible choices, I now choose me.

There was this great quote from Caroline Caldwell I saw recently, “In a society that profits from your self-doubt, liking yourself is a rebellious act.”

And I am nothing, if not rebellious.


Cherry Maggiore is the proud single mom of her 9-year-old super-sassy daughter (aka Miss Sassy Pants or MSP) and 15-year-old pug baby (Tiki Barber); in addition to being an award-winning senior marketing executive at NBCUniversal.

Beside her side hustle as the Freak of Nurture, she also started a home design company after being inspired by renovating and designing her 1880’s home in NJ.

This insanely curious and passionate “multi-potentialite” can be found dancing the Argentinan tango, swing and Hustle every Saturday, cooking her family an Italian Sunday dinner, singing and air drumming at concerts or searching for her next adventure.

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