Chapter 9: Will He Stay or Will He Go?

When I started this journey of “Dating in the Grey”, I thought it would be my own version of “The Bachelorette”.  I pictured myself with more suitors than I could imagine; all of whom would offer me a “happily ever after” where I would choose which ending I wanted for my future.  But being a long-time television producer, I should have known that “real life” does not emulate fairytale television.  And as I spent the last six months living this journey, I realized that there were no fancy hot air balloon rides, no private serenades by Michael Buble, and certainly no proposals (thank god).

What I did experience was something unexpected.   I had many suitors but they weren’t the knock off Prince Charmings that I pictured.  There were men that I thought were sweet and innocent; only to be surprised by the announcement of “I am going to ejaculate” during our first kiss.  There were men who I lacked any kind of chemistry but this admission was followed by a slew of “hate texts”.  There were men whose own traditional “boxed in” mentality fought against my science experiment of “Dating in the Grey” and the notion of “other men” was an instant deal breaker.  But the most surprising twist of events was Mr. Grey.  He was the man who I blew off in the beginning but who would become a constant presence throughout my journey.  And while “Dating in the Grey” was his idea and philosophy; I gave it purpose, the proof to his pudding.  And while I lived the experiment, he counseled me through it while we explored each other in every way imaginable.

It wasn’t the type of relationship I ever pictured for myself. 

There were several moments where I wanted to throw in the towel and “block and delete” him from my life.  But each time I waffled with the decision to “stay or go”, there was something that always kept me from closing the door entirely.

It wasn’t the type of relationship I ever pictured for myself.  There were several moments where I wanted to throw in the towel and “block and delete” him from my life.  But each time I waffled with the decision to “stay or go”, there was something that always kept me from closing the door entirely.  Perhaps it was his calm and stoic nature, maybe it was his ability to listen and learn or it might be the dedication to the process of “Dating in the Grey” and seeing it through til the very end.

The hard moment of hurt traditionally were the times I would run away.   I have become a Usain Bolt-like sprinter from situations like that.  But because there was no commitment between Grey and I, it added a different layer to the decision making process.  I didn’t have to decide if he was my “one and only”.  And many times, I stayed because I still had the freedom to find someone better suited for me.  The idea of “having my cake and eating it too” crossed my mind more than I would like to admit.  And in those times of conflict, I didn’t care what he thought of me or if it was a breaking point between us.  I splattered my hurt feelings and my truth all over him.  And he always stood still, like a statue as my emotional paint messed up his OCD ridden routine.  It was a “push pull” kind of dynamic that would drive a wrench through us and then create an unparalleled level of closeness.  It wasn’t the kind of connection I had ever felt before; mainly because I had never experienced the kind of honesty that we shared.  We told each other everything; even the things that were hard to admit.  He never made me feel judged or ridiculed.  He allowed me to grow as a woman and supported my dream to share my story; even if it was at his own expense.  And those “shiny pieces” of him that I first noticed, were not fleeting bits of dust, but were the fabric of his being.  Those were the pieces that initially intrigued me and that I grew to love the most.  And the more I learned about him, the more I realized that there were lots of those shiny pieces; doled out over time and with great care, only to those whom he felt safe enough to share. We grew together through this beautiful journey; pushing each other to explore everything we wanted in life.  And now that the six months were coming to a close and I thought we would have the “talk” about where our relationship would go from here; he threw another curveball my way that was completely unexpected.

“I was headhunted for a job in Napa” were the words that would hit me like a ton of bricks.

“Napa?” I thought.

I knew that he was feeling stuck at his current job and needed a change. But moving six hours away to a different city entirely did not cross my mind until this moment. I wanted to say that I didn’t want him to go.  I wanted to say that if he really cared about me and what we built together, he would choose to stay.  But each time the words left my brain and sat on the tip of my tongue, I couldn’t let them slip.  They weren’t true.  I didn’t want him to sacrifice himself for me.  I wanted him to have everything he ever wanted in life and more.

Grey explained how this job was a long shot for him.  It was a global company that was interviewing candidates from all over the country to fill the role.  But Grey admitted he needed this challenge.  He had big dreams of becoming a Richard Gere/Pretty Woman type businessman and he wasn’t going to do it if he stayed at his current mom and pop owned printing company.  He needed a big opportunity to do big things and this was that kind of opportunity.

I listened to him explain the perks of the job as I let the reality set in; Grey might move away.  It took me a minute to figure out what was the most truthful, authentic thing I could say. And then I knew and I looked him straight in the eyes and said,

“If that job in Napa is what is going to make you feel like the extraordinary man that I see in you.  Than you better go get that job”

I kept my soft hands, wrapped around his face and I kissed him in a way that I didn’t kiss him often. 

It wasn’t full of passion and chemistry. 

This kiss was full of love and acceptance. 

The kind of kiss that feels like a hello and a goodbye at the same time.   And as our lips parted and I looked in his eyes again, he gave me his boyish grin and said,

“That job is mine”

I knew he was right. After all, he accomplished everything he set his mind to.

“You have lived in LA for three years but you have never really seen a lot of LA, have you?” I said.

“Not really”, he replied.

“If there is a possibility that you may leave, then I am going to give you something to miss. I mean, more than me, of course. ”, I said with my own girlish glimmer.

In a way, I was relieved that he might leave. 

I know that sounds ridiculous to say after my “I don’t want him to go” tirade. 

But the other part of me, the part that was scared to love somebody; the part that was scared of being hurt or rejected or tossed aside for a new shiny object; the part that didn’t want to give up my freedom to date and explore; that was the part that made me feel like this would be a good thing. 

It would allow a natural closure to a relationship that I wasn’t ready to end.

Maybe it would allow me to let go in a way that was less painful; a way that would allow us to still remain friends and maintain some semblance of a relationship that didn’t include a dramatic exit followed by a hate text.   


I put on my biggest “tour guide” hat and I started making a plan for a memorable night on the town.  I thought about my favorite hidden gems in this city and I made reservations that would solidify a solid schedule of adventure and exploration.  It was as cathartic as writing this story because it caused me to really take a look at the places that defined me in this town.  I wasn’t the kind of girl to wait in line for a Hollywood Hotspot.  I was the kind of girl that knew the hotspots that had the flavor of LA without the line.  And as I continued to plan, Grey continued to prepare for the job that he was wholeheartedly pursuing.

He continued to read books on leadership to freshen up his interviewing jargon.  He continued to take care of himself by working out regularly and riding his bike through the mountainous landscape.  We continued to see each other regularly; often times with a bottle of wine and conversation on his couch that he shared with so many before me.  But one night, we started talking and it led to an interesting conversation.

“What do you desire?”, he said.

“What do you mean? What kind of desire? I have many…”, I responded.

“What kinds of sexual experiences have you always wanted to try but never felt you could?”, he said.

It was an interesting question and one that I hadn’t thought about in a long time.  I had done a lot of exploring of other men in the last few months and, outside of my experiences with Mr. Grey, they were pretty mechanical and stale.  I knew men.  I knew them well.  There wasn’t much that I hadn’t explored in that fashion.  So what did I desire that I never have or wanted to?

The next revelation comes at the risk of judgement and concern from you as a reader. 

It is something that I have thought long and hard and debated whether I wanted to talk about. 

But if this story is about being honest and telling a true and authentic story, I must be brave enough to talk about the parts that scare me. 

So here I go.

“I have always wanted to explore more in women”, I admitted; knowing that my words would not be met with concern or judgement but rather intrigue.

I thought his reaction would be like a kid in a candy store.  I thought he would push me to pursue this passion in a way to exploit me through his own wants and desires.  But just like he always did, he surprised me.

“Why don’t you date women?”, he said.

HIs question caught me off guard and created a tongue tied moment.  While I had experimented with women as a young adult, I became burned through the process.  In those experiences, I felt like I was being pushed to pursue something through someone else.  I was thrust into pre-meditated situations that were unbeknownst to me.  The exploration was never about me and what I desired; it was about the man and his desires and I was simply a piece of the puzzle.  And when the desire started to drift outside of my relationship with the man I dated as an early twenty-something, I ran.  I ran away from him and the opportunity to explore this part of me; deeming it “wrong”.  Even though I never considered myself very traditional when it came to sex, this experience made me tighten up my traditional belt and live a life that was acceptable to others. I ignored my innate desire and never mentioned it to anyone until this very moment with Grey.

“Do you think I should?, I said; it was a rhetorical question that I wasn’t asking him, but myself.

“Sure, why not?” he replied.  “How are you going to know what you like if you don’t try?”

This kind of “permission” was not something I was used to or experienced before.  Of course, Grey and I had given each other permission to date others because of the nature of our “Dating in the Grey” philosophy.  But I had never had a mature conversation about sex and desire with someone whom I felt truly comfortable and accepted.  Just as my support for him to potentially move away was selfless, his support in allowing me to discover the hidden parts of myself was also selfless.  And in this moment, I knew that he was and always would be someone special in my life.

After a brief second of thought, I couldn’t figure out a single reason why I shouldn’t try to go on a date with a woman.  What did I have to lose?  I had never done it before.  Hell, I don’t even know if I would like it.  But there was only one way to find out and I refuse to live my life with regret, even if the exploration scared the shit out of me.

I changed my dating profile so that my selection would only include women and I began swiping for potential date partners.  There were all kinds of women to choose from; women who were looking for another to join their partner, women that were tried and true lesbians and women who were seemingly straight but chose to include all genders in their search.  I knew that I wanted someone that had more experience than I; to show me the ropes if you will.  I was committed to being completely transparent about my situation and exploration and that was a roadblock for many women who were solely searching for their same gender.  I connected with a woman who I call “The Lesbian”.  She was one who was tried and true and she wasn’t very interested in pursuing much with me since I wasn’t tried and true myself.  I was honest with her; telling her that I had a male partner that I spent time with and who I recently had a conversation about my want to explore.  She pretty much told me to buzz off.  I could understand why; she was looking for something serious and I didn’t know what I was looking for and I wasn’t even sure if she would be an option.  I let the conversation die for a couple of days but then I asked her a question.

“How did you know you were gay?

It was a sincere question that I had asked myself in the days since Grey and I talked about desire.  I had always been attracted to women.  When I would watch videos that would turn me on, they consistently involved two women.  And while I had always dated men, did this make me gay?  What if the reason I had yet to find “my person” was because I never gave myself the opportunity to truly explore?

The Lesbian answered my question with a long explanation about how she also dated men during her youthful dating years but she always felt like something was “missing”.  It wasn’t until she had her first real relationship with another woman that she knew that the “missing” element was the X chromosome.  I wondered if I would feel the same thing.  I connected to her story and told her that I may be at a crossroads myself; but I didn’t have the experience to be able to truly test this theory.  Her tone changed and she started asking me a lot of questions; a characteristic that men didn’t typically encompass.

The Lesbian and I chatted for a while and we made a plan to grab a coffee when she came back from vacation.  We exchanged numbers and she began texting me photos from her adventures on a tropical island.  My responses were consistent yet short.  I rarely engaged much via text with anyone new.  I thought things were going great and I was killing the Lesbian game, but then she texted me,

“I do not think we are a good fit because of your waining communication”

Dumbfounded was the best way to describe my immediate reaction. I thought back to our short texting relationship. She would send me photos everyday and I would say things like “looks amazing” or “so fun”.  Since I didn’t know her and I hadn’t met her yet, I was holding back the vulnerable conversation until we met. But now, she was breaking up with me before we even got together.

This was truly putting the proverbial “shoe on the other foot”.  It was the first time in my life that I felt compassion for men.  Was this what dating a woman was like?  Were we really that “crazy”? I remembered every time I got in a heated argument with a man because he said “all women are crazy”. I also remembered every time I broke up with a guy because I didn’t like the emoji he replied with or the frequency of his texting or his grammar or his lack of syllables in his responses. I mean, if crazy meant having severely high expectations but never communicating what they are; than yes. I was today years old when I discovered that all women are crazy.

“What do I say?”, I asked myself. 

But then I realized that I know how to handle this.  I simply have to ask myself, “What would I want to hear?” You see, I had the advantage of being a women and I could relate to how she was feeling. She didn’t think I was interested in her and she was clearly very interested in me. This was a test to see if I was going to step up or step out. The truth was that I wanted to meet her and I didn’t want to be dumped so I apologized for the lack of attention and reassured her that I was still interested and looking forward to seeing her.  And then I let out a deep sigh because women are hard.

The next time I saw Grey, it was time to show him the city he had neglected his entire time here.  I didn’t tell him where we were going or what we were doing; he liked surprises just as much as I did.  Instead, I told him to dress up and to be ready at 5pm to be picked up by yours truly.

A memorable night is not just about the places you go but mostly about the company you keep. 

I had become great company for Mr. Grey over these last few months, but I wanted to feel strikingly beautiful on this occasion. 

I wanted him to look at me with those wild eyes like I was a slab of meat and he was starving. 

I knew just the dress that would create that effect; an olive green, backless dress that hugged my curves like a pair of Spanx. 

The strappy back and silkiness of the fabric required a complete commando interior. 

You could see my largest assets and could imagine the hidden gems, all tucked away behind a thin layer of material.

When I arrived to pick up Mr. Grey, I intentionally exited the car so he could take me in.

“Aren’t you a sight for sore eyes”, he said as he scooped me into his arms and kissed me with his firm lips; smacking my ass and squeezing it when I least expected it.

“Thank you. I thought you would like it”, I said with a sultry smile.

“I do.  Turn around and let me see you” he said as he stared.  I slowly turned around while keeping my gaze on his face as to not miss a moment of his response.

“You are beautiful”, he said and I blushed immediately. 

Grey was not the type of guy to give compliments often, but when he does, I soak them in because I know how special they are. 

We got in the car and I sensed a different energy in him.

“Are you excited for your night on the town?” I said.

His eyes had a special sparkle in them and his face lit up at the thought. “Hell yeah I am”

As we drove, I chatted with him about my conversations with the Lesbian.  Per usual, I had told him everything about her and so he was fully abreast of our interaction.

“The Lesbian says I am not texting her enough” I said

“Sounds like a woman to me”, he said with a smirk as I punched him playfully in the arm.

“I didn’t know how to respond to her, so I told her what she wanted to hear; what I would want to hear if I was her” I said. “What do you think? Was that a mistake?”

“As long as it was the truth, that is all that matters”, he said.  It was sound advice and I knew that I did the right thing by calming her fears and reiterating my excitement and interest.  Maybe I wasn’t failing at this Lesbian thing after all.

We drove down Sunset Boulevard as I verbalized all of the LA history I knew.  And when I ran out of my tour guide jargon, we arrived at the West Hollywood Hotel where our night was scheduled to begin. 

As I pulled through valet, I gathered my things and watched the shock and awe cover Mr. Grey’s face.  The exterior of the hotel was modern with clean lines and a group of upper class thirty-somethings gathered by the stream of cars that were coming and going. 

As the valet opened our doors, we stepped out and entered through the large doors that were almost too heavy to open.  a

The Lobby was like we stepped out of the real world and entered a movie where we were the stars.  Grey’s strut became slowed as he looked at the expansiveness of the hotel.  I pretended as if I owned the place and found my way to the concierge and let them know that we had arrived.

“Cufflinks” is all he said; a term that we created to describe anything that was classy and sophisticated.

“Ms. Lawrence, please follow me” instructed a man who looked like he just stepped off the cover of GQ.  The gates to the shiny elevator door opened as Mr. GQ chose the rooftop and scanned his exclusive entry card across the elevator panel.  As we stood alone in the mirrored walls of the elevator, we stepped back to take a look at us.  The man I saw in the reflection was different than the man I met months ago.  He was driven and focused.  He was handsome and refined.  He was “cufflinks”.

We were seated in a corner of the partially enclosed rooftop, next to the service station.  While I didn’t want to be a complete pain in the ass, this simply was not what I envisioned for our stereotypical Hollywood night.  While I could see the view of the city lights across the distance of the establishment, the bright lights and the constant banging on the ordering system was ruining the mood.

“I’ll be right back”, I said as I left him at our small, intrusive table in the corner.

As I walked back to the person who seated us, I was determined to get a table outside on the veranda, one of a few tables that allowed for privacy and a quintessential view of the Hollywood Hills that was only replicated on the big screen in movie theaters.

I walked back to the hostess stand and pleaded my case.

“I am so sorry to do this and I don’t want to seem like an ungrateful asshole.  But this is a special night for me and my man.  I really wanted to show him the beauty of this city since his time here may be limited.  Is there any way to move to one of the tables on the veranda?  I know you are busy but it would really mean a lot to me and to him”

Without a single hesitation, we were moved to the exact location I was hoping for. 

I tried my best to hide my enthusiasm but it was bubbling out of me like mentos in a coke bottle. 

Grey and I ordered some fancy cocktails and a few vegan dishes to munch on while we sat back in silence and took in the world around us.

“Isn’t this beautiful?” I asked, as if I was saying it to myself and to him.

“I have never seen anything like it”, he responded. The look on his face was more priceless than the view.

The next place we arrived was one of the hottest restaurants in LA.  I chose it because it had a busy vibe and a vegan menu that would impress Grey’s limited palette.  The entry to this restaurant was as familiar as the Hollywood sign; it was a place where Instagramers posed to show that they were bigger than their social network.  We walked through the tunnel of twinkle lights that were covered in greenery that was fueled by the sun and the open air of the entrance.  The clientele was a variety of Entertainment industry types, club goers and women who looked like they would star in the next edition of “Debbie Does Dallas”.  As slid into the large booth, Grey slid beside me; touching my leg with his hand and giving it a slight squeeze.

As we plowed through the plethora of food and drinks, I could sense a vibe that I had never experienced from Grey.  I didn’t want to dive into it in this busy restaurant and instead; insisted that he order dessert since they had options that would suit his plant based tastes.

As he took a bite of the pistachio pie we ordered, he leaned his head back in ecstasy.

  I knew that look but usually it came from private moments together; not in a restaurant full of people. 

I kept thinking about this new feeling I was sensing from him and I was eager to get to the root of it.

We made our way back to his place since it was the house that we shared so many of our most memorable moments.  He poured us each a nightcap and I didn’t have to do any prompting for him to reveal the new sensation I was picking up on.

“No one has ever done anything like that for me”, he said.

My head snapped to look at his face since I was taken back by his comment.  He was staring at me with grateful eyes that were full of tears.  In this moment, I knew what he meant.  He spent a lot of his time teaching others to live a life outside of boundaries; but little time receiving the same in return.  While my night was not inclusive of sexual deviant behavior; I had showed him life outside of the tiny little neighboring town that he spent all of his time.  I created a night that was all about HIS exploration. It was a special moment of utter vulnerability and I was showered in the “shiny pieces” of him as he stared at me with his grateful eyes.

When it came time for the Lesbian and I to have our first official coffee date, I was nervous.  To make matters worse, I had left my phone in the Uber the previous night so I had no way to confirm the date or know if she had cancelled.  The last thing I wanted to do was stand up the already tentative Lesbian but I had no idea where this coffee shop was and with no phone, I had no directions.  So I time travelled to 1997 and Map-quested the directions from my home computer.  I wrote them down on a sliver of paper and headed toward the coffee shop in hopes that she would show.

Even though I was honest about my stance, I still had no idea what I was doing or what this would feel like.  Was she going to “put the moves on me”?  How would I react?  The thought terrified me and aroused me.  What the hell was going on?

I arrived at the coffee shop and there was a line out the door. 

I walked up and down the sidewalk, trying to recognize her not so familiar face. 

This was a new experience.  I didn’t think about how women can camouflage themselves with makeup and flashy clothing. 

I thought I knew what she looked like but scanning the line, I was unsure.  But since no one looked at me with any recognition, I came to the conclusion that she was not there so I grabbed a spot in line. 

The line moved as slow as my texting and when I reached the spot where I had to decide what to order, I thought I was being stood up. 

She was considerably late and I was prepared to order a coffee for one.

“This must be what guys feel like”, I said to myself.

While I have never stood anyone up or have been stood up, I hear stories of such bad behavior frequently.  Maybe it was finally my turn.

As I was accepting my fate as a long overdue reject, I started pondering what kind of coffee drink I would order to drink my feelings away.  And just as I opened my mouth to order some sort of coffee milkshake, I saw a familiar face pop through the door.  It was the Lesbian. I breathed a big sigh of relief. Thank god she arrived and I wasn’t left standing solo, looking like a lost dog with a puppichino.  I ushered her to join me at the cashier and she ordered her coffee and I relinquished my original inclination for a milkshake and ordered an iced coffee and paid for both of our drinks.

“Definitely the dude in this relationship”, rang through my brain.

We found a quiet table and sat down.  My nervousness intensified with this newfound encounter and I did what I normally do when I am high strung; I talked incessantly.  I started with how I lost my phone in the Uber the night before and walked her through my morning of stress as I tried to figure out where to go without the safety of my connection to the digital world.  I confessed that I worried that she wasn’t gonna show up.  She calmly sat and listened to my unending blabbering and when I was finished, she started asking me questions.  She asked about my kids and the things I liked to do; it was refreshing for me to feel a sense of genuine interest in getting to know me.  I appreciated it so much and that is when my nervousness finally started to fade away and I really started to see her.  She didn’t look like a stereotypical lesbian, whatever that means.  She was blonde with long hair and a slender figure with curves.  She dressed casually with joggers and a tank top with some trendy high-tops.  I wouldn’t consider her “butchy” but more “sporty”.  She had a twinkle in her eyes when she looked at me which made me blush and she smiled often which I took as a compliment.

Now that I calmed down, I wanted to know more about her.  I asked her about her trip and what she did while on vacation.  She had an adventurous spirit and liked to explore new places and experiences; which was something we had in common.  The difference in my interaction with her and the experiences I had with men was the level of understanding between us.  There wasn’t an underlying mistrust in our interaction; but rather, an unspoken commonality that I didn’t know where it came from.

The conversation was easy and flowed, but I didn’t feel the same sense of intensity as I did with men.  There wasn’t the carnal intoxication of chemistry, even though I was attracted to her.  I was confused because it felt different and I didn’t know how to interpret my feelings.

When we finished our caffeinated beverages, I thanked her for meeting me and she was gracious for the free coffee. She began to stand up so I followed her lead and we made our way to the door.  I dragged behind as I approached the exit and started to feel like an elementary school boy, left wondering what to do next.  My nervousness returned with intensity and I was left fidgeting in my skin.  She stood there and watched me while I averted my eyes because I had no idea what to do.  Per usual, I rambled about having a great time and a bunch of other things I seem to have blacked out.  I gave her a quick hug and said goodbye and pretty much ran to my car as fast as I could.   

As I huffed and puffed from my sprint, I immediately called Grey.

“I had coffee with the Lesbian.” I said.

“How did it go?” He asked curiously.

“It was fun and weird all at once.   I thought she wasn’t going to show up cause she was severely late.  But once she got there, I think it went ok.  It felt like we were friends but I don’t know how to make the transition from friends to something more physical so I basically ran away”, I said. “It didn’t have the same feeling as I do with men.  It was totally different and I don’t know what to do with it”

“Of course you aren’t going to feel the same as you do with men.  She is a woman.  She is going to operate in a way that is foreign to you.” he said as if he was a self-help guide on “how to date a lesbian”.

I sat in silence for a second because his words were so obvious but true.  I can’t compare her to the men I dated because, obviously, she was not a man.  And she did feel foreign in the best way possible.

Later that day, the Lesbian texted me that she would like to take me on a “real date”.  I knew I had limited time to respond since I was already on dating restriction since she gave me the “waining communication” warning.

I felt more self assured now that I met her and had a better idea how to navigate this uncharted territory.  I quickly responded to the Lesbian with favor and agreed to go on a “real date”, and then I sat back and wondered what a real date with a Lesbian entailed.

The second date didn’t start as disastrous as the first.  I had my phone, I knew where to go and I was positive the Lesbian was going to show up.  My nervousness was replaced with excitement of the elusive “real date”.  Was she going to sweep me off my feet and show me the magic I had been missing my whole life?  Or were we destined to have more “girl talk” and be platonic besties?  Even though I had no idea how this date was going to pan out, I knew I had to keep an open mind and not let what felt comfortable shy me away from experiencing something new. And this was probably the most “new” thing I have tried in a very long time.

I decided to wear something seductive yet classy. After all, I felt sexy in my short skirt and black top and hopefully, it would help me transition our relationship into something that actually felt romantic.  I easily found the restaurant and checked in with the hostess who showed me to the waiting Lesbian.  She didn’t get up when I arrived and stayed seated while I slid into the booth.  She looked pretty with her hair down and makeup applied. She was still sporty but in a dressed up kind of way.  Our chit chat started and flowed easily as we ordered drinks and decided on a few appetizers to share.  We picked up where we left off and she shared more stories of adventures she has had throughout her life.

“I went to Costa Rica with my ex-girlfriend.  It was so amazing and beautiful.  I will show you pictures” and she scooted close to me so I could peer at her phone while she gave commentary about each location and photo.  I listened to her intently at first, but as I watched her scroll through the photos of her previous relationship, I began to focus on my own inner dialogue.

“What if that was you in those pictures” I thought to myself.  I tried to see myself traveling the world with this woman, holding hands with her and kissing her like the girl in the photo.  I didn’t feel any kind of jealousy or animosity seeing her with someone else.  That was surprising because if a man did this on a second date, I would think he was a giant douche.

“Man, I didn’t realize how much shit we give guys” as the gender comparison ran through my head.  My mind started down the rabbit hole of reminiscing every time I told a guy he wasn’t good enough or wasn’t performing up to my standards.  If anything, this experience has made me a lot more empathetic.

“You good?” Said the Lesbian and I snapped back to reality.

“Yep!” I responded, realizing my resting bitch face probably said otherwise.

I asked her questions about her life.  She was a veteran ER nurse who spent most of her career working the nightshift that caused her to become somewhat of a vampire.  In hopes of attaining some normalcy, she took a job pushing paperwork in an office.  She said it was super boring but at least she had a normal schedule.  I wondered how long that would last since boredom is the only ingredient needed for unhappiness.  I shared more about myself, telling her about my background and how I became a television producer.  The conversation flowed easily like the last time, but I was searching for some sort of chemistry between us.  I knew it wouldn’t feel the same as a man, but wouldn’t I feel something at all?

We finished our food and our drinks and the waitress brought our bill.

“would you like to split it? I asked.

“No, I got it” she said with a smile.

We walked outside and stood there awkwardly facing each other with giant smiles plastered on our faces.

“I parked over there”, she said.

“I’m over there”, I responded while I pointed to my car in the opposite direction.

“Thank you for a great night.  I had fun” I continued. I didn’t run away this time, but I turned into a deer in headlights.  Scared out of my mind but not moving a muscle.

The Lesbian leaned in and prepared myself for the moment I had been thinking about since we first said “hello”.  Her lips came closer and I could smell her newly washed hair.  I took a quick breathe in while I prepared for her touch. Her lips were soft.  Softer than anything I had ever felt.  It wasn’t a long kiss, more of a soft peck.  I opened my eyes and she smiled again and said “goodbye”, leaving me standing like a statue on the sidewalk.

As I made the long walk back to my car, I was anxiously trying to translate my feelings.  Did I feel magic when she kissed me?  Has my world been turned upside down?  Has this made me realize that I had been swimming in the wrong pool all along?

I kept asking myself, what do you feel?  I felt excited, anxious and mostly confused. I didn’t feel longing or regret.  I didn’t feel chemistry or revulsion.  It was like the experience did not touch any of the emotional parts of my being.  And that is when I knew.

I got in my car and I did what I always did, I called Grey.

“What’s up”, he said on the second ring.

“I am not a lesbian”, I said matter of factly.

Grey laughed at my non-sequester.  “Ok. How did you figure that out?” He said.

“She kissed me and I felt nothing.  I mean, I liked it.  She had soft lips and stuff.  But I didn’t feel any sexual desire or longing to be with her.  I should feel that, shouldn’t I?  I think I should”.  I took a deep breath and sat back into my car seat.

“Maybe she wasn’t the right girl.”, Grey said.

“I don’t know.  Maybe.  I just know that I don’t want to date her.  And honestly, I feel so bad for guys.  We give them so much hell.  I am definitely changing the way I operate when I date.  No more “you aren’t texting me enough” bullshit.  That fucking sucks”.

Just then, I got a text from the Lesbian. “It was nice seeing you again but I don’t think the chemistry is right between us”.

I felt the ping to my insides as I took in the rejection, but then I let out a huge sigh of relief.

“The Lesbian dumped me”, I said.

“Just now?” Replied Gray

“Yep, she texted me that the chemistry wasn’t right.  I feel like I have used that exact same line about 15 times.”

“I guess you are off the hook”, Grey said. I could tell he was smiling and trying not to laugh.

What an eye opening experience this has been.  These two dates with the Lesbian didn’t fully close the “do I like girls?” chapter, but what it did do was provide some pretty hard truth.  The fact of the matter is that dating a woman is hard because of the hidden expectations.  The expectations that aren’t communicated until you unknowingly fail at meeting them, at which point, you get chastised and possibly dumped.  And the hardest truth is that I was actively doing the exact same things that the Lesbian did to me; so much so, that it was almost plagiarizing my own experiences.  It really made me take a good look at myself and want to make a change.  I didn’t want to be the girl who made anyone feel “not good enough”.  I think I owed it to them to communicate my expectations so they will know how to meet them.  Or even better, I tried to have no expectations at all; so that everything is a surprise.  This experience didn’t give me the answer I was looking for, but it definitely changed me and it changed the way I want to date.

“So what are you doing now?”, he said.

“Nothing.  I was going to go home and chill.  Why?” I curiously asked.

“I have some news.  Why don’t you come over?”

I agreed and started to drive to his house when my mind started racing.  What was this “news”?  A list of scenarios ran though my head. “He has an STD.  He fell in love.  He wants to stop seeing me”. The proliferation didn’t stop until I walked through the door and said,

“Ok, what is the “news”?”

“Calm down, firecracker.  Just sit down.  I bought some wine.  Want some?” He said calmly, which was annoying.

I gave him a side eye but sat my ass down on the couch like a tantruming toddler, waiting for her punishment.

He was overly pleasant which was how I knew that something was wrong.  We talked about my date with the Lesbian some more but I couldn’t get the “news” out of my head and he was obviously waiting for the right time to tell me.

“Why don’t you just spit it out.  I can’t wait any longer.”, I said.

“I got the job.” He said.

“You got the job?” I repeated while letting the words sink into my brain.

“Yeah, they called me today.  They offered me a salary I couldn’t refuse, they are going to pay for my entire move and they want me to start ASAP”, he said with a guilty smile.

“Oh my god!!  That is amazing!!” I said as I jumped off the couch and gave him a big hug.  “Everything about this job has felt right from the beginning.  I knew you would get it.  I am so proud of you!”

“Thanks. I told you that job was mine”, he said with his boyish grin that I had come to love.

We cheers to his new beginning and as I took a large swig of wine, the reality started to sink in.  Grey was moving.  Not just moving down the street but moving six hours away.

My eyes started to well up with tears at the thought of him leaving my life.  In my mind, I thought was would make it to the six month mark and have the conversation about commitment.  But here we were, and that conversation would never happen because he was leaving and I couldn’t go with him.

While I chugged my wine, I thought of all of the times we spent together; the outdoor adventure that led to a surprise picnic on the top of a mountain, the third date where I insisted we go rollerskating, the crazy sex we had all over this house that will no longer be his home.  My eyes started to tear up as I chugged more wine.  I wasn’t ready for him to go.  I felt like I needed more time.  How was I supposed to say goodbye to someone who had become such a massive part of my life?

“So, what does that mean for us?, I said with baited breathe.

Chapter 10: The End










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Chapter 10: The End

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Chapter 8: The Verdict