It has been four months of “Dating in the Grey”.  What started as a few casually hilarious dates with some random ding dong men has turned into a love battle between two viable prospects.  In one corner, I have Mr. Grey; the womanizer who I am trying to tame.  In the other corner, I have the Writer; the perfect on paper guy who I am searching for depth.

So when the Writer asked, “When can I see you again?” I agreed to a third date because I still didn’t feel like I knew him. Why would I? He was a stranger three dates ago.

What I did know is that I didn’t want to have another dinner or drinks date with the Writer.  I wanted to share an experience with him; go on an adventure.  After all, this guy was starting to bore the hell out of me but I didn’t think he was a boring guy.  I attributed it to his newly single life and being “fresh off the divorce boat”.  But one thing I was really good at was thinking outside the box and doing things that can create a lasting memory.  

“How about this weekend?”, I replied. 

“Great. Let’s get together Friday night”, he said.  

As soon as the letters appeared across my screen, I let out a big, disappointed sigh.  “Another dinner” I thought to myself, which meant “another predictable snoozefest”.  

I knew I had to tread lightly so I didn’t damage his ego, a fragility in most men.  I didn’t reply right away because I wanted him to sense my hesitation, but before he could lose interest or royally freak out about my lack of communication, I reached out. 

“I am free Saturday afternoon as well”, I simply said. 

After about 32 minutes and 7 seconds, what seemed like the exact amount of time I left him waiting, he responded.

“Let’s do something fun on Saturday” he wrote. “I am free during the day and would love to take you on an adventure”

Adventure is my love language and the Writer was finally speaking it.  It looks like my not so subtle hints worked.  

“Sounds fun!  Can’t wait” I replied. 

My mind immediately began imagining ideas of adventure grandeur.  I thought about all of the things we could do near where he lived.  A pitstop at a wine bar before we toured an art museum.  A game of paddle tennis followed by brunch.  An afternoon by his pool coupled with cocktails.  Before I could think of another fun daytime activity, I remembered that I had concert tickets for that night. 

Since the concert was within close proximity to the Writer’s home, I was hoping he would join me and a bit disappointed to learn that he had previous plans.  Maybe it was for the best.  After all, I only knew one song by this band and I wasn’t even sure I liked the rest of their music since I hadn’t heard it. I began thinking about who I could invite and that is when I thought of Mr. Grey. 

It had been a couple of weeks since my “elevated man” speech to Mr. Grey and I was starting to see a change in him.  Instead of lining up dates every week with different women, he spent his free time in the gym and riding his mountain bike.  And during the nights and weekends that I was free, he spent his time with me. 

The ironic thing was that our lives seemed to reverse roles. While he behaved himself, I was misbehaving with the Writer.   There was a part of me that felt a bit hypocritical, but the other part of me felt that it was simply my turn.

“Are you free Saturday night?” I texted Mr. Grey “I have concert tickets to see a band that I barely know.  Want to come?” 

“Sure. Sounds fun” he replied immediately. 

A smile lit up my face.  One of the things that I was learning about Mr. Grey is that he was always ready for whatever adventure I threw at him.  He didn’t care where it was or who it was with, he was a “yes” man.  

Quickly, my excitement dissipated when I started to realize that I just planned to see both of my dating prospects on the same day; literally one right after another.  

“Shit” I muttered to myself.

As the weekend approached and I prepared myself to be the female version of Hugh Hefner, I received a call from Mr. Grey. 

“Woman” he said, a common way he greeted me which I have grown to love. 

“Man” I replied because I believe in equality in salutations.

“So….something interesting happened today” he began “A headhunter reached out to me about a job for a major manufacturing company”.

“That is amazing!! How did that happen?” I replied.

“They found me on LinkedIn.  I wasn’t even looking but I spoke to the headhunter and I totally impressed her with my background in tech at my old job and then my experience with manufacturing apparel at my last company.  She is going to set up an interview with the company this week” he continued. 

I could hear the downplayed excitement in his voice.  We had talked about his current job and how miserable he was.  As part of my “elevated man” speech, I encouraged him to find a job that challenged him and allowed him to use his most valuable attributes; attributes that he currently underutilized at his current position.   I don’t know if he was more excited for this opportunity or if I was. 

“Oh my god! That is so wonderful.  Congratulations” I replied. “And I want to take credit for pointing out that you need to get a new job.  I manifested that shit for you.” 

“Yeah, you called it” he said without giving me too much credit.  “Alright, I just wanted to share the news with you” 

“Congrats again and let me know when they schedule the interview!” I said before we hung up.

This was a step in the right direction.  I always believe that one small change would lead to big changes and maybe this could be the thing that allows him to be the man I see in him. The man I know he can be if given the opportunity; not just for me but most importantly, for him. 

When Friday came, I wondered about my surprise date with the Writer so I reached out.

“Hi!  Excited to see you tomorrow.  What time do you want to get together? And what should I wear/bring?” I wrote. 

“I figured we could go on a hike and then go to brunch, so wear something comfy to walk in.  And bring a bathing suit cause we can cool off in my pool afterwards”, he replied. 

Although his “surprise” was more of a dating profile cliche often listed under “things I like to do”, I wasn’t going to complain because anything was better than a dinner date. Plus, I never turned down an opportunity to get in a pool. 

“Sounds fun! What time you thinking?” I wrote.

“How about 10am?” he said “you can meet me at my house and we can ride together. You can park in the driveway.” 

I always thought it was funny how you needed an invitation to park in a driveway in LA.  It was something I found odd since I grew up thinking that driveways were places where you SHOULD park.  With limited parking, a driveway in LA is like valeting your car so only the most exclusive guest were invited to share in this experience.  I suppose I was rising on the Writer’s “VIP” list since I have quickly moved from street parking to a space in his front yard; the universal sign for “we are dating”.

“This might demote me to street parking” I thought. 

I made my way to his classic, “gone with the wind” style home and knocked on the door.  As the door opened, he greeted me with a warm smile and a tight hug while he ushered me inside so he could grab the rest of his things.  As I stood there watching him, I couldn’t help but notice his odd choice in apparel.  He looked like he was auditioning for the role of Scotty Smalls in the movie “The Sand Lot” in his weird, long brimmed hat that lacked any kind of stability at the top; just a form fitting dome that hugged his head like a condom.  His shirt was less offensive because it was a generic t-shirt. However it hung over his barely there shorts.  He looked odd, to say the least; a far cry from the stylish man I met on our first date.  He sat down to put on his equally clashing running shoes and we left the house like he was about to appear on “What Not to Wear”.  

We began making our way to his car and as he passed mine, he said, 

“Thanks for taking out my planter” with a smirk.  “Next time, try to park on the driveway, not on the plants”.  

Apparently, he was more observant than I gave him credit for and I may owe him a few plants.  

“You didn’t need that planter anyway” I said with a smile as I opened his car door and parked myself in his passenger seat.  

As we drove to the undisclosed hike he had planned, we began typical small talk that didn’t involve planters.  He updated me on his work and the shenanigans with his son.  I desperately wanted to move past the small talk so I started asking him some intense questions to see if I could pry any kind of vulnerability out of him.  

“So how has dating been going for you? Still fighting off thirsty women?” I asked in a tone that was clear my questioning wasn’t coming from a place of jealousy but rather inquisition.   

He let out a big sign and rolled his eyes. 

“It is crazy out there in the dating universe.  The women are so hungry for commitment”, he replied. 

I was hoping that we would divulge some juicy details about his experiences but instead he said, 

“If you or I decide that we want to date other people, I think we should just let each other know”

Silence filled the car as confusion wrote its letters across my face.  The truth was that I was dating other people.  I had told him from the beginning that I was “committed to no commitment”.  We talked about it.  So why was he assuming that I wasn’t dating anyone else?  Or was this his passive-aggressive way of asking if I was seeing anyone outside of him?  

While I was contemplating our miscommunication, the Writer had changed the subject and was rambling about something that had completely gone over my head.

While I stared at him blankly, I said to myself,  “If you don’t know what to say, don’t say anything at all.” 

I needed some time to mull over the idea of telling the Writer about Mr. Grey.  I didn’t know how to tell him.  Do I just blurt out, “I am dating someone else”?  I am sure the knowledge of competition will only instigate further questioning.  Will I tell him its none of his business?  Do I tell him the honest truth?  

“You ok?”, asked the Writer as he snapped me from my thoughts and back to reality.  

“Yeah, you ready?” I asked after I noticed that he had parked the car and was waiting for me to get out.  

“Let’s do it”, he said as he grabbed the long bill of his ridiculous ball cap in agreement.  

The “hike” began on a sidewalk of a crowded street.  It was a weird neighborhood, the type where it is residential on one block and then boom, strip mall.  As we passed the pop up strip mall, the Writer commented about a small breakfast spot. 

“I eat there all the time.  It’s so good”.  

“The hike is just up here” he said. The street transformed to a storybook setting.  There were rows of cottage-like houses with perfectly manicured lawns.  Every few houses would be a larger house that looked like Repunzel would let down her long hair at any moment. 

“You see those stairs?” He said as my eyes search the cobblestone wall in search of a staircase.  It was like playing the HGTV version of “Where’s Waldo”.  Then, in between a large Repunzel house and a small cottage was a narrow staircase that disappeared into a forest-like tunnel of trees.  

“Those stairs are actually public walkways.  They take you to the streets located higher on the hills.” He said.  

“We should go explore and see where they take us!  It will be like a scavenger hunt but the prize is breakfast”, I said.  

I don’t think he realized that I was being serious and kept walking down the narrow paved road.  

I followed him like a lap dog, trailing as fast as my little legs could carry me.  As we continued down the road, the houses disappeared and the trees took over.  We were high on the hill and as we turned a corner, a giant reservoir appeared at the base of the small mountain we were climbing.  I could see people walking around the giant hole filled with water.  The Writer explained how he considered taking me on a hike around the reservoir but decided that the view from the top was more impressive.  

“I wish I had my phone so I could take a photo.  It is so beautiful up here” I said when I realized that I had accidentally left my phone in the car.

“Everyone is so attached to their phones these days.  Social media is destroying society.  Did you watch that Netflix documentary “The Social Dilemma”?   These companies are using social media to manipulate people. It is disgusting”.  

I kept quiet while he had his soapbox moment.

“I guess this would be the wrong time to tell him I’m an influencer”, I said to myself. 

I was beginning to feel that leaving the conversation up to the Writer was not going to get me any closer to connecting with him. So, I began asking him questions in hopes that I would find a hole in his walled up heart. 

“Are you parents still alive?” I asked since I figured I would start at the beginning of conception and work my way through his 42 years.  

“Yes, my dad lives in New Jersey and my mom lives in California” he said matter of factly.  

And then he changed the subject and started to babble on about the reservoir for what seemed like eternity, so I turned the conversation toward sex. 

“What is the craziest thing you have ever done in the bedroom?” I asked, hoping I would get a shocking answer that would lead me to believe that he wasn’t as vanilla as he seemed. 

“What do you mean?” He questioned like I was asking him to solve quantum physics.

“Have you ever experimented in bed? Slept with more than one person at a time?”  I admit, I was fishing for any sign of his stance on such things because of my situation with Mr. Grey. If I was going to tell him, I needed some inclination of what his response would be. 

“In college, I was at a party.  I walked into a room and there were two girls and a really good friend of mine, just hanging out. After a while, one of the girls asked if I wanted a blow job.  I figured, “what the hell?” So I said ok.  Then we all started to hook up.  It was wild”, he said. 

“Have you had any experiences like that since college”, I continued to inquire. 

“No, that was my only one” he shared and then continued walking in front of me like he was running away from the conversation. 

His answer did not make me feel any more comfortable about the news I was thinking of sharing so I continued to keep my mouth shut. 

As we made our way around the reservoir and down the mountain,  I didn’t press him with any more random questions.  Instead, I just listened. Most of what he talked about was completely surface but then, there was a moment where the tone in his voice changed. 

“Do you ever dream of moving out of LA?” He asked. 

“When my mom died and I learned about my husband’s affair, I couldn’t imagine living in LA as a single mom. Since I had inherited our childhood home in Florida, I thought I would move back home.  I tried to for several months, beginning a court battle with my ex so I could go back to where I came from.  But after a few months, I got the opportunity to appear in a workout program.  I would make money and work on myself at the same time.  It was a turning point for me because I realized that I COULD make it in LA as a single mom.  It made me think that I was meant to be here.  Everything I am passionate about is here.  And while I will always be a small town Florida girl, LA is my home now.”

My prolific speech about my life didn’t resonate with him at all.  

Instead he said, “I think I want to move to Lake Tahoe. It is so pretty and quiet there.  You don’t have helicopters flying over your house constantly or homeless.  That is why I kept my house.  The only place that feels quiet and calm is my backyard.  Plus, it was really mine and my son’s home.  My wife was always traveling or off at some work function.  She was a high-level movie executive so her job was pretty intense and kept her away from home a lot.  It’s probably the reason for our divorce.  I always had to be second.  Everything she wanted was a priority over what I wanted.  I am tired of being second.”

It was probably the most vulnerable thing he had told me thus far.  It explained a lot about him.  It explained why he tortured himself living in a place with so many memories;  it was his only escape.  It explained why he was so closed off; he was trying to make himself a priority.  It also explained the lack of spice in his life; he hadn’t focused on himself in a long time. This small yet significant insight made me feel for him.  I wanted to show him that life after divorce can be wonderfully fulfilling.  I wanted him to see that escaping a home or a city wouldn’t solve his problems; those are internal wounds that he needed to heal.  I wanted him to feel wanted and seen. When I looked at him, despite the horrendous outfit choice, I felt like I could see him for the first time.  

“What about your son?”, I asked.  “Would you move away from him?”

“No way.  But once he goes away to college, I am out of here” he said. 

I could tell by the tone in his voice that he was bruised by LA.  This city can do that to you.  It is the land of opportunity and that is what makes it magical.  But it is also the land of expiring dreams and lost possibilities. The highs are higher than the sky, but the lows seem like you are buried in the ground.  People come here thinking they will live a life straight out of a romantic comedy.  But have you ever seen a romantic comedy that was stuck in traffic the whole time?  Me neither. Welcome to LA.

“You don’t have to move out of LA to gain more quiet and calm.  Where I live is pretty quiet.  There aren’t helicopters flying overhead or vagrants wondering the streets constantly.  It is nice in the valley, suburban.”, I said.  

The moment the words left my lips, I could feel him closing off again.  It was like I was stealing his dream by proposing practicality.  He didn’t want to hear it.  He believed that a change in location would solve his problems.  What I knew from my time post divorce was that it doesn’t work that way.  Your problems will follow you, no matter where you live if you don’t face them.  He was looking for a way to run away, which explained his constant pace two steps ahead of me. 

We made our way down the mountain and to a breakfast spot.  I was starving at this point and in need of coffee, stat.  We looked around for a menu or waitstaff to help us.   When someone finally appeared, she directed us to scan the sticker code on our tabletop.  Since neither of us had brought our phones, we asked for a menu. 

“I guess phones aren’t the bane of social existence after all” I thought to myself. 

We finished our food and I paid the bill since he forgot his wallet in the car.  As we drove back to his house, I thought about what would happen once he had me alone. 

We stood in the expansiveness of his living room and he began to unload his belongings and headed to the kitchen to make us a couple of cocktails.  I was flattered that he remembered my drink of choice and made it without prompting.  I could tell he was more comfortable within the walls of his home.  His presence seemed lighter and more carefree.  

“Alright, do you want to go upstairs and roll round for a bit before we head to the pool?”, he asked.

I was a bit surprised at his forwardness, but I supposed I enjoy a man who knows what he wants. 

“Why don’t we go hang out by the pool first?  Finish our drink and just chill for a while”, I suggested. 

“Nah, it is best to get sweaty first and then go in the pool”, he said.  I knew that I wasn’t going to sway him and I figured that I would give him a second shot to please me; since the first time wasn’t very satisfying.  

As I made my way upstairs, I felt like I was having deja vu.  There was no seduction in his process; but merely, a checklist of “to-dos”.  As he moved from one check box to another, I was starting to lose interest.  He could sense my departure and he started to step it up, introducing some “outside the box” maneuvers that reinvigorated my enthusiasm.  

“Maybe he isn’t so boring after all”, I thought. 

I knew that I couldn’t rely on him to satisfy my craving so I took matters into my own hands. As I took charge, I could tell that it turned him on.  He was a very good student; following my instructions like a teacher’s pet.  After a few minutes of playing teacher, we both layed in a panting heap amongst the covers.  

“Now I am ready for the pool”, he said with a smile of satisfaction on his face.  

“About time”, I thought to myself. 

I gathered my belongings from the floor, which currently resembled a yard sale of clothing.  I tiptoed downstairs so that I could put on my bathing suit without provoking “round 2”.  As I exited the small powder room located on the main floor, I was equally surprised by outfit choice number 2. If I thought his hiking shorts were short, his bathing suit choice would practically get him arrested in public. They were somewhere between a speedo and bike shorts.  I could tell he was proud of them because they highlighted his best kept secret; or so he thought.  He stood  shirtless in his bootie shorts in the hallway, but the shorts were the least offensive part of his so-called outfit.  As my eyes made their way to his face, I noticed a white bucket hat on his head that reminded me of my grandfather’s fishing hat.  It was one of those hats that had a short, 360 degree brim. And then, my eyes laid on the most offensive part of his outfit , a very large pair of tie dye crocs.  Thank goodness we were only going to the backyard. 

I followed him out to the backyard with my cocktail and found a comfortable chaise lounge to sunbathe on.  As I looked back at the Writer who was standing on the porch behind me, I couldn’t help compare him to Uncle Eddie in National Lampoons Christmas Vacation.  All he needed as a hose, a cigarette and a wild line about emptying the shitter. 

While we lounged by the pool, our conversation was much of the same; simple small talk to pass the time.  Since I had another date with Mr. Grey that night, I had to be cognoscente of the time and when the clock hit 3pm, I said adieux and drove off into the early evening sky. 

I felt like the day should be winding down, but it was just beginning again with  a concert to attend and Mr. Grey to join me.  As I drove home, I called Mr. Grey to give him an ETA of the arrival at my house.  

“Hey”, he said after picking up the phone on the first ring. 

“I am on my way back. I should be at my house in about 30 minutes.  I still have to change but do you want to meet me there?” I suggested.

“Yeah, I checked the directions and it said that we should leave around 6:30pm if we want to make it there by 7pm”, he said. 

I smiled to myself.  Mr. Grey wasn’t much of a planner when it came to adventures.  He was a man of routine and he liked to stay in one place.  You would think that we would be an unlikely partnership since I am always planning things to do and on the go; never staying in one place for too long.  I had never dated anyone that didn’t match my enthusiasm and adventurous spirit.  But what I was learning though my experience with Mr. Grey was that this dynamic worked too.  In fact, at times, it worked better than the relationships with men who were my clone.  I had the freedom to explore wherever I wanted and I almost always had a willing and able partner to join me.  Because he was along for the ride, he rarely complained about where we were or what we were doing.  He always had fun, even if it was just by watching me buzz around the room; making friends and introductions, everywhere I went. 

I rushed home and started washing off one man in preparation for another.  

“Man, this is exhausting”, I thought to myself.

As I was in the bathroom, putting the finishing touches on my makeup, I hear Mr. Grey open the door and let himself in. 

“I’m up here!” I yelled.  “Come keep me company while I finish getting ready”

He quietly walked up the stairs and I checked him out as he did.  I never truly appreciated his sense of style until this very moment.  His pants were tight, hugging his muscular legs.  He wore a white long sleeve button down shirt that fit his frame perfectly. His salt and cinnamon hair was standing up in all of the right spots and his shoes did not consist of crocs; but rather, dress shoes that tied the outfit together perfectly.  

“Hey” he said as he went to sit on the stairs, across from the bathroom door

“Get over here and kiss me”, I demanded.  He smirked and gladly obliged.  

As we drove down the famous freeways of LA and entered the heart of the city, I could see Mr. Grey take in the sights. “Have you ever been to this part of town before?” I asked

“No.  This if my first time.  It is so congested and so much going on”, he observed. 

Mr. Grey had lived in LA for three years but he had barely left the confines of the sleepy little suburb he called home.  “Better late than never” I thought to myself as I parked my car and led the way down the bustling city street. 

We wandered around the massive venue and peaked in at the staging area on the opening act.  It was a young woman, literally standing on a wooden box, chanting about female oppression.  We quickly turned around simultaneously and said in unison, “Let’s go get a drink”.  

Once we were sufficiently lubricated, we found a set of couches to sit and chat while we waited on the main attraction.  

“How was your date with The Writer”, Mr. Grey asked. 

“It was ok.  I am still unsure about him.  But something happened today that kinda made me think that I need to tell him about you.” I said. 

The very mention of his own name made Mr. Grey pay extra close attention. 

“What happened?” Grey asked. 

“We were driving in his car, on the way to a hike and he said “I think we should tell each other if we start seeing other people””, I said and I waited a beat to see Mr. Grey’s reaction. 

“What did you say”, Mr. Grey asked. 

“Nothing!! I just sat in there in shock.  I mean, I told him that I was dating other people before we even went on our first date.  I explained the whole philosophy of “Dating in the Grey”.  He asked me questions about it and even complimented me on giving such great dating advice.  But now it is like I never said anything.  I think he’s assuming that I wasn’t seeing anyone but him and he wants to know if that changes.  But I have been seeing you before I even met him and now I don’t know what to do.  Do you think I should tell him?” I asked.

Mr. Grey sat there for a second while he thought about his answer. 

“In my experience, honesty is always the best policy” he said “If you are honest, than you give people the opportunity to choose if they want to proceed with you or not.  But if you lie or withhold the truth, it is misleading and allows for assumptions which is never a good thing. 

I knew Mr. Grey was right.  The thing I loved about our relationship was that it was based on utter and complete honesty.  Learning how to be honest within a relationship hasn’t been easy because I have always been afraid to disappoint or hurt the person I am dating.  But I have found that Mr. Grey was right.  Honestly weeds out people.  There are those who can handle the truth and those who run away from it.  If I wanted to have an honest and vulnerable relationship with The Writer, this was my opportunity to pull back the curtain, make myself vulnerable and be utterly honest.  

“I think the band just came on” Mr. Grey said as the blaring of the music started to make its way down the hallways of the venue.  

“Let’s go check it out!” I said with excitement. 

Since I only knew one song by this band, I had bought the “cheap seats” which meant standing room only.  As we entered the main floor, there were people everywhere and the entire space was packed.  

“Let’s go sneak upstairs and see if we can find a seat” Mr. Grey said. 

“Ok” I responded as I followed him upstairs.  

I felt like we were sneaking out of our parents house as we made our way to the upper balcony.  As we looked around, there were so many empty seats.  We grabbed two that had the best view and began taking in the show.  

“This is fun” I thought to myself as I glanced at Mr. Grey. 

“Isn’t it a good song?” I said as I bounced around to the beat of the music.

“Yea, its good” Mr. Grey replied, more amused by my excitement than anything we heard in the venue that night. 

“Thanks for coming with me”, I said as I leaned my head on his shoulder as we walked side by side out of the venue.

“Thanks for bringing me.  It was fun”, he said as he squeezed my hand. 

As we made our way back to my car, I took a moment to take in my surroundings and appreciate my life.  I was a strong, independent, forty-two year old woman who had a great job, good self esteem, two kids that she adored and two men vying for her attention.  Life was pretty damn good at the moment and it was about to get a whole lot better once I returned to the place that makes my heart pump, my skin sweat and my eyes roll back in my head. A place that only Mr. Grey knew how to get to.

The rest of the weekend I kept debating on whether I should tell the Writer that I was seeing other people.  I know that Mr. Grey encouraged me to be honest but I was still hesitant.  I would spend hours trying to convince myself that I didn’t need to say a damn thing, but the fact that I couldn’t stop my internal contemplation was the answer I needed.  The truth was that I wasn’t going to stop stressing over it until I told him the truth.  I knew it was the right thing to do.  And I knew I wanted an honest relationship.  How would I ever have honesty if I wasn’t willing to be honest? It had to start with me, right now.  

And just as if his ears were ringing, my phone pinged with a familiar text from the Writer

“When am I going to see you again?” he wrote

I took a big long breath and started to text him back, 

“This week is crazy cause of work.  But there is something that has been weighing on me that I want to talk to you about.  When we were driving to the hike, you said that we should tell each other if we start to see anyone else.  Well, I have been seeing other people.  I kinda got the vibe that you assumed otherwise so I want to be transparent.  And if you want to talk about it, I am happy to do so.”

Not even one minute later, my phone rings.

Here we go…

Chapter 8:

The Verdict