A Philosop(hic!)al take on Dating Conversations

“I wish I had a spreadsheet for that!”
“For what?”
“Those three girls that my mom set me up with. I need to date them in the next three months and close on one.”
“Perfect! Good for you! So what’d the spreadsheet do (you’re talking excel spreadsheet right ;))”
“Huh. Funny! Something like a comparative analysis sheet. With product questionnaires, valuation models and rating parameters.”
“Sure. Great idea Mr. Stock Analyst!”
“Yeah, you have a better one? You read philosophy… How would a philosopher go about this problem? What questions would your philosophers ask?”
“Hmmm… I don’t know… I’ll have to read up on that! You know, now that I think about it, philosophers don’t really mention dating that often. :?”
“Quite Surprising!”
“Yeah…. I guess the ones who have that aptitude, end up becoming poets or writers!”

It was probably the craziness of the Halloween weekend or something else (in my glass), but it actually got me thinking. What questions would philosophers like Aristotle and Plato or even our modern psychologists like Minsky and Daniel Gilbert ask when faced with this seemingly strange predicament of my friend. The kind of questions I’m referring to here are not the standard conversation-starter type first date questions that you can easily find using a simple search. And, nothing cracks me up more than the desi version of this search (did you see the 22 step wikihow link). BTW, both of these search queries are on Google’s auto-complete list, indicating how popular they are! This is something even Behavioral economists find quite interesting. e.g. Dan Ariely’s thoughts on dating (especially this one on dating questions and this story on dating biases).

Nonetheless, by the end of that Halloween weekend night, sitting in that downtown watering hole, we came up with the most hilariously amazing and insightful list of questions possible with that level of sobriety. In the true spirit of philosophy, the right answers to these would vary depending on who’s asking (and answering :P):

  • Assuming you were the last woman on earth in a desolate island, which one man would you prefer to have with you:
    1. A really good looking yet dumb actor
    2. A really smart, yet below average looking philosopher
    3. An ugly native of that island
    4. You’d rather kill yourself!
  • Assuming I gave you $10,000, what would you do with it:
    1. Spend it on stocks, double it, and return me $10,000
    2. Spend it on your looks, beauty makeup (ten grand get a lot of jobs done ;))
    3. Spend it on gifts for me – electronics, furniture etc.
    4. Other (please specify)
  • Assuming your house was burning, and you could save only one of these, which would it be:
    1. Your makeup kit and your favorite shoes and dresses
    2. Your memories – my gifts, our framed photos, mix-tapes, journals etc.
    3. Your documents – insurance, financial, SSN card etc.
    4. Other (please specify)
  • Assuming you were blessed with an infinite life , and God gave you one bonus gift, which of these would you pick:
    1. Eternal happiness
    2. Infinite life for me as well
    3. Infinite supply of money
    4. The sexiest body on the planet till eternity
  • Assuming you were NOT blessed with an infinite life, which of these would you pick:
    1. Absolute Wisdom
    2. Absolute Beauty
    3. Ten million dollars
    4. None. I’m happiest the way I am
  • Assuming you could take one last thirty day vacation in your life, starting tomorrow, where would you choose to spend it:
    1. Antarctica
    2. Paris
    3. At home – in the comfort of your couch and bed
    4. A monastery in Tibet
  • Assuming the Know it allentity (God or Whatever) allowed to pick one question, that It’d answer for you with it’s infinite wisdom, which of these would you choose:
    1. Who am I? (The ‘I’ here being you – just clarifying!)
    2. What is happiness?
    3. What is the purpose of my life?
    4. Not interested in knowing – Ignorance is bliss!
    5. Other – please specify

This one isn’t my joke, but something that is befitting as the last one on this post:


A boy is about to go on his first date, and is nervous about what to talk about. He asks his father for advice. The father replies: “My son, there are three subjects that always work. These are food, family, and philosophy.”

The boy picks up his date and they go to a soda fountain. Ice cream sodas in front of them, they stare at each other for a long time, as the boy’s nervousness builds. He remembers his father’s advice, and chooses the first topic. He asks the girl: “Do you like potato pancakes?” She says “No,” and the silence returns.

After a few more uncomfortable minutes, the boy thinks of his father’s suggestion and turns to the second item on the list. He asks, “Do you have a brother?” Again, the girl says “No” and there is silence once again.

The boy then plays his last card. He thinks of his father’s advice and asks the girl the following question: “If you had a brother, would he like potato pancakes?”



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One Response to “A Philosop(hic!)al take on Dating Conversations”

  1. How do you rate on my spillometer? « Says:

    […] « A Philosop(hic!)al take on Dating Conversations […]

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