50 First Dates Revisited

April 16, 2022

I have spent the greater part of this past year trying to write my follow up to my first 50 First Dates update. I think things tend to write themselves at the right time.

It has been nearly two years since I first wrote V1 and turned my experiences into a framework for how I should approach dating in the future. Again, I will describe my experiences and learnings in the aggregate to best protect the anonymity of the people involved. I have dated in three cities on two separate coasts. By the numbers, I was in one committed relationship, experienced one reciprocated love, and grieved too many half baked situationships to count.

I think one of the saddest realizations I have had about adulthood is that you can love someone but not be with them, and you can be with someone but not love them. That was and still is a hard pill for me to swallow.

I am proud of myself in many ways. I opened up my heart and experienced some of the most beautiful, magical things that one can feel. I felt alive and finally understood why people like to sing about love so much. For the first time in a very long time, I did not have to frantically Google whether what I was feeling was love. I just knew.

Opening up my heart also came with some unintended consequences. For the first time since high school, I experienced the physical manifestation of my emotional pain through intense chest pains that lasted for weeks.

Since experiencing my first love, I have spent a lot of time and effort insulating my heart, making sure I would never again have to feel the utter devastation I felt back then. Quite frankly it took me multiple years to completely recover from my first love. My heart was not fully available for most of college. It was hard to let go of the hope that maybe in a future time when we were both older, more mature, and circumstances were different, that things would somehow find a way to work. Learning how to properly grieve the ending of relationships and to fully let go has been something I have practiced a lot over the last few years.

I am someone who likes to mitigate risk. I optimize for minimizing pain. I anticipate it and try to make it go away before it even has a chance to exist. Or at least, I have historically done this over the past two years. I realize that all of my frameworks on evaluating relationship fit and data points, while helpful, are all part of an effort to control the risk of being hurt by romantic relationships. I figured that with better data I could make better decisions in choosing who to love. I am realizing that while patterns and trends can help to inform healthier gut reactions and weed out bad actors, it cannot account for serendipity.

These are some of my biggest takeaways from my last 2 years of dating:

1. Be upfront and proactive about communicating what I feel when I feel it
2. I am learning to love people where they are at. You can’t enter a relationship wanting to change someone. I am learning this about my friendships too.
3. Practicing self compassion: When I am hard on myself it inevitably comes out reflected through me also being hard on my partner. I am working on fuller self acceptance. I will always want to be someone who continuously improves, but I also need to accept where I am in the process currently and be able to accept that person too.
4. Every time I date someone new, it gives me a glimpse into where I’m at currently. It is a almost a forced reflection of my inner emotional reality
5. I’ve learned what the nuanced difference is between a relationship that has romantic chemistry, and a friendship that has added physical chemistry but lacks romantic relationship potential.
6. Not to maximize for optionality. My perfectionistic tendencies have often prevented me from recognizing when I have something really special, even if it’s not perfect. It is okay to commit to exploring something exclusively when I am 85% sure about someone. I will never be able to get 100% if I am always open to finding the next best option.
7. Love is likely not going to happen in the timing I want it to, or the most convenient timing to fit into my life plans
8. Being perfect is not a prerequisite for being in a relationship
9. I can survive breakups and they won’t completely ruin me
10. When you love someone, you want the best for them even if that means that you don’t get to be with them. Love is not about possession — it’s about wanting the best for them regardless if you get to be a part of that or not.

None of this is revolutionary. You can google all of my learnings on pretty much any site that talks about love. In fact, I’m pretty sure I did before I started on this dating adventure. But the hard earned experience is something I am really glad I opened myself up to.

I feel so lucky to have gotten to know some really incredible individuals. I also feel lucky to have avoided some really bad fits. I feel extremely lucky to have learned so much about myself through this process.

Some Experiences That I Will Hold in My Heart

Dancing in the living room, picnics in Rittenhouse, exploring new neighborhoods, hikes in the snow, museums, seeing Ben Simmons at dinner, ice skating, skateboarding, lots of city skylines, dying on the Rocky Steps after biking around the city and having to hop the train tracks, lots of rock climbing, being helped with building my furniture (thank you), DIY pizza nights, spontaneous lunch time dates, basketball 2.0, surfing, symphonies, and of course meeting my sister and the people I love most.

My Approach Now

I believe it is most pragmatic to be dispassionate about dating, while remaining passionate about love. What that functionally means is that I’m just a little smarter about not jumping in both feet first every time I feel something stir in my soul quickly. I want to fall in love slowly. I know that’s not always possible, but I don’t want to confuse intensity for compatibility.

I thoroughly enjoy my own company now. Dating will no longer be my main extracurricular. I am excited about investing in my hobbies and deeply giving back to my community. I am excited to feel rooted in friendships that challenge me and bring me joy again. It doesn’t feel like I am looking to fill a void. Rather dating feels like a nice added bonus to an already abundant life. My life feels full.

I took a pretty long forced pause from putting myself out there. I gained a lot of clarity about what I want and need. I also was able to have the space to deal with some pretty difficult life stuff that I was distracting myself from dealing with by going on fun dates.

This summer I am looking forward to creating fun memories with friends in a new city and on a new coast. I plan on going on plenty of fun speed dating events and double dates with Nina. I’m excited to have the chance to meet people in real life again. I am excited to be able to be more intuitive about what feels right in my gut instead of being so checklist-y about things. I think online dating gave me far too much optionality. It certainly didn’t help me to curb my overthinking and analysis paralysis. I am also much less fearful of rejection and breakups.

I still hold that I would love to be in love with my best friend and be working towards a shared vision of the impact we want to have. I hope I get to be so lucky to find someone who is on a parallel journey to walk through this life together.

I am open to finding that person, but I am no longer in any rush to find that person in any clear timeframe. I hope with my next update I can share about what that is like.