Fifty-ish and Dating 2022

Some may say the dating pool is bleak for 50 and over, I have no choice but to look at the dating pool as half full. I think everyone can have a piece of the love pie! The first step is changing your negative perception into a positive outlook of what's at hand. Define your goals in detail by asking the questions: What do I want in a relationship? What type of relationship am I looking for? What are the top five qualities I am looking for in a person? Getting to this healthy outlook was not an easy part of my journey.


My divorce was final May 17, 2017. I really didn’t think too much about it I felt relieved and excited to be able to start over. Starting over should’ve been a red flag because in my mind I was only thinking of finding the perfect relationship. I wanted to prove to myself that I could be successful at having a healthy relationship. Not realizing a healthy relationship can only come from a mentally healthy person. Unknowingly I wasn’t so emotionally healthy and need time to heal before venturing out to search for Mr Right. This part of my journey I will divide it up into quarters. My journey from the time I was divorced until now. I look back and I’m thankful for every lesson learned.


After my divorce I felt a sense of freedom a sense of a second chance to prove to myself that I could love and be loved in a healthy manner. Prove that my estranged husband was the cause of all of the toxicity in our marriage. It didn’t take long for me to venture out and land myself into my first romantic relationship quickly after my divorce. I jumped into a romantic relationship, this time with a younger man who was different in every way from my estranged husband. Height, appearance, race, religion, financially, and in age. He was 19 years younger than me and age was not a limitation for me in my mind it was just a number. Our relationship lasted for approximately a year. Wasting no time three weeks later I met a gentleman 10 years my senior, handsome, gray, and well dressed. That encounter lasted for about six months. I wasn’t through I still wanted a relationship. I was familiar with dating websites and thought possibly this would be a chance for me to find Mr. Right. I met a man on a dating site he seems to be gods gift. He was my age a month younger than I was, tall with salt and pepper beard and hair he was intelligent and seem to be loving. He would be the last of my continuous cycle of dating without the proper tools. It turned into a mental and emotional roller coaster that lasted for all of another torturous six months. Our relationship ended with me near an emotional breakdown. This was in 2020 right before the onset of the pandemic.


The onset of the pandemic made it quite easy to be with myself. I knew that I had work to do and settled into the realization that this would be part of my journey I would have to experience alone. In the beginning I felt lonely I wanted to be in a relationship and the idea of just dealing with me as an uncomfortable thought. I wanted someone to take my mind off of myself I wanted to be in what I called in LOVE. I was lonely. I quickly learned that being lonely and being alone were two different things. I felt a void in my life. The void was ME. I was missing Me. I remember taking one day at a time. Although it was a pandemic I still managed to get out in nature and take walks. On these walks I began to have conversations with myself being totally honest with myself and playing back the roller coaster that I had been on for a long time. Forgiving myself for neglecting my spirit. Forgiving myself for looking outside of myself to feel whole. I knew I had to do the self work, and it was hard. One day became two days, two days became 30 days, 30 days became six months, six months became a year. I had officially become single mind,body and soul. It felt great, for the first time in my life I felt free of my emotional bondage.


I felt free and could care less about dating or having a romantic relationship with a man. I started directing my energy on me. Getting back into the hair industry completing my novel, “Love Addict “. I was avoiding any contact with men, if I did talk to a man it was strictly non-sexual and on the friends basis. It was my way, my rules the boundaries that I set. It felt good to be in charge of my emotions. I thought I was doing great and in a lot of ways I was. It had been over a year since I had romantically dated anyone and something was happening. I started to avoid romantic relationships altogether. It was easier than trying to figure out another person, easier than putting my heart on the line. The uncertainty of a relationship and getting hurt placed a fear in me. I became safe and content in my bubble. In my year and a half of being totally single I started to question why was I avoiding relationships I started to feel I had gone to the extreme of not dating. One day reading about love addiction I ran across the word avoidant. Love Avoidant someone who avoids intimate contact with others in terms of a romantic relationship. I had went from one extreme to the other.


It have been a year and a half and I still had work to do. What I thought was a complete healing was just part of my healing process. I had to find balance unknowingly that was the trickiest part of this journey. The walks continued and my perspective changed my conversations became more detailed. The question: What am I afraid of? The answer: ME. I was afraid that the part of me that was emotionally dependent would rear her ugly head once again and I would become the toxic element of any relationship I decided to have. The conversations with myself made me aware of my feelings. Writing down the qualities that I was looking for in a mate. It didn’t take two or three red flags the first red flag was a dismissal of any possibilities of a relationship. I became in tuned with how I was feeling. I did stumbled along the way but the balance came back and I’m ready to experience a healthy relationship. So at 50-ISH, I’m a new me experiencing one moment at a time. It’s plenty of choices out here, no matter what age, you just have to be willing to be content with yourself whether you are in a relationship or alone. Remembering that being alone does not mean you’re lonely it’s a choice.

E.S. Bailey

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