Chapter 1: Dating in the Grey

Dating is a lot different as a 40-something.  The idea of “happily ever after” has already come and gone.  It’s like finding out Santa isn’t real.  You realize that everything you believed in since you were a kid, was a total farce.  So now what?  What do you do?  What do you look for?  And after getting out of a long-term relationship with the same person, what do you even like?  

The answer is simple, you don’t know.  Or at least, I didn’t know.  I had no idea what I wanted.  Did I want to get married again?  Hell no. Do I want to have more children?  Nope, I am good.  The qualities that I used to look for in a man (wanting a family, being financially stable, a good dad) were no longer the top priority. I have a family.  I am financially stable.  I am a good mom.  I have everything I need.  But I like men.  I enjoy their company.  I like dating and meeting new people.  I want to date.  But what kind of man do I want?

I figured this would likely be a process of elimination.  I would discover things I didn’t like and along the way, take tidbits of the things I was looking for.  Over time, it would be clear what I wanted and what I didn’t.  So that is what I did.  I dated all sorts of men.  I dated the poor bartender, the local Firefighter Captain.  I dated guys that lived out of town and others that lived down the street.  I went on dates with men 20 years older than me and also the youngin’s that were 20 years younger than me.  I found that every relationship was different, but I was constantly the same. 

What I mean by “constantly the same” is that I approached the dating game the same every time.  I would date a couple of people until I started liking one more than the others.  Within a couple of weeks, we were relatively exclusive.  We would start to fall for each other, spend every waking moment together and then find myself in a serious relationship.  It would all happen so fast because, as they say, “when you know, you know”.  But I didn’t feel like I “knew”.  I would find myself feeling trapped in a fast paced, serious relationship within a few months.  I would feel suffocated, trapped.  I would be honest about my feelings and it would eventually lead to a breakup.  It isn’t the right way to date, but I have dated this way my whole life.  Is this old dog supposed to learn a new trick? 

That is when I met Mr. Grey. 

Mr. Grey wasn’t the kind of guy that I would normally entertain.  He was 6 years my junior, relatively short with large hands and feet. 

He had an average build with reddish brown hair that was salted with grey.  The grey hair was the most mature thing about his look. His voice was deep, sexy and had a hint of a southern twang.

His face was cute and boyish.  The type of man who would always look younger than his age.  

We matched online, but I messaged him because we were from the same, sleepy hometown in Florida.  We didn’t know each other but lived close, so we agreed to meet up.  

We were meeting at a local restaurant.  When I saw him, I wasn’t surprised, which is a good thing.  He looked exactly like I expected.  He was handsome but not in a “look at me” kind of way. He had a controlled confidence about him.  He was assertive and manly.  He took charge but was respectful in the process.  He was easy to talk to and it was like we had been friends forever.  The fact that we grew up in the same place gave us an instant connection.  I could tell that he was interested in me about half-way through the date.  His approach was also self-assured and assertive.  He looked me in the eye.  He touched my arm while he was talking and laid his hand on my leg for seconds at a time.  I was intrigued by him.  He surprised me and I loved surprises.  

We kept in touch after our initial meeting and he asked me out again.  This time, I would be meeting him for a picnic in the park to watch the sunset.  When I arrived, he had blankets laid down on the grass.  He brought an insulated bag full of snacks and a bottle of wine.  We laid on the blankets, drank and ate.  The conversation flowed as easy as the wine went down.  I forgot all about the sunset when he stood up and started leading the way.  We hiked up a hill just behind our picnic spot.  At exactly the right angle, there was a bench waiting with a perfect view of the sun dipping behind the mountains. It was a magical moment as I sat close to him on the bench with his arm around me. 

As the sun slowly vanished, I turned to look at him. 

He wasn’t afraid to look me in the eyes, even if we were only inches apart.  His approach was steady and he never took his eyes off mine.  

Our lips met and there was no learning curve. His kiss was firm but his mouth was soft, gentle yet manly. 

We stayed there for a while; talking, kissing and watching the color of the sky change. 

For our third date, we decided to go rollerskating.  It was my idea since I had recently taken my kids.  We both grew up inside the Stuart Skateway so it was nostalgia at its best. He invited me to his place for dinner before we left and I agreed.  He lived in an apartment complex and his place was nice, homey, filled with thriving green plants and impeccably clean.  He had a well-behaved dog that wasn’t allowed to lick my mouth, which I completely appreciated. He made a vegan dish of protein pasta and sauce.  It was delicious.  We ate and chatted.  There was a chemical undertone to our encounter; but I didn’t think much of it.  As we ate on his rainforest-like patio, we greeted the passerby with smiles and hellos.  As we finished the wine, the chemical undertones started to surface and we picked up where we left off on the sunset bench.  I would describe his passion as intense.  He was a man who knew what he wanted and wasn’t afraid to go after it.  I was a woman who was used to being wanted and so I let him chase me through every little touch and peck.  Before things progressed too far, we decided to leave for the skating rink.  

As I got in his car, I was a bit confused.  It was an older ford hatchback and it was as clean as his home.  As we drove down the freeway, I could hear his car making breathing sounds as he manually shifted gears.  The radar detector attached to the windshield dated the entire experience.  I searched for the beeper to match.  Since he was six years younger than me, I wondered if he even knew what a beeper was.  I questioned him about the breathing car and he admitted that he tricked it out with lots of unnecessary bells and whistles while he lived in Florida.  He showed me a flux capacitor looking device in the driver’s side corner.  I started to glaze over as he told me about it.  All I kept thinking was that I was in some sort of time machine, headed to 1982. 

We arrived at the skating rink, put on our skates and began pretending like we were 12 again. 

He brought his own rollerblades.  He surprised me, yet again, with his maneuvering on inline skates. 

He was turning and twisting like an iceskating champion, movements that could only be trumped by a triple toe loop.

It didn’t take a brain surgeon to figure out that he was trying to impress me.  At that moment, he reminded me of my ex-husband; performing for my attention and sneaking glances to make sure I was watching.  To be honest, I was turned off.  Anything that reminds me of my ex, turns me off.  I didn’t pretend to give him my undivided attention.  I made sure that he knew that my eyes were not only his.  I thought to myself, “He deserves a woman who will look at him the way he wants her to”.  I was pretty sure that I wasn’t that woman.  

As we headed back, he asked if I wanted to stop by a bar where his friend was having a birthday celebration. Since I never turn down the chance to meet new people and go new places, I was game.  Since he was younger than me, I was happy in his choice of middle-aged female friends. I liked that he had a circle because I think that is important.  But ever since the “I am not that woman” thought crossed my mind, I felt uncomfortable.  I wasn’t ready to be “his girl” and didn’t know if I even wanted to be.  I felt like I was running away from him the entire night; trying not to lead him on and preparing myself for the “I am not interested” talk. But that chemical undertone started surfacing again towards the end of our date and the sexual magnetism took over. Even though I prepared myself to end things throughout the whole night, I found myself saying internally “just enjoy the moment”. It was selfish of me, but I wanted to experience him while still keeping my virtue intact.  So that is exactly what I did. 

Without turning this story into something only viewable with a paid subscription, I will admit that I underestimated him. 

There was something about him that was intoxicating and he made my experience incredibly enjoyable.

But that didn’t stop me from wanting to run.  After all, “I am not that woman”. 

After our date, he was still chivalrous and consistent with his contact without being creepy and overwhelming.  I knew that I was attracted to him; that we had intense chemistry.  I also knew that we connected as humans; were able to talk easily and had much in common.  But I was pulling away from the commitment that I thought was coming.  I wasn’t ready.  After all, I was tired of my old patterns; jumping in too quickly, falling in love too fast and falling out of love just as suddenly.  This pattern left me feeling like a flawed woman and the men that I left in my trail were quick to confirm by “brokenness”.  I hated feeling this way and I hated the wrath that ensued afterwards from the men whose hearts I had broken.  I wanted to do things differently and so I decided to cut him loose.  

No matter how many dates I have been on with a man or how “not serious” it is, I always struggle with the breakup.  Mainly because it always comes with backlash.  When I received the consistent “Good Morning” text from him, I internally prepared myself for what was coming.  I started with chit chat before revealing that I wasn’t ready for a relationship and didn’t want to give up my dating freedom.  I expected him to be upset, possibly projecting his hurt onto me in small but significant ways.  I expected for our communication to end abruptly as part of the aftermath. I also expected a “hate text” to come through sometime in the near future of our departure.  But that wasn’t the way things went.  Instead, he told me, “I am on the same page”.  This is where things took a turn and became much more interesting. 

It was not the response I was expecting.  From here, we began to talk about the courting process.  He explained to me that he likes to take his time with dating.  He doesn’t just jump into a relationship but rather “vets” the person over a series of months; during which, he continues to date other women.  He felt that this allowed him to really get to know someone before committing, while not subscribing to a “scarcity mindset”.  Scarcity mindset applies to the idea that when you are in the initial stages of dating, you begin to commit early on.  With this commitment comes an elimination of choices.  He explained that this process tends to make people feel clingy and possessive; something that I have felt from men in almost all of my recent relationships.  By committing to the act of dating, it allows each person to have choices; therefore, not settling for the easiest and most convenient choice, but rather, the best choice.  He further explained that his “vetting” process lasts about 6 months, the amount of time that is recommended to really know someone.  At six months, if he has found one woman that he is significantly interested in, he has a conversation about becoming exclusive.  

I asked questions like, “Do you reveal to the women you are dating that you are seeing other people?”

“Yes, absolutely.  Honesty, transparency and open communication are key”, he said.

“So, if I wanted to date other men, I could still date you?  And I wouldn’t have to lie about it? And you wouldn’t feel jealous?”, my inquiry continued. 

“I encourage you to date other men.  That way, you won’t get too focused on just one person”, he replied. 

This man was blowing my mind but also creating a lightbulb moment.  What he was suggesting wasn’t that crazy if you think about it. After all, they say it takes about 6 months to get to know a person.  Why would you commit to someone you didn’t fully know?  And if you had an option to get to know a person before committing, doesn’t that seem like the right way to date? Mr. Grey called it “Dating in the Grey”, apropo to the nickname I had given him.  He explained that most people date in black and white, single or taken.  But there is a wide area between the two that he referred to as “the grey area”.  This is the area of exploration, adventure and knowledge.  The very place that connects the areas of black and white; or rather single vs taken.  He liked to “live in the grey”; concentrating on open communication, pacing and living an abundant life.  

I was intrigued and a bit terrified by this curveball he threw at me.  While I didn’t want to commit to a relationship with someone I didn’t know, would I be able to date knowing that I wasn’t the only woman?  Would I be comfortable dating multiple men at once?  The idea of “committing to no commitment” wasn’t something I had ever done before.  And I definitely knew that my current dating practice was creating unhealthy patterns and even unhealthier relationships.  Maybe this is exactly what I needed to do? 

Mr. Grey was onto something.  It was unconventional yet exciting. 

The conversation had an impact on me; so much so, that I decided that I wasn’t gonna end things with him.  Instead, I was going to try his way of dating. 

I was going to “date in the grey” and in the process, write about the experience. 

So here I am, taking a vow to “commit to no commitment” for the next 6 months.  

But if I was going to do this, I need to establish some ground rules. The plan is not immediately give myself to every eligible bachelor I see potential in.  That’s not my style.  My plan needs a plan………

Next: Chapter 2 “Rules of Engagement”.