50 First Dates

May 25, 2020

So it is week 11 of COVID quarantine and I have finally had enough time and emotional distance to write about my experiences with post-grad dating.

By the numbers, I went on 22 first dates, talked to 400 guys over 7 apps, screened too many others to count, and now I am here, done batch one of dating.

Because I barely dated in college, my intention was to see what was out there and to be more open to meeting different types of men. I tried to keep an open mind about background and age. The oldest guy I went on a date with was 39 and the youngest was 21.

I will only talk about what I learned in the aggregate to protect their anonymity, but these are the insights and lessons that I learned from this round of dating.

Pre Dating (Summer 2019)

I honestly took an entire month to catch up on sleep after graduating, but once I emerged from my hibernation, my friends encouraged me to download several dating apps which included Hinge, Bumble, Christian Mingle, Farmers Meet, Coffee Meets Bagel, The League, and Crossroads. I stayed off of Tinder. At first, I was not planning on meeting any of these guys in real life — I can only imagine it came from a place of fear (and perhaps stigma). I was planning on practicing “getting to know people online” without having the pressure of ever actually having to meet them face to face. That worked for a while. It was easy to be spacey and not check the apps regularly. It honestly felt like a video game to me. I found the experience of swiping and selecting people solely by physical attributes to be incredibly vapid and superficial, but the validation I received from it was intoxicating. In early July, my friends and I agreed that we would all challenge ourselves to go on one actual date before the end of summer. That sounded easy enough, right?

My First “First Date”

I was staying in the city with a friend for the Fourth of July weekend. I just happened to be awake for my 5 AM workout and matched with a guy who wanted to meet later that day. I was feeling bold and spontaneous. Also, I wanted to go on one date to get it out of the way, so I could fulfill my promise to my friends, so I said to myself, “Why the heck not, let’s do this.”

My first tip that this was not going to be a normal date was the fact that he wanted to meet up within 3 sentences exchanged. That in itself was not a red flag, but that in conjunction with everything that followed was.

I rearranged my plans to make our date at an underground hotel bar. I planned an hour to get from Soho to Bryant Park, which I figured would be more than enough time by Uber. It was not. I let him continuously know the status of my delayed ETA. Eventually, I couldn’t handle holding him up any longer and I hopped out of my Uber, ran through Time Square in the pouring rain, only to make it 28 minutes late.

When I finally arrived, looking like a drowned mess, he said if I had been exactly 30 minutes late, he would have left. Off to a great start.

Over the course of the date, he asked what my salary and GPA were, as well as if I was still a virgin. After his super invasive line of questioning, he didn’t fail to mention several times that he was a managing director at a very big important bank. He even went so far as to ask if I wanted a job at his bank. I made it very clear that I did not. When we were leaving, he also made a joke about being 11 years older than me, which was super unnecessary and uncomfortable. He also asked if I was open to doing long distance. I was not.

Transition to 50 First Dates

I figured things couldn’t possibly get any worse than that. I also figured I had nothing to lose and only better experiences to gain. Ultimately I only went on dates for 4 months total.

As my sister likes to say, “sis snapped” and I decided that I want to meet a lot of new people and have new experiences, and learn about different perspectives. I’m not sure how I landed on 50 first dates, but I figured that it was a good number of dates to give me a good sense of what kind of men were there outside of the gates of Princeton.

Highlights

Here are of the most fun dates and memorable moments:

Learned how to ride a motorcycle. Minigolf. Top Golf. Getting featured on the jumbotron at my first Flyer’s game. Learning about the foster care system. Buying food for the homeless. Ax throwing. Live music at the art museum. Leaving a date early to take a solo nap. Freestyle bowling. Having a guy from SF fly out to meet me for our first date. Grown-up arcade games (okay not sure if they were actually for adults). Listening to people’s life stories.

Lessons

I learned about what boundaries are healthy and reasonable to expect. I also learned more about myself than I had expected.

1. I need to fundamentally like myself before I can like anyone else. I need to resolve my own insecurities (which I am now working on in therapy). I can not and should not look to someone else to validate me.
2. I need to learn how to live in the gray. Not everything is going to always be clear. There can be beauty in the in-between. I still believe that expectations should be clearly communicated, but not everything has to be planned out.
3. This goes along with #2. I am allowed to date without it being for the sole and explicit purpose of ending in marriage. Due to my fundamentalist Christian upbringing, I was conditioned to believe that dating should only be for the purpose of marriage. That put a lot of unnecessary pressure on my relationships from the very beginning. If I didn’t think someone had the potential to be my long term life partner within the first month of knowing each other, I was out.
4. Shared values matter more than anything else. Shared interests are important as well, but if your core fundamental beliefs aren’t compatible, it will be very hard to build from that foundation.
5. I can be cool until I care. Which really hasn’t worked out too well for me thus far. I am the most chill version of myself when I am not interested in someone, but once I do care, historically I haven’t been able to manage the flood of my emotions and somehow end up hitting the self destruct button to avoid greater intimacy. I am also working on overcoming this through therapy.

The last guy I was talking to had a profound effect on me. Being with him prompted me to make some necessary adjustments in my life including prompting me to finally sign up for therapy. Some lessons I learned from him were:

1. Speak my truth upfront: be myself fully from the jump and not put on any pretenses
2. Address issues, talk about them and then LET THEM GO
3. My over planning tendencies may not be healthy in all contexts

Other Mini-Takeaways

• Got over my pre-date barf syndrome (after date #8).
• Met an awesome triathlon coach and friend.
• Realized that in the process of getting to know so many new people, I forgot that I was someone worth getting to know.

Addendum August 12, 2020

I am currently getting to know a man who has the most direct and clear communication I have ever experienced. I am never left in the dark wondering how he feels about me or where we stand.

Regardless of where this goes, I know I am presently able to be my full self and be accepted for that. We are also aligned on the most important things. It seems like we are willing to grow together.

Ultimately I want to be with someone who doesn’t judge me for my idiosyncrasies and sees me for me. Rough edges and all.

It’s not about the grand gestures of love, but the daily steadfastness of someone looking at you and accepting and loving you for everything you are.

I recognize that by sharing so vulnerably, I open myself up to criticism, but it’s a risk I am willing to take and a tradeoff I am willing to make if it will help someone else to feel heard.

Addendum October 22, 2020

Even though the above guy and I were ultimately not the right fit for each other, I am super thankful for how he motivated me to get serious about thinking about and planning for the foundations of a solid future. I also learned an incredible amount about what I want and need in a relationship and how to communicate that clearly. I appreciated being able to practice healthy boundary setting. I feel confident going forward that I have sufficiently put in the work to address most of my past unhealthy habits, mindsets, and behaviors that are associated with an anxious-avoidant attachment style through therapy and will be able to maintain a healthy, non-codependent relationship with someone I love.

I am finally open to finding a real relationship, instead of shopping around for arm candy. I look forward to someday dating someone who is truly my best friend.