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. Hillllarious and très clever ! Sometimes I think of Ben Franklin’s direct and quite thorough advice to stick with older women and it is so amusing.

  2. skyride says:

    Great post.
    The greatest minds in history, right? What a bunch of assholes… You were spot on with the advice they’d probably give. Nietzsche’s letter– hilarious.
    Congrats of Fresh Pressed! 🙂

  3. hilarious! very wise, yet relevant advice.

  4. Simply brilliant. Specially the advise of Sun Tzu to Jen Ni.

  5. poignantboy says:

    This is brilliant! Entertaining, and yet strangely informative.

  6. simonandfinn says:

    This was creative and fantastic!

  7. As a an admirer of the Tao of Piglet and the Te of Poo (or have I got it back to front?) I did enjoy your blog.

  8. Bob Bonsall says:

    Thank you everyone for all your support. Glad you enjoyed it!

  9. sholtosmith says:

    Very good

  10. J says:

    I don’t just like this. I LOOOOOOVE it!

    -Jen Ni (10 years older)

    PS Can you do one by Socrates next time?

  11. Wonderfully useless advice. Perfect.

  12. Ann says:

    Friedrich Nietzsche amused me the most…great post!

  13. debsimms says:

    Reblogged this on debsimms and commented:

  14. Reblogged this on lifeforevermore and commented:
    i just thought this is awesome!

  15. asoulwalker says:

    This is fabulous. Thank you.

  16. Brilliant! The kind of post I want to write. Thanks

  17. […] Dating Advice from Philosophers « My Not So Humble Opinion. Share this:EmailFacebookTwitterPrint […]

  18. Maahir Shah says:

    Hahaha! I love you for writing this!

  19. rachel bar says:

    Brilliant! What about Bill Gates’ opinion? Not a philosopher but it will be a new twist…

    • Bob Bonsall says:

      I’m already working on a follow-up, “More Dating Advice from Philosophers and Other Historical Figures”. I can’t promise who’ll be in there, but I welcome suggestions!

  20. Jane says:

    A very clever and enjoyable read!

  21. C.M.Hardin says:

    Brilliant. 😉

  22. mandyf says:

    Reblogged this on LGBT Nation.

  23. Melicus G says:

    Tzu is my favourite one! funnyyyyyyy

  24. patricemj says:

    This might be the best post on WP I’ve ever read. Please do not go away.

    • Bob Bonsall says:

      Wow, thank you. I promise I already have more in store, although I don’t know that it’s all quite this good. I’ll do my best to keep bringing the best content I can each time though!

  25. Farheen says:

    I really hate philosophy but I really enjoyed your post. Thanks for putting a different light on philosophers for me.

    • Bob Bonsall says:

      Glad you enjoyed it! I used to hate philosophy myself, then I finally found some good philosophy teachers who weren’t quite so full of themselves and found there are interesting ideas there. I don’t know that I would ask them for advice, but they did have interesting perspectives.

  26. Hahaha I love the Taoism references. The fact that an 8-year old girl is writing to Sun Tzu cracks me up!

    Nothings beats a good dose of Asian philosophy:)

    • Bob Bonsall says:

      Sun Tzu does seem to be a favorite. Maybe he should be a Kindergarten teacher… I already have another Asian philosopher in mind for the next round. Not gonna let it out of the bag just yet, but I hope I get the tone right.

  27. Sarah Doyle says:

    Pitch perfect for each of them — well done! Glad this got FP so I could see it. Congratulations!

  28. Nachiketa says:

    Haha! Loved the captions!

  29. mindrxn says:

    You have to do one for Socrates, lol. Really good post

  30. lsurrett2 says:

    Lightened my day! Thanks so much.

  31. This was a wonderful read. Very clever and so entertaining!

  32. This is brilliant! Congratulations on being Freshly Pressed – you deserve it! 🙂

  33. kai says:

    OH WOOOOW… This was INSANELY HILARIOUS!!!!!!!!!! Can’t stop laughing!!!!!!!!!!!

  34. kunu08 says:

    Reblogged this on RETROSPECT FOR LIFE and commented:

  35. Brilliant!!
    Funnily enough, yesterday I wrote a story about how my younger self was betrayed by her “most trusted lieutenant”. Sun Tzu didn’t mention that…

  36. natisimple says:

    Hi! Can I translate this post to spanish post it with full credits and link? The read was incredibly awesome.

  37. iRuniBreathe says:

    Clever! and appropriate advice for our times. Well done.


  38. Excellent post, very clever and original

  39. musabee says:

    Loved this! Brilliant.

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

  40. Most were amusing, but that last one? De-lightful. 🙂 Thank you for this break from seriousness.

  41. love this. has some of the same kind of stuff

  42. lovehaunt says:

    Jen Ni– good one! A thorough knowledge of both philosophy and the unnerving nature of marriage and relationship. Well done!

  43. Now, when asked for relationship advice, I can merely link here instead of having to think deeply about it. Thanks a lot; great blog.

  44. hmanlove says:

    Reblogged this on thistoryblog and commented:
    Creative, insightful, but mostly hilarious.

  45. amelie88 says:

    I’m not very well versed in philosophers and their philosophies but I am familiar with Machiavelli and I thought that one was funny! 😀

  46. dyefeltsool says:

    I thoroughly enjoyed that. Thank you!

  47. Super clever and funny. I loved the Plato one and may use that as an argument for cheating!

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