What I Learned From Dating 53 People in 6 Months – Part 2

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Now that you’ve gotten a teaser of my dating escapades in Part 1 of What I Learned From Dating 53 People in 6 Months, you didn’t think I was going to just leave you with a dinky chart of demographics, some groundless sweeping statements about professions, and not deep dive into the data, did you? I can’t possibly leave you hanging like that. I would love nothing more than to geek out about my methodology and the data-backed findings I’ve gathered.


Time frame

The first date in my spreadsheet was on December 11, 2013, and the last date was on June 14, 2014. There were altogether 53 individuals and 121 dates. All dates tracked were in the running for a relationship. In other words, former flames revisited are excluded, as are dates that explicitly had no forward trajectory.

Sample recruitment

I primarily met people through OkCupid. I enjoyed the wealth of information profiles provide, and being a data-driven geek, I put a lot of stock in the match percentage.


99% match, 0% enemy?! Of course imma hit that

Most of my online dates were from OkCupid, although I did join JDate for a couple of months and met approximately three people off there. (I will elaborate on this later.) There were some organic dates too, with meeting 3 out of the 53 people offline.

I was on Tinder for three days before I decided I hated it because it felt too much like a meat market – how do I decide who to respond to when opening messages are so generic? I’ve been spoiled by receiving long epistles on OkCupid, since it usually suggests thoughtfulness and deliberation – which Tinder is not built for. I talked with Asher, founder of Mesh, an online dating site poised to improve upon OkCupid. He believes that Tinder favors “chatty” guys, since the best way to impress yourself upon someone in the crowded Tinder space is to check in with them frequently. However, Tinder conversations are more a function of two people being down to clown in the next 24 hours than any real indicator of compatibility.

I did begin to use Tinder in the past few months, after I ceased updating my spreadsheet. I wanted to treat dating as a more organic process than trying to analyze profile verbiage and messages. I was consciously trying to leave the fate of my dates to greater randomness. The people whom I’ve met on Tinder are people I’d probably discount on OkCupid. Like my current crush whom I met on Tinder, who purportedly hates talking about himself but beneath his reticent demeanor lies a sweetheart. *gush*

Establishing dates

How did I get that many dates to start with, you may ask? Well, for one, I put in a lot of effort into my profile. I updated my self-summary every now and then, added new photos, answered new match questions – all of these updates push your profile to the top of the news feed and encourages click-throughs. I also asked my friends what they thought of my profile so I get an outsider’s perspective on how I come across. I think this is the best advice I can give in regards to what you can proactively do to directly improve on your profile. I mean, if you have a boring life or if you’re uncomfortable with the way you look, you could probably acquire some hobbies or work on your appearance, but yeah, you are who you are and I’d rather help position you in your best light than turn you into someone you’re not.

I have initiated conversations with 8 out of the 53 people I went out with. As a woman, I receive a lot more messages than I send out, but I don’t have qualms initiating contact. Also, I don’t always get responses from those I message first. I don’t take that personally, since someone could be unresponsive for a multitude of non-me related reasons, such as being busy seeing a lot of other people or perhaps they are in the process of becoming exclusive with someone.

Also, it could simply be that the odds work for me, being an Asian female in America, where Asian women seem to be more popular.

Variables measured

Within my data set, I captured several variables, based on 1) the person, and 2) the circumstances of the first date.

The person
  • Age
  • Ethnicity
  • College
  • Highest level of education attained or attaining
  • Field of study
  • Current job
  • Whether they were an American citizen
  • Whether they’ve been in New York City for less than a year
  • Number of dates we’ve went on

The only subjective score in the whole data set was one I called Attractiveness. This was based on three broad categories: Looks, Voice, and Demeanor, which I combined to give people a rating of anywhere from 1 to 7. Why a 7-point scale? Because I liked that it had a mid-point and I liked that it was more nuanced than a 5-point scale but not overly complicated like a 9-point scale.

Looks is how pleasing to the eye I found someone. Do they have a handsome face? A good body? Luscious hair? Good style? I have a very particular look I find attractive (lean, fluffy dark hair, expressive eyes, fuller lips) so the closer someone is to this ideal, the higher their score would be.

Voice seems a little strange to call out but I love me an assertive, confident voice. I also like people who can articulate clearly and aren’t mumbly. I actually like a neutral American accent the best, and don’t care too much for stereotypically sexy Romance language accents – it’s harder for me to understand. I don’t like squeaky, drawly voices, vocal tics like excessive use of “like” or lisps or stuttering – although who am I to talk, I still have a Singaporean inflection and I have a braces-induced lisp D:

Demeanor is a really broad one, which applies mostly to body language. In general, I like good posture, ease of movement and comfort with eye contact. Demeanor also includes appropriate physical touch, knowing how to communicate with waitstaff, and chewing with their mouths closed. I would rate someone more poorly if they were slouchy, overly fidgety, overly stiff, or had poor etiquette.

The first date

I also captured some variables surrounding the circumstances of the first date. I wanted to get a sense of the kinds of first dates that were more likely to lead to subsequent dates.

  • Date of first encounter
  • Did we go out during the day or at night?
  • Did we meet up during the week or during the weekend?
  • Did we drink alcohol?
  • Did we make out? (which is a peck and beyond)
  • Did I initiate the kiss? (Sometimes women do this!)
  • Did he spend more than $80 on the first date?
  • Did he call me at any point before the second date?


The Long Tail of Dates

 photo long tail.png

Like what mirrors the experience of many others, several of my dates ceased to be after the first three dates. I’d say that the biggest issue that inhibits dates #2 and #3 from happening is simply a lack of conversational chemistry. Most people usually look like their photos and I can handle a few more pounds or a few more wrinkles. Some people can be really similar to me on paper, but conversation could simply be stilted or it could be overly contrived. It’s surprisingly difficult to develop chemistry when two people are seasoned daters and are very loquacious but are just slightly impersonal.

The second biggest issue would be a lack of physical chemistry. My orifices shrink into tight “NO ENTRY” zones when encountering a sloppy kisser or a handsy groper. On the other hand, hesitant wusses also turn me off. (“Why won’t you take me already?!”) At the end of the day, I think it’s about how two people get along with each other. One person’s delicate touch could be another person’s irritating flutter. Someone’s passionate French kiss could feel gag-inducing. If we don’t match, then we don’t match.

Date #3 is an important date. The Three Date Rule is a “rule of thumb which states that the third date is a milestone in determining whether a woman or man will consent to sexual intimacy”. I hate possessing knowledge of this rule, because I feel like there are societal expectations of how soon sexual intimacy should occur and there’s a lot of pressure that happens on both ends because of it. Post date #3, there’s often a little bit more expectation about the dating turning into something more. Some connection has been established. The question then becomes – where is this leading towards? That’s when conversations about managing expectations could come in handy 😉


 photo Screen Shot 2015-02-01 at 3.18.05 PM.png

The problem with demographics is that my preferences became more and more skewed through time. When I encountered success dating Jewish men, I sought out Jewish men. Recall how I joined JDate? I partially wanted to test the hypothesis that Jewish men were compatible with Asian women due to cultural similarities such as emphasis on education and humility. Here are my thoughts about JDate after having been there on two months – I am not specifically looking for a Jewish mate and will not use it again. The UI sucks and I crave a little more diversity.

When I encountered success with software developers, I kept going out with them too. (They’re also a dime a dozen on OkCupid.) I decided that Ivy League was not worth optimizing towards because of its Northeast-centric worldview and thus is at a paltry 32%.

Now for some fun findings! Let me caveat AGAIN that my sample size is small, I have very obvious biases, and this is in no way gospel for how I feel now, 8 months later.

 photo Screen Shot 2015-02-01 at 4.30.47 PM.png

Pretty obvious trends here. The more attractive I found someone, the more dates I’d go on with them. I’d also be less likely to be able to keep my hands off someone if they’re better looking. I’ve heard anecdotally that women don’t really initiate kisses. That’s too bad, isn’t it? >:-P

 photo Screen Shot 2015-02-01 at 4.42.45 PM.png

Attractiveness by ethnicity is a little dicier to interpret. Do I find Asian men more attractive, or do Asian men have to over-index the average guy for me to go out with them? Is it the case that Jewish men are less attractive or that I went out with less attractive Jewish men because being Jewish superseded their appearance? (I only went out with one black guy, so I’m not sure it’s worth commenting on. But incidentally he was British…)

 photo Screen Shot 2015-02-02 at 8.37.30 PM.png

I think I know why doctors (or doctors-to-be) do so well. They do really well on the Voice and Demeanor front. The few that I have gone out with have an assured, well-paced manner of speech that’s not peppered with redundant filler words and they tend to make physical contact readily but not aggressively. I attribute this to training in bedside manner. Since this data set, I have gone out with physicians who do NOT fulfill these criteria – the spell has been somewhat broken.

 photo Screen Shot 2015-02-01 at 4.21.48 PM.png

Part of why I was attracted to older Jewish men was their generosity and chivalry. I liked that they tended to call me instead of text me. I liked that they’d spend more money on first dates. From my little data set, the stereotype of nice Jewish guy seems to hold true.

One other thing to consider is that I may have reserved primetime (weekend night) for a high-potential date, which may have then led to a self-fulfilling prophecy. But I do know that I like fancy cocktails at speakeasies, livin’ up the urban New York life.


How exhausting was the process, mentally and emotionally?

You know how the busier you are, the more productive you get? That was the case for me. If my calendar was only 50% full, my free time was a lot less productive. But since my calendar was 90% full, I was very efficient with every minute of my time. Being productive felt amazing. Keeping up with the spreadsheet was also easy. I had two sheets – one sheet to track variables after meeting someone for the first time, the second sheet to track two columns: that day’s date and the person I saw on that day. It was easy to “play” hard-to-get, simply because I was just that unavailable.

Emotionally, I spent most of my time hung up on the one person I had seen the most. Knowing that 13 Dates Guy liked me enough to spend time with me but was not interested enough to commit was very difficult for me. I was not really emotionally invested in anyone else, although I tried to remind myself there were plenty of fish in the sea. (How emotionally invested can you get after a handful of dates, anyway?)

Would you encourage keeping a data set of my own?

No. It’s obsessive and encourages overanalyzing. There will always be variables you have failed to consider because relationships are messy business. It also shifts the focus from adapting to people’s variances to making sure your data set doesn’t have any anomalies in it by arbitrarily refusing to go on dates with certain people. But you know, it is fun… just remember to keep your eye on the prize 🙂

Did you discuss your data set with your dates?

Sometimes. Most people who liked me enjoyed the fact that I have one. Many of them preferred not to be privy to its contents, which I respected as a self-preserving mechanism. It’s like, for instance, I could be really appreciative that my boyfriend is a great kisser, but thinking about how he acquired those skills would be unnecessarily upsetting.

Did you get a lot of free dinners?

No. In fact, I would spend more money on dining out because I wouldn’t have time during the evenings or weekends to leisurely go grocery shopping and plan out my meals. I also like to offer to pay for dates once we have sufficient traction going. I did lose weight though, because I’d hardly eat dinner and merely ingest alcoholic calories for dinner.

What made someone someone you fell for and someone you didn’t?

This is a hard question. I wish I knew the answer to this one. Of course there are some baseline criteria like being reasonably attractive and being nice. At the same time, you can take someone who checks all the boxes but simply doesn’t incite strong feelings. Or you could have someone who incites strong feelings in you and checks off criteria but you could begin questioning the validity of your feelings or the criteria.

I think, at the end of the day, a relationship working out is some constellation of physical attraction, intellectual chemistry, and a willingness to give yourself to the other person/let go of your reservations. I think what has been the consistent cause for failure in my relationships is the last one. We have been hesitant to be vulnerable, or unwilling to commit. Other times, I want nothing more than to make him happy and give my all, and am in full knowledge that he’ll appreciate and reciprocate. Who knows where the source of this impulse is? Will I feel this way if I find a hot doctor who’d spend >$80 on our first date that he called to schedule? Or is it because he’s just him, whom I met at that specific time, at our respective emotional readiness? (Sometimes the fortuitousness of a romantic match occurring is so awe-inspiring to think about.)

How could you have possibly justified finding love by using data? That seems to demean the whole idea of love.

I was genuinely interested in the people I went out with, and chose to go out with again. I was interested in people’s stories, and I did develop feelings for some people. The dates weren’t a means to a data-mining end – the spreadsheet was the means to the end – love. Amy Webb and Chris McKinlay are with me.

Are you a hot female cyborg?

Maybe. *beep-boop-beep-boop*


The Author

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

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