Dating Advice from Philosophers

Public domain

Niccolo Machiavelli

Dear Machiavelli,

My friends want to throw me a bachelor party. Knowing them, it will involve strippers, booze, drugs, the works. I promised my fiancée I would stay away from that kind of stuff, but I’m really tempted to go, and I’d hate to let the guys down. What should I do?



My Liege,

I am unsure how to advise you in this instance, for your status in this world has much bearing on the matter. Are you a common man, or are you a prince? For it is well known that those actions which are considered most virtuous in a common man are in fact a vice in a prince, and that which would be vice for the lowest laborer is in fact raised to holy virtue when undertaken by a prince. Be you of the lower classes, stay true to your course and all will be well. Be you my liege, I pray you, indulge yourself.

Public domain (ironic, isn’t it?)

Adam Smith

Dear Adam Smith,

I’m meeting a girl for a first date, and I’m not sure what I should bring. I know tradition calls for flowers and chocolates, but do modern ladies still go for that sort of thing? Or would I just come across old fashioned?


Lonely and Confused

Dear Consumer,

The women of this age are as they have always been and as they shall always be, a part of the broader tapestry of our economic fabric. To deny that is to deny the truth of what makes all nations mighty. If you would impress and woo the lady, I would suggest you show her that you care for your nation by supporting the lifeblood of the nation: commerce. Support the florist, the chocolatier, yea, even the dressmaker and the milliner. In this way you shall prove you are a great philanthropist as well as a mighty provider.

Public domain

Friedrich Nietzsche

Dear Nietzsche,

My girlfriend and I have been together for over two years, and we love each other very much. I’m thinking about proposing, but there’s just one problem. Ever since she was a little girl, she’s had this dream of a big church wedding. I’m agnostic, and both of my parents are atheists. I just don’t see that working out. Can you help?


In Love but Not In Church

Dear Superman,

Ah, women. They make the highs higher and the lows more frequent. Every church is a stone on the grave of a god-man: it does not want him to rise up again under any circumstances. Is life not a thousand times too short for us to bore ourselves? It is not a lack of love, but a lack of friendship that makes unhappy marriages. Love is blind; friendship closes its eyes.

What I’m saying here is just rent out the local VFW Hall.

© Marie-Lan Nguyen / Wikimedia Commons


Dear Plato,

My boyfriend cheated on me a few months ago, and I just can’t seem to let it go. I still care about him, but I can’t get past this, and it is ruining our relationship. Should I forgive him or should I move on?



Dear Prisoner,

What you fail to understand is that your concerns are not real. They are simply the shadows of old wounds that you cling to out of fear of losing the illusions you have lived with all your life. Throw off the shackles of your fear, and acknowledge that which torments you is naught but a specter cast by the flickering light of a neon vacancy sign. Do not turn your anger on those who would drag you into the light of truth, but rather on the one who has in truth earned it, and kick him to the curb.

Like the sun, wind, and water, this photo is public domain.


Dear Laozi,

I feel as though my life has been spiraling out of control lately, and I just don’t know what to do. I am looking for some sense of balance, but I can’t abandon my wife to withdraw from society and meditate in nature for a lifetime. Is there some weekend course I can take to achieve enlightenment quickly?


Seeker of Truth

Dear Ineffable One,

While in days past the search for the Tao could take a lifetime, modern society no longer has the proper respect for the venerable sage. Where the strongest oak will break in a hurricane, the supple reed will simply bend. So too does the Eternal Tao adapt to change. If you seek to understand the Way, simply wear an outfit from JCPenney while eating a sandwich from Chick-Fil-A. In this way you will know balance.

© 663highland / GNU Free Documentation License v. 1.2

Sun Tzu

Dear Sun Tzu,

My name is Jenny and I am eight years old and there’s a boy I really like and I don’t know if he likes me back and I don’t know how to ask him if he likes me and I was wondering if you could tell me how I should ask him. Thank you very much for you help.

Your freind,


Dear Jen Ni,

The strong warrior charges in like an ox; the wise warrior is subtle and flows like water. To gauge your opponent’s intentions, send your most trusted lieutenant forward on a scouting mission to determine where he lies. If conditions seem favorable, I would suggest you send a missive of alliance, stating your intentions indirectly yet plainly, constraining your opponent’s choices to those that you would find most favorable: “Do you like me? Yes_ Very Much_”

For more, check out “Dating Advice From Historical Figures“, “Dating Advice From Mythological Creatures“, and “Dating Advice From Classical Deities“.

153 Comments on “Dating Advice from Philosophers”

  1. A later economist might have suggested buying only a single chocolate due to the law of diminishing returns. Adam Smith was a good choice.

    • Bob Bonsall says:

      On the other hand, Keynes might have suggested getting the government to buy several boxes of chocolates to boost the economy. You never can tell. Thanks for reading!

  2. Priya says:

    Reblogged this on Much Ado About Nothing and commented:
    This is the best thing I’ve read in a while…

  3. bellesogni says:

    Do I like this post? Yes! Very much!

  4. Ramin Tork says:

    This was really hilarious. Have you been listening to Philosophy Bites Podcasts like I have?

    • Bob Bonsall says:

      I have not been, but I will give them a try. I did just finish a course on Asian religion and philosophy, which is what inspired me to write about Lao-Tzu.

      • Can you make one for Confucius then? I’m curious how that would be like.

      • Bob Bonsall says:

        I’ll definitely be thinking about it. As I may have mentioned before, I’m trying to follow my wife’s advice to stretch myself artistically (her words, not mine, lest I come off conceited), so I probably won’t be going back to the dating well for a while. But not to fret, I will be doing another at some point, and he’s definitely on the list. Anyone with such concern for being a gentleman must have great advice to give on dating, right?

      • That’s great, Bob. I will be waiting for it. This post made my day. Thanks for making me laugh like crazy.

  5. free penny press says:

    Hands down, best Freshly Pressed I’ved ever read.. This is witty, well thought out writing..
    Well done!!

  6. Reblogged this on OurBrainHurtsAlot and commented:
    This is one of the most funny and informative articles out there.

  7. This is epic, I’m reblogging this, you should do one with Dante Alighieri talking about Beatrice 🙂

  8. jensine says:

    at least i now know it’s not just me

  9. LaQuita says:

    Very well…made me laugh..thank you for your philosophical view at 21st century issues

  10. David says:

    Brilliant work, Bob. Thanks for the laughs; I needed them greatly =)

  11. Writer_Indu says:

    Thanks for the write-up. I had a good laugh.

  12. idogiveanf says:

    Allow me to reblog this. Hehehe.

  13. idogiveanf says:

    Reblogged this on IdogiveanF and commented:
    This gave me a good laugh. =) Dating tips from the greatest philosophers of all time, anyone?

  14. please write more articles of this nature.
    – a funloving , goofy, never delivers a punchline, music lover.

  15. NomadSage says:

    Wonderful and hilarious.

  16. petitechoux says:

    Reblogged this on [Mis]adventures of My Newly Single Life and commented:
    This is absolutely the wittiest and smartly written posts I’ve ever read! The combination of history, humour and relationships will definitely make y’all chuckle!


  17. “What I’m saying here is just rent out the local VFW Hall.”

    This is brilliant, good sir. I wish Nietzsche ended everything he wrote with that line. He dedicated his entire life for the promotion of local VFW Halls.

  18. maria precioso says:

    very witty!

  19. Mercedes says:

    This was great! You should do one with Descartes. I’d love to read that one.

  20. Marian Green says:

    The last one is my fav!!! Really smart post!

  21. jamesroom964x says:

    Very funny, you definitely have a handle on their writing styles as well. Especially liked Sun Tzu, he always was the cautious one, much like an eight year old girl!

  22. curleduptoes says:

    Awesome post. Awesome! Reblogged 🙂

  23. Kiya Krier - Runs With Blisters says:

    Hahah! Takes me back to college & ‘Western Civilization’ class. We read many of these guys 🙂

  24. Henry David Thoreau would recommend to retreat to the forest for a few years.

  25. utesmile says:

    Fantastic post, very creatife and funny. Great idea and good advice from the wise men!

  26. KOKAY says:

    I was able to hold on to my chair til the “Dear Jen Ni” bit! That just killed me!

  27. I very much enjoyed this, Bob. Thanks for taking the time to write and share it with us.

  28. ejane01 says:

    I just read The Prince so this was very topical for me! Very funny!

  29. BroniaM says:

    very delightful… nice way to unwind after a hectic day. enjoyed it.

  30. BroniaM says:

    thoroughly enjoyed it. very delightful. great post.

  31. Eating Chick-Fil-A in an outfit purchased from JCP. That just made my day. Ah, to be so full of wit.

    Lovely post!

  32. Anarya Andir says:

    This post is so funny! Loved it. You’re awesome! You’re like the perfect author actor (yeah I’m making up a term like that). But you wrote these so fittingly that I could imagine all these philosophers saying these things. Congrats on being Freshly Pressed. Well deserved!

  33. kristennemarie says:

    Funny post 🙂 This gives a lighter side on the usually serious aura of philosophers 🙂

  34. Very entertaining! I love Laozi’s suggestion for finding balance. These philosophers do have a few good insights on dating 😉

  35. Raniel says:

    Great post! 😀

    Would also have loved to see what Foucault, Sartre, and Derrida might say. But I liked the Nietzsche bit.

  36. mechasketch says:

    HAHAHAHAHAHAHAHAHAHAHAHAHAHA….I would say something else but really my internet laughter just about does it. This was fricking hysterical.

  37. Fitch says:

    Lost my shit reading Sun Tzu and Laozi; this is incredibly hilarious.

  38. Elena says:

    Great! You can’g go wrong with philosophy…. right?

  39. POKA-rt Scrapbook page says:

    nomnomnomnom (**,)
    Write more!!!
    Absolutely Fabulous

  40. blog says:

    I’ve gone ahead and bookmarked at so my friends can see it too. I simply used Dating Advice from Philosophers My Not So Humble Opinion as the entry title in my bookmark, as I figured if it is good enough for you to title your blog post that, then you probably would like to see it bookmarked the same way.

  41. Laura Reese says:

    Love it!! FUN and smart!!

    xx, Lauren

  42. Don Bross says:

    You need more readers, how isn’t this filled with comments!

  43. […] hilarious and this is a well written piece. If you missed the previous post he did called Dating Advice From Philosophers, you BEST get up all in that. It’s equally entertaining and definitely breaks up the monotony […]

  44. The Writer says:

    Reblogged this on and commented:
    Re-read this, and had to bring it back because I think it’s rather clever.

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