50 First Dates: The Final Five

journey of self-discovery


“When I discover who I am, I’ll be free.” — Ralph Ellison, Invisible Man.

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Judgement & My Journey of Self-Discovery


I’m aware that I have taken a slightly unorthodox approach to reentering the dating world, however it is still so funny to me how differently people respond upon hearing about what I’ve done. Sometimes I’m met with excitement, and the other person has a million questions and is absolutely delighted to hear about my journey. Other times I’m met with disbelief; how and why would I willingly subject myself to the awfulness of a first date so many times?

I’ve been met with judgment and condemnation for turning dating into a “social experiment”. I’ve had the assumption made that I must be sleeping with everyone that I go out with. I’ve even had people become competitive with me and try to simulate what I’m doing. The act of being transparent with others comes with the inherent risk of opening ourselves up to feedback, opinions, questions, comments, and concerns. It requires a certain level of confidence in myself to be able to first go against the traditional dating model, and secondly listen to opinions about my actions without allowing it to distract or deter me from what I set out to do.   

Although it’s been an amazing opportunity for me to openly and authentically share my journey and story with other’s, at the heart of it all, this is still my journey of self-discovery post-divorce. I try to remind people that while I appreciate their opinions, ultimately for this to be a growing opportunity, I must remain autonomous and continue down my own path.

In the midst of my divorce, I remember feeling overwhelmingly lost, confused, and alone. During this dark period of inward searching, I read a quote that started me down my long, convoluted and twisted path:

“When I discover who I am, I’ll be free.” — Ralph Ellison, Invisible Man.



Stories About the Journey of Self-Discovery: A Common Thread


It’s fascinating to me that storytellers from every generation and culture have different variations of tales about how to discover who you are and become it. Whether a Greek demigod in search of his parentage, an Egyptian prophet called to lead a people, or a prince who longs to discover his destiny; they all give hints about what a person might have to conquer and how to master the challenges that occur during the path of self-discovery.

A common thread I noticed among these stories of self-discovery is that they all began with a series of questions. The characters were attempting to ask hard questions to find out who they are and how to be that person. Now granted at the age of 35, I felt that I had already answered many of the big questions pertaining to my own identity, however, I had absolutely no idea who I really was sexually or as a partner in a healthy romantic relationship.

Cue the the list of questions:

  • How can I be a single mom and date?
  • What do I want out of a relationship?
  • What do I like and dislike sexually?
  • What is my “type”?
  • What is my sexual orientation?
  • How do I want to communicate with a partner?
  • How honest and vulnerable do I want to be?
  • Is monogamy important to me?
  • How can I be what my partner needs without losing myself again?
  • what am I willing to compromise on and what am I not?

What a Journey of Self-Discovery Is & Is Not


I have made two lists because we all know how much I love them! The first list is what I think a journey of self-discovery is, and the second is a list of what it is not.

What a journey of self-discovery is:

  • The natural progression of a person’s self-discovery as they grow in understanding of life, the world, relationships, and self.
  • It is an intentional lifestyle of growing deeper in knowledge and wisdom.
  • The process of discovering one’s potential, values and beliefs, character, and motivations.
  • At the heart of a journey is the understanding that it is a journey. None of us are perfect. Once we start, we are not expected to achieve instant maturity. Rather, the purpose of living a life of intention is allowing it to become a lifestyle with daily practices that strengthen our commitment and awareness.
  • The process of learning how to set intentions and letting go of expectations of others to fulfill us, and instead looking within for answers.
  • Identifying and releasing limiting believes and fears that are no longer serving us.
  • Getting in touch with and learning to accept and cope with real emotions.
  • Recognizing your strengths, forgiving yourself, clarifying core values, finding what inspires you, spending time alone, and journaling.

What a journey of self-discovery isn’t:

  • It is not about proving a point.
  • It is not about abandoning everything that makes up who you are and completely changing into someone else.
  • It is not about anyone else.
  • It is not an overnight, quick fix or solution.
  • It is not easy.
  • It is not something that someone else can do for you.
  • It is not about playing small and accepting the status quo.
  • It is not something that can be unknown or undone.

Somewhere along the line, my journey was no longer just about me and my sexuality. I discovered that I genuinely desired a deep connection with someone that I could love fully and be loved by. However, I had absolutely no desire to look for this other person. Let me repeat that, I have no desire to search for my person.

journey of self-discovery

My Journey Led to Me


I discovered that instead of searching for the right person, I wanted to be the right person. I wanted my journey to help me fully discover who I am and how I want to show up in my relationships. My self-discovery led me to be motivated to be the very best me that I can, so that in turn, I will be able to fully love myself and freely give to another.

My journey was about learning how to identify and meet my own needs, so that the desperation of needing someone else to fill in the gaps for me, no longer existed. Focusing on learning how to be more authentic, honest, open, vulnerable, sexual, creative, bold, fearless, and loving with other humans, has enabled me to become a better version of myself. My journey of self-discovery has become a quest for self-love, and self-validation regardless of what’s going on around me. It’s been a journey of finding my voice and honoring my wants and needs. And, a journey of not just accepting my flaws, shortcomings, and imperfections, but loving them. It’s become a lifestyle of always seeking, growing, leaning in, and trusting. Living the messy ups and downs of being authentic.

I can’t believe it’s done… I DID IT!!!

journey of self-discovery

The Final 5. I Did It!


I went on 50 first dates in 4 months and learned so much about life, love, intimacy, connection, attachment, relationships, communication, sexuality, vulnerability, authenticity, bravery, humility, value and belief systems, and friendship. I have absolutely no clue what’s next for me, but I’m completely thrilled and ready to continue to meet life head-on as a woman rooted in sovereignty, who knows her worth and is unapologetically authentic!

journey of self-discovery

Date 46: Chuckles with Chuck


Synopsis: Chuck is a very cool, smart, laid back single father of two. A recent divorcee with a very clear live and let live vibe that was totally working for me. He is handsome, slightly introverted, dark-haired, clean cut, professional kinda guy. Ridiculously smart with a fresh perspective and super quirky sense of humor that inspires a constant smirk from his companions.

Yelp review: We had dinner at my favorite Thai restaurant, which happened to be in the same building as his office. Our conversations were all over the map and such fun. We discussed topics that had me intrigued, engaged, laughing, and eager to see what would come up next. Not once did I feel compelled to check my phone or find my mind wandering. I loved how funny his stories were and how real he was. He had a great balance of asking questions and sharing stories.

After our two-hour meal, we walked over to his office where we sat cozied up on the couch to watch the snow fall and drunken passerby’s stumble. We continued to engage in endless conversations with topics all over the map. I loved that he had so many new ideas to introduce and spar with, it was incredibly attractive to me. He invited me back to his house, and even though I was very attracted to him, I didn’t feel eager to take that next step. Overall I would give Chuckles with Chuck:

4 Stars⭐️ ⭐️ ⭐️ ⭐️

What I learned about myself: Connection, attraction, chemistry, and raw sex appeal are all still a little bit elusive in my very concrete mind’s ability to understand, as I have learned they are fluid. Fluid in a way that I’m striving to adopt and be. We certainly had sexual chemistry and couldn’t wait to take each other clothes off, but for some reason, I felt very nervous. I felt hesitant to ruin a cool connection with a lack of sexual compatibility. This was a hard one for me because although Chuck is an attractive guy, who is very sex-positive, I felt an odd suspicion that we may lack compatibility.

Normally I would rather find out sooner than later, but was hoping that I was wrong and that by taking things a little slower, we could build on our attraction… like a really long session of foreplay. Ultimately when we did end up sleeping together it fell flat, and we didn’t have enough between us to even motivate me to keep a friendship going. I didn’t feel sad or regretful, only left wondering why I can’t be in control of who I feel that spark with and who I don’t. If I had control, I would have loved to have off the chart chemistry with such an amazing, grounded, fantastic man. But such is life.

journey of self-discovery

Date: 47 Kurt the pilot


Synopsis:  Slightly tall, attractive, arrogant, and annoying. From the moment he sat down to dinner, I could tell that Kurt thought he was very important. When he got done talking about being a pilot, he switched to his next favorite topic: HIM.

Yelp review: We met at a restaurant that I don’t really care for, as Kurt was very adamant that it be where we met. There were not any vegetarian items on the menu, and he could have cared less. He was not only a person who loved the sound of his own voice, but also a person who had very little of interest to share. It was a very long meal. Overall I would give Kurt the pilot:

1 Star ⭐️

What I learned about myself: I was able to brush up on my skills in engaging in conversation with any person, no matter how drab. I also learned that I have fully mastered the ability to comfortably decline a goodnight kiss as well as to respectfully let a man know that I appreciated his time but am not interested in a second date. He handled that well, and we both went our separate ways.

It is great to have a mindset going into life now, that I am absolutely ok with not liking every person I go out with or meet. On the flip side, I don’t always have to be liked or well received by everyone either, and that it is in no way rejection or diminishing of my self-worth.

journey of Self-discovery

Date: 48 Creepy Carl


Synopsis: A 45-year-old chef who was seemingly average in every way. Very nondescript in appearance, mannerisms, and dress. Carl is the kind of guy who would never warrant a second look. He lacked self-confidence, exuded nervous energy, and gave off a vibe of desperation so thick it nearly had a scent.

Yelp review: We met downtown for a quick drink, where I quickly realized that it was going to be a very long night for me. Carl did not look very much like his picture and was not at all the funny chatty guy I had been messaging.

After a drink, he asked if I’d like to walk down the street to play pool, and I agreed. Things quickly unraveled from there. He had had his phone out much of the night, and although it seemed a little bit rude, I also didn’t really care. I assumed that he was texting. It was odd though, the way he was holding his phone, and how he would pull it out each time I was turned or had my back to him.

Something felt off about the exchange and eventually, I decided to move and get a better look at what he was doing. I quickly discovered that he had been taking pictures of me, and was texting my picture to other people. At this point, I was very uncomfortable and told him that I didn’t like it and was leaving. I grabbed my stuff and walked out.

It gets worse. He followed me out and was shouting at me to wait and hear him out. “I’m not a creep I swear, will you just stop and let me explain” And then, “There is no reason for you to be such a bitch about this”.

I finally stopped, turned around and calmly let him know that an explanation wasn’t required and that I just wanted him to stop following me. I let him know that he was making me feel very unsafe and that I wanted him to leave me alone. And then, even though I didn’t think it was possible, it got worse! He proceeded to tell me that the reason he had been taking my picture was that I look just like his dead sister.

At this point, I was wondering how in the hell it hadn’t crossed his mind that admitting to seeking out a date and attempting to take a woman to bed who looks like his dead sister is not a relief, but a whole new kind of disgustingly creepy. I got in my car and he stood behind me thinking that it would keep me from backing up. I told him to get out of the way or would call the police after I ran him over. I backed up and he moved out of the way.

I unmatched him, flagged his account, and blocked him. Overall I would give Creepy Carl:

0 Stars

What I learned about myself: This was a rough night for me, and I actually felt really scared about my safety and well being. I ended up making an illegal turn and got pulled over by a police officer. When I explained my night to him and why I was so upset, he was really cool and stayed with me until someone could come to get me. He didn’t want me to go home or be alone and told me that he has dealt with some crazy stuff pertaining to online dating and reminded me of how dangerous it can be.

Sometimes living in the small little town that I do, I have an illusion that I am safe. Safety is not something that anyone is guaranteed when dealing with unknown individuals. This was a good reminder of why I always text my location to a friend, including a screenshot of who I am going to be with. I also text that same person to check in when my date is over. Even with the safety precautions that I have taken, it’s still important to be careful, and follow my gut when something feels off.

journey of self-discovery

Date 49: Hard lines with Heather


Synopsis: Tall, athletic, long beautiful dark hair and a face that women yearn for in its symmetric perfection, make Heather absolutely stunning. She’s a soft-spoken, lovely, bold woman with loads of charisma. Wicked-smart and funny, she has a killer vibe of a badass chick who knows what she wants and how to get it. Being very driven, fiercely independent and outspoken, make her a force to be reckoned with.

Yelp review: Heather suggested that we soak at the Turkish bath house downtown, to which I eagerly agreed to. We met, and quickly found we had no problem finding things to discuss and laugh about. It became a race of who could get the next sentence in first with overflowing sexual innuendo and cheeky sultry looks. Not only were we enjoying witty, flirtatious conversation, but it didn’t hurt that we were both half-naked in a beautiful tiled bath house with snow lightly falling from the open roof.

We ended up having the place to ourselves for almost 20-minutes where kissing and touching became the most important order of business. After our lovely time together, we parted ways and I soon after received a very honest text where Heather let me know that she had a lovely time, but couldn’t date me again until I figured out what I wanted and was ready for a monogamous relationship. The way in which she delivered the text was respectful, honest, and fair, which only made her more impressive in my book. Overall I would give Hard lines with Heather:

4 Stars ⭐️ ⭐️ ⭐️ ⭐️

What I learned about myself: It’s complicated having a very personal journey of self-discovery that requires other people. It creates this odd dynamic of needing others to continue learning but also learning very individual life lessons. Something that Heather said in her text was. “I won’t be part of a string of broken hearts taken out during your journey of self-exploration. Thank you for sharing your beautiful self with me today, but until you are ready to belong to one person, I can’t even consider seeing you again.”

I had this profound moment of self-reflection where I had to ask myself if I still feel ok with what I’m doing. Is being honest and upfront with anyone I encounter enough to excuse the fact that I’m still entangling with very fragile human emotions?  Am I using other people to have experiences? Is that what we are all doing?Am I just a little bit more clear about my intentions with a more focused outcome?

How is what I’m doing any different from every other person who is hoping to meet someone with the expectation of either sex, connection, a partner, spouse, fuck buddy, etc? Don’t we all want something from others, especially in the dating arena? I think what struck a chord was the part where Heather implied that I have hurt other people with my inability to be exclusive.

My intention has never been to hurt or disappoint anyone, however, I am also very certain that this process was extremely necessary for my personal development. I didn’t want to get into a rebound relationship simply because dating sucks, being single is hard and uncomfortable, and I didn’t know what I really wanted. I knew that I needed an opportunity to see what was out there, what I wanted, how to find my voice, gain experience and knowledge that would allow me to show up more authentically in a relationship when I am ready.

So while I won’t apologize for doing what I needed to do for me, I certainly would apologize fully and genuinely to any person who felt hurt or rejected. The way we treat other people isn’t a reflection of them, it’s a reflection of ourselves, so I’ve definitely been mindful of how I treat those I engage with.

journey of self-discovery

Date 50: Ned The drunk


Synopsis: Dark hair, dark eyes, and dark circles under his eyes give Ned the appearance of a man who could use a home cooked meal and a full night of sleep. It’s difficult to ascertain whether or not he is intelligent as most of his words are slurred. Quick to dole out surface compliments, and easy smiles could give him an illusion of charm…if one is easily impressed.

Yelp review: I texted Ned to let him know that I would be about 15 minutes late to our dream destination of a dive bar that he insisted on. Upon getting there it was very apparent that he had been there for a while and was not interested in waiting for me to start putting the drinks away. I was less than impressed to see that my date was fully drunk, but being the super responsible adult that I am, decided promptly that the best way to fix the situation was to match his level of inebriation.

In my mind, this made sense. I mean I couldn’t ask him to be less drunk, but I could get to his level with just two well-made drinks at this particular establishment. I guess that Drunk Ned was feeling very charming and kept getting closer and closer to me and telling how beautiful I am and all about the things that he wanted to do to me. I had a moment of clarity where I decided that I most certainly didn’t belong where I was, so I phoned a friend and left. Overall I would give Ned the drunk:

0 Stars

What I learned about myself: It’s so funny how I started out 50 first dates as a non-drinker and ended my last date completely shit faced.

I started out this process with so many rigid ideas, beliefs/values, and limited experience in dating, sex, and romantic relationships. I think my identity started out as a way to feel safe with my brain creating order from the chaos of just trying to be a person. I made rules about how I would conduct myself in an attempt to understand and occupy my place in a world that often confused and overwhelmed me. I became me built on rules and limited understanding.

In my world there was ME and NOT ME and those were parameters that I could safely navigate. At first, I needed this rigid structure to feel safe, but as I’ve grown and evolved, I realized that these limiting beliefs of what is ME actually started contributing to my suffering. I was limiting my possibilities and putting myself in a tiny little box and had traded living authentically for the fallacy of safety.


journey of self discovery

50 First Dates: To The End & New Beginnings


Dear ones, safety is a fucking fallacy in life. IT DOESN’T EXIST. Life is unpredictable, messy, and fucking gorgeous. When I dared to stop and ask the hard questions of whether or not I was being my best self, whether or not I was living the life I truly wanted on my terms and in a way that felt good and was willing to honestly dig deep and get real with myself, I was amazed with what I found.

I think we are all so much more capable than we know or could ever imagine prior to taking a journey of self-discovery. If we find that continuing to wear the identity that we are currently wearing no longer feels good, but that we continue to do it because it’s easier than finding a replacement, and it grants us a false sense of security, that’s totally ok. I now know that when we are ready to try something new and step out of what’s been comfortable, regardless of whether or not it’s in our highest interest, there is a whole beautiful life of experiences and adventure that we deserve.

I believe that we all deserve to be the very best versions of ourselves and to fully know and love every part of us that exists. I’m grateful for the unexpected turns that my life took, for the unraveling of a marriage that wasn’t meant for me, and for the life that I had outgrown falling apart beneath me. They sent me down a path that made knowing and loving myself fully a priority!

Thank you for following along on my journey of self-love and discovery!

Cheers, K      


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