50 First Dates Conclusion

July 11, 2023

It has been exactly four years since I started embarking on this 50 First Dates adventure to help me to overcome my fear of romantic rejection and to better understand what I actually need out of a long-term romantic partner.

This experience has transformed one of my deepest fears into one of my greatest growth journeys. It has turned dating into such a positive, fun learning experience, instead of a scary, arduous one. I am so appreciative of that.

Wednesday, February 15, 2023

At the end of my last update, I was open to and hoping to have a relationship with someone who felt like my best friend and had the potential to be “the one.” I feel incredibly lucky that I was able to experience that. I got to go on well over 50 dates with the same person which was a wonderful learning experience in a wholly different way.

I also experienced a different kind of heartbreak- one in which I had no anger to shield me from fully feeling the depths of my sadness. Overall, I am incredibly thankful to have created singularly beautiful moments that I will cherish forever. I have found that simultaneously holding both the good and bad can be difficult to do, amplified by the dualistic thinking that has ruled much of my adolescence.

As I stated in my previous reflection, when you allow someone into your life intimately, your inner reality often gets reflected back to you, which includes the good, bad, and the ugly. I was faced with some hard truths about where I am in my own development journey. Many of my long-standing insecurities were brought to light and I was forced to confront them in ways that I had not before. Fortunately, my partner was able to create a space that felt safe for me to address these things head-on without fear of rejection for not coming from the perfect family or being the perfect partner. To his credit, our day-to-day felt magical, loving, and safe. For anyone who spent time with me during this period, they know that I could not stop raving about my partner at any given point. I wanted to share the love and security that I felt with the entire world. I was just so overjoyed that I finally was experiencing it. This relationship helped to fill a decade-long desire to have a whole and healthy love.

Unfortunately, I was also faced with an uncomfortable truth. Love alone is not enough to sustain a long term relationship. It’s just table stakes. You can love someone fully, but if your core values are perpendicular, it’s unlikely to work out for a long term relationship. I now know that to make a long term relationship work, it requires love + logistics.

One of my long standing fears after my first love was that I would never be able to experience that kind of all-encompassing reciprocal love again. Now I know it’s out there. I am confident I will be able to experience it again, even if it takes many years to find. And now that I better understand my non-negotiables, I will be able to walk away quicker when a relationship is not right for me, to leave space for the right relationship to flourish.

There are so many profound learnings I have gained as a result of this relationship. Here are some of the most prominent ones:

1. My life is already full of healthy, unconditional love. So many other types of love fulfill my need for love. My most recent breakup has so clearly shown me how lucky I am to have so many deep, loving friendships that show up for me when it matters the most.
2. I need to continue to heal my relationship with myself. I am still insecure about my worthiness of love in some ways. This is something new that was flagged to me- I still have unresolved identity issues around feeling inferior due to my race and socioeconomic background.
3. Being singularly nice and optimistic is not me. I want to be able to be fully authentic and not the palatable, polished version of me that I am often forced to present to the world. I want to be free to express the entire range of human emotion without guilt or shame.
4. Somewhat related, I should not default to people pleasing to smooth over issues. This relationship showed me the utmost importance of proactively confronting core issues earlier. Leaving things unaddressed manifested in major cognitive dissonance; when I let this dissonance fester, it would surface in even more intense ways.
5. It is incredibly unfair to look for a partner to play a predefined role in the narrative of your life.
6. Dating someone who has a narrowly scoped physical type is incompatible with my values. There is no real value judgment here as many people have an ideal type, which may not be something that they can control being attracted to. I am not comfortable with dating someone who has a clear pattern of having a physical or racial type. It makes me feel like I am playing the second act to someone I do not know. And that is unacceptable to me.
7. The cover up is almost always worse than the crime. Hiding things or withholding the whole truth from your partner out of fear of the consequences is still a lie and is far more damaging to building trust. That can be hard or impossible to recover once it is gone.
8. Everyone has a past and it is a good thing to learn from experience, but it is not a fit for me if a partner has not reflected deeply on what their past has taught them and how they are going to do things differently.
9. Love isn’t about possession. When you love someone, you want the best for them regardless of whether you get to be with them or not. I used to be really insecure by the prospect of my exes finding someone who was a better fit for them than me. Now I am genuinely really happy for them when I see that they are in loving relationships.
10. Big events and milestones (such as holidays, weddings, and birthdays) can be good forcing functions for you to reevaluate whether the person you are with is the right person for you to experience those milestones with.
11. I might still need to fully individuate: which is the process of fully becoming and understanding yourself. I still need to do some work on decoupling my personal values from the values of my family.
12. There are still things I need to do as a single person for myself before I am fully ready to commit to a long-term partner. I have made a list of what those things are and I am going to get to doing them immediately so I can be ready for my person when we cross paths.
13. Doing the right thing and hard thing are often the same thing. I have proven to myself that I continue to choose to do the hard but right thing, despite the pain it may cause in the immediate term. I would rather face the pain sooner than have it cause even more damaging long-term pain down the line.

Of course I am reluctant to feel the crushing pain of a wonderful thing ending, but as my friend Greg always says to me, if it didn’t hurt, it didn’t matter. This hurt, and it mattered. I want things to matter. I know I am someone who feels things very deeply and loves wholeheartedly, which often scares me because I know the devastating enormity of how it feels to sit with the loss of that love. I want to be brave when the time is right and open my heart back up.

As I said to my friends for most of the relationship, if this is not my person, it feels pretty darn close to how I want my relationship to feel with the person I end up with long term. Quite frankly, I am currently reticent to put myself out there again anytime soon. I want to give myself the grace to take all the time I need to fully heal from this experience and work on the things that were brought to my attention about my own self development. I want to be ready when I am with my next great love to make it work for the long haul.

I have determined the short list of things I know I need to do for myself before getting into a long-term relationship. I don’t want to live with regrets or unfulfilled desires to try things before I commit to someone and start building a life together. I’m going to start living more fully and checking those experiences off my list.

This next chapter, I will be much less focused on dating (even though this series is about dating). I will be focused on doing all the things I feel like I need to do to be the right person for when the right person enters my life. I am going to spend my time investing into a foundation that I know will never leave me. I am going to take myself on 50 solo dates to better get to know myself and do the things that bring me joy. I am going to work on my relationship with myself, my friends, and my family. I am excited to start this new chapter, fully embrace living on the west coast, and start fresh on my own terms.