What I Learned From Dating 53 People in 6 Months

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Dating is a numbers game. Any seasoned dater will tell you that if you meet as many people as possible, you’re eventually going to meet someone you are compatible with. It’s really easy in New York to never have to settle, to keep feeling like you could trade up. (That’s why I celebrated my having a crush for all of a hot second before I decided that I’m being stupid because crushes are irrational. Shush!) I’ve met people who have rosters filled to perfection, for whom seeking dates is a full time job. I even know someone whose SQL dating database was code named JEDI, short for Jon’s Enhanced Decision Index.

My Excel spreadsheet had a way more pedestrian name: ‘Dating spreadsheet’. I didn’t get terribly creative there.

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This spreadsheet is my life’s work. Nah, just kidding. It’s about six months worth of meticulously tracked data for all the dates I went on, and associated demographic information and a subjective rating of attractiveness. My impetus for keeping a record of the dates I’ve gone on was, of course, a break up. Data is manna for the heartbroken, analytical soul. I had been in a relationship for a year and a half, and our relationship was torn apart in December 2013 by immigration laws.

We had differing ambitions, as is often the catch when people in a relationship have a selfish goal in mind and are merely concerned with how to get it done (hover for explanation, click to read more) and not whether it is the right thing to do. Heartbroken, I decided to intellectualize – which is a neurotic, not a mature defense mechanism – to help me get over the disappointment. I told myself that even if I didn’t find love, at least I’d have a really rich data set that I can pore over and make a project out of.

Tangentially, my ex-boyfriend also had similar analytical leanings. He made an infographic using Javascript on how the frequency of conversation with different important people in his life ebbed and flowed over time – me included. (We did not brainstorm together, no.)

My first reaction to this graph was: who is dat beyotch who replaced me

My tool of choice was a little more plebeian. I am an Excel and Powerpoint junkie, so I organized my rows and columns into neat little pie charts and bar charts. Here’s a snapshot of my dating escapades – I stopped tracking in the middle of last year because I decided to see someone exclusively (which obviously didn’t turn out.) I stopped counting dates if they were no longer in the running for a relationship, which would happen after an open and honest discussion about our status or if we just never talked again.

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I found myself going out with people just because they fell into what I considered an attractive bucket (PhD, Ivy League, etc.) and may have had lower standards for other attributes (appearance, etc.). I found myself enjoying the social dance of first dates – being genuinely intrigued by people’s stories, being just sufficiently intriguing by dishing out an appropriate amount of vulnerability. I learned what people found attractive about me, and optimized by playing those attributes up. I learned how to get over rejection, and I learned how to let people down. I learned what I found important in a partner, I learned what my needs were in a relationship, and I learned that timing and feelings are such integral parts about dating, even though I wanted to do away with ambiguity by being as scientific about feelings as I could. All in all, it was a great learning experience, and a lot of my rambling philosophies about relationships and life and dating are borne out of this data set.

It wasn’t an easy experience. I worried about lacking a strong sense of identity, and what I was supposed to do about my number 1 project if I saw someone exclusively. When a guy and I would go past a certain number of dates, I would be told that my demeanor seemed too strategic, too calculated – I suppose it’s hard to seem genuine when everyone’s a data point in a data set. I’ve become very good at dating, but not in a positive way. It was at once thrilling but also dreary and just plain exhausting. I adored the attention but every once in a while felt depressed over the lack of something more meaningful. I fell for people who didn’t reciprocate my affection and I had to break some people’s hearts. Neither of those things feel good to do.

Nowadays, I have moments of temptation where I wish to reinstate my data set. Quantifying things is so fun. I also don’t meet new people with as much ferocity as I did before. (In case you were curious about the math, it averages out to meeting 8.3 new people and 20.2 dates a month.) But ultimately, I have decided that it’s really not conducive to establishing a more meaningful connection as it pigeonholes how you view people and how connections are supposed to progress. It’s depersonalizing and frankly, not in the spirit of dating to find love at all.

I do have some massive generalizations by profession, and I think it’ll be fun to share my thoughts. Note that exceptions to the rule exist, and I don’t nearly have statistical significance between groups to make solid findings. Also some people fall in multiple groups, so this list is neither mutually exclusive nor collectively exhaustive. (I hate non-MECE Buzzfeed and Thought Catalog lists, so I’m just giving you a heads up.)

1. Scientists (computer scientists, physicists, mathematicians, neuroscientists, etc.)

These folks tend to appreciate my analytical side, and wouldn’t blink at the discussion of my dating data set. In fact, they often indulge my mild obsession with it. They tend to be awkward with touch (either too timid or too aggressive), wear terrible clothes, and are eager to debrief the cause behind the demise of our courtship. They appreciate honest feedback a lot.

2. Doctors

They tend to be good at being empathetic, sometimes infuriatingly so because I want to know how they actually feel and not what they think is the kindest response to me. They tend to have a good touch (give good back rubs, etc.), more so the procedural physicians than the diagnostic ones. (Click to understand the difference) Sometimes they can be pedantic, mansplaining obvious shit.

3. Artists (musicians, designers, writers, etc.)

Artists can be so captivating in their visionary ideas and stylishly edgy/grungy/hipster clothing, but they are often narcissistic and full of their pie-in-the-sky notions of arts and culture and how art eventually communicates big ideas to society. I think art has aesthetic value but it’s a terribly inefficient medium to get political or philosophical messages across, and I don’t like preachy people who don’t operate scientifically.

4. Finance dudes

Guys who work in finance are probably the suavest of the lot. They move conversations along with ease, make decent bank for their age, tend to be well-travelled, are usually less attractive (they have an average attractiveness score of 3.5 out of 7, under-indexing the sample average of 4.4) but make up for it with expensive suits. They can also be aggressive and upset if they don’t get what they want.

5. Foreigners

I know, not a profession, but all foreigners love talking about the inanity of the imperial measurement system. It’s your ticket to on-the-spot bonding. Discussing accents and cultural differences also tend to be a hit with these folks. I should know because I’m a foreigner myself.

I’d be open to doing a Q&A about my experience if there’s sufficient interest, so feel free to leave a comment/reach out.

You may wonder if I worry that future romantic prospects may like me less if they find out about my data-collecting ways. I’d like to think that being a homegrown social scientist is too ingrained a facet of my personality and they’ll just have to accept and better yet, appreciate it.

1/30 Update: Stay tuned for a Part 2!

2/3 Update: Part 2 here!

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The Author

Singaporean in NYC, analyzing relationships with a boozy brownie in hand.

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