Dating Advice From Famous Poets

Maya Angelou

By York College ISLGP [CC BY 2.0 (], via Wikimedia Commons

By York College ISLGP [CC BY 2.0 (, via Wikimedia Commons

Dear Ms. Angelou,

I’m writing to you because I’m quite vexed over my father’s intractable position vis-à-vis the proposal of my commencing a relationship with a boy. I am fully capable of making my own decisions, having already attained twelve full years of age, and while I have not yet reached menarche, I am still as much a woman grown as any of the other girls in my class, many of whom have already gone on one or more dates. I think he is being completely unreasonable. What say you?


A Caged Bird, Too


Dear Fledgling,

A free bird leaps
on the back of the wind
and risks unknown
are hers to embrace
without a care
to cast aside the chains
of a life left behind.

But a bird that stalks
down her narrow cage
held back by father’s
blindness and fear
her wings are clipped and
she knows not why
so she opens her throat to sing.

The caged bird sings
with a fearful trill
of things unknown
but longed for still
and her tune is heard
on the distant hill
for the caged bird
sings of freedom.

The free bird gets cruel education
on the price of casual flirtation
and the handsome boys not as good as their word
and her eyes with tears are blurred.

But a caged bird knows more than a father could
He’d lighten up if he understood
But he still says “no” and locks the doors
so she opens her throat to sing.

The caged bird sings
with a fearful trill
of things unknown
but longed for still
and her tune is heard
on the distant hill
for the caged bird
sings of freedom.


Edgar Allen Poe

Daguerreotype of Edgar Allan Poe, known as the "Annie" Daguerreotype.

Daguerreotype of Edgar Allan Poe, known as the “Annie” Daguerreotype.

Dear Mr. Poe,

I’m planning to propose to the love of my life, my beautiful girlfriend of many years, and I want to do it somewhere special, someplace so magical she’ll never forget it. Can you offer any suggestions?


Searching for the Moment


Dear Lost in the Moment,

It was many and many a year ago,
In a kingdom by the sea,
I proposed to a girl you may know
By the name of ANNABEL LEE;–

Let’s just say things didn’t exactly work out
The way that I thought they would be.
If I had it all to do over
In that kingdom by the sea,
We would have just gone out to a nice dinner–
I and my Annabel Lee.

My advice? Bundle up, stay inside, stay warm —


Dr. Seuss

Ted Geisel (Dr. Seuss) half-length portrait, seated at desk covered with his books / World Telegram & Sun photo by Al Ravenna

Ted Geisel (Dr. Seuss) half-length portrait, seated at desk covered with his books / World Telegram & Sun photo by Al Ravenna

Dear Dr. Seuss,

I’m not sure who to ask about this, but here goes. I’ve started noticing the boys in my class, and I think I like them, you know, in that way. Which would be great, except I’m a boy too.  Which I guess means I’m gay? And some people say being gay is bad, and other people say it’s not, and I just don’t know what to think. What do you think?


Confused and Lost


Dear Lost and Found,

There once was a girl named Julie Madevin,
A charming young thing the age of eleven.
She had a crush on a boy in her class,
The boy known as Billy Sassafrass.
Julie thought that he was quite alright;
His eyes were blue, his pants were tight.
But there was something the other kids would say:
They all insisted that Billy was gay.
Julie didn’t know what to do,
So she ran home and asked her mommies two.
They told her this was quite alright,
And Julie slept quite well that night.


Lord Byron

George Gordon Byron, 6th Baron Byron, by Richard Westall, from National Portrait Gallery, London.

George Gordon Byron, 6th Baron Byron, by Richard Westall, from National Portrait Gallery, London.

Dear Lord Byron,

I want to do something really special for my wife for Valentine’s Day this year. It’s been a rough year, and I really want to show her I love her more than anything in the world. You’re renowned as one of the greatest romantics of all time; can you please give me something to show her just how much I love her?


Truly Desperately In Love


Dear Truly Desperate,

I dunno. Flowers?




Dating Advice from Scientists

Marie CurieMarie Curie

Dear Madame Curie,

I desperately need the advice of a strong woman like you. I have a major crush on this guy at school, and I really want to tell him, but none of my friends like him. I’m also kind of a nerd, and he’s a football player, so I doubt he’d even be interested. Not to mention he probably doesn’t even know I exist. But I really do think he’s great. What should I do?


Unclear in Love

Dear Radiant Love,

Here’s the thing: I can see right through all of your excuses. You’re scared, and that’s understandable. What if he doesn’t feel the same way? What if things don’t work out? What if your parents forbid you to see him? What if, what if, what if…? But you need to take risks for the things you want in this world. Is there a chance you could get hurt? Of course there is, but nothing worthwhile comes without a price. If you truly wish to achieve success in life, regardless of your pursuit, you must commit yourself completely. Only then will you attain the prize you seek.



Heisenberg_10Werner Heisenberg

Dear Dr. Heisenberg,

I have been dating the same girl for a couple months now, and I thought everything was going just fine. Then the other week she started talking marriage. It seemed totally out of the blue to me, but she acted like it was the most natural thing in the world! It’s not that I’m totally against the idea of getting married, but I’m not sure we’re ready for that conversation yet, you know? Which one of us is right?


Uncertainly In Love

Dear Entangled Pair,

I understand your uncertainty, but you need to stand by your principles. You need to figure out where you are in this relationship before you decide how fast you want to move forward with it. While it may feel as if your partner is exerting an irresistible force on you, you need to remain positive and understand that you are not merely a neutral observer in this. You have to take charge and decide for yourself what you want, and then communicate that effectively. The release in tension you feel will be massive.



Albert Einstein


Dear Mr. Einstein sir,

My name is Jenny and I have a problem and I hope you can help me. I was going stedy with a boy at skool and I thout everything was fine and I really liked him and I thought he really liked me and then one day he really didn’t like me anymore and now Im very sad and I don’t know what to do.

Your Friend,


Dear Fräulein,

Ach, the ways of love are more mysterious than the ways of the cosmos. It is easier to understand the structure of the universe than the structure of a man’s heart. Sadly, it has been my experience that emotions, much like matter and energy, can never truly be destroyed; they can only be changed from one to another. In this same way it seems as if this young man who once professed to have a deep Liebe for you has now seen it transformed in the crucible of time to its opposite. I can only offer you the solace of knowing that as strong as his passion is now so it was then, and if you can find the source of the change you may be able to turn him back if it is not too late and you are still interested in making the effort.





Dear Pythagoras,

I’ve gotten myself into a pickle and I can’t see a way out. There’s a girl I’ve been with for a couple years, and the truth is we only started dating because nobody else would have either one of us. At the time I was kind of chunky, and she’s… well, she’s kind of plain on a good day. She’s a good friend, and we enjoy a lot of the same things, but there’s no real spark. This summer I started working out a lot and I finally got into shape. I also started getting some real attention from other girls, including a girl I’ve had my eye on for a long time. Would it be wrong of me to break it off with the girl I’m dating to pursue the girl I really want? Does that make me shallow that I’m that concerned about the way she looks?


Finally Buffed

Dear Muscular Mind,

I would theorize you have found yourself in a love triangle… without the love. It is a shame you do not feel eros for the lady you have, and the theia mania has been granted to you for one you have not, but the gods make fools of us all. Still, if philia is not enough to sustain you, and I have never seen it to be such in any man (and certainly not in a young man), it would be an unkindness bordering on cruelty to continue your current relationship regardless of whether your eye strays or if there are others who suddenly find you appealing. But before you sever the ties you have, consider carefully the value of what you are giving up. As you have changed, so may she; and what you once were you may be again. The alchemy of fitness may have worked wonders on a maiden’s eye, but it will do little to sway her heart, and you may find yourself twice alone and twice bereft before you know it.

Dating Advice From Classical Deities


Marie-Lan Nguyen / Wikimedia Commons (Public Domain)


Dear Hera,

I have been married for about six months now, and I’m starting to worry about my relationship. My husband and I used to go out all the time, but lately he stays late at work a lot, and when he comes home he just eats dinner and then watches TV until bedtime. He never seems to have time for me anymore, and on the weekend he goes out with his buddies. We don’t talk like we used to, and I’m afraid there may even be another woman. I’ve thought about looking through his email and his text messages, but if I didn’t find anything I’d feel like a horrible person, and if I did find something that would be even worse. I just don’t know what to do. Please help!


Desperate Housewife

Dear Concerned Matron,

It is an unfortunate fact that so many of our children have been raised on fairy tales to believe that all it takes is a magic ceremony to create the perfect circumstances for “happily ever after”. What the stories don’t prepare you for is the lifetime of work that follows. A marriage is more than simply living together in domestic bliss; it is a partnership, and one that must be cared for, nurtured, and treated well, lest it die from inattention. I am encouraged to hear you have not yet taken the irreversible step of violating your husband’s trust; a good marriage is built on trust and mutual respect, and once broken it can be almost impossible to recover. Believe in him, and surely you will be rewarded. Rather than snooping, try talking to him. Find a time when you can both be calm and relaxed and share your concerns; likely he has some of the same fears, and by sharing them you will strengthen your relationship. Confrontations don’t solve anything, but conversations can be the beginning of a better life for you both.


Tyr and Fenrir in for Our Fathers’ Godsaga by Viktor Rydberg/ Public Domain (Wikimedia Commons)


Dear Fenrir,

My family just doesn’t get me. They’re a bunch of straights, and I want to have fun while I’m still young enough to enjoy it! So I go out and have a good time, and yeah, I date some crazy women, but it’s not like I’m hurting anyone! I’m careful, I use protection, and we’re all consenting adults. Why can’t they just get off my back already?


Black Sheep

Dear Wild Child,

Family, am I right? You get just a little bit out of line and they can’t wait to chain you down with responsibilities and their “vision” of what you should be. Here’s the thing though: they really do care about you, and even though you think you’re not hurting anyone, you also may not be looking at the bigger picture. Are you considering where you’ll be in five years, or fifty? Parties are great while they last, but sooner or later the party winds down, and they’re worried you’ll be the lone wolf without anyone to go home to. Give it some thought, let them know you understand their fears and show them you have a handle on where your life is headed, and maybe they won’t object so much if you go out and howl at the moon once in a while.



Huitzilopochtli, from the Codex Telleriano-Remensis (16th century) (Public domain/Wikimedia Commons)

Dear Huitzilopochtli,

My girlfriend and I are always fighting. I have no idea why. Sometimes I think we just like to fight. The making-up part is great, but I’m not sure it’s worth it anymore. Half the time it seems like I’m in the doghouse for no reason at all, or just so she can lord it over me. I look at other guys’ relationships and it seems like this isn’t normal, so I’m wondering if it’s me, or us, or what. What should I do?


Tired of Fighting

Dear Warrior of Love,

The question you should be asking yourself is not “is this worth it?” but rather “why did we get together in the first place?” If the sole reason for your relationship is to provide some sort of spark or antagonism that each of you craves, even subconsciously, you need to break it off for both of your sakes. An addiction to drama is an addiction like any other, and continuing to feed it is a sure path to self-destruction. If there is something genuine in the relationship, you need to rediscover what it is that you mean to each other and find ways of resolving your conflicts properly. Patience, understanding, and communication are the way to resolve disputes. Fighting only leads to more fighting.



Curtis, Edward S. Indian Days of the Long Ago. Yonkers-on-Hudson: World Book Company, 1915. Page 84. (Public Domain/Wikimedia Commons)

Dear Coyote,

Theres a boy at school that is very good looking and very nice and all the girls like him and so do I and hes very nice and I think he might like me to but I dont know for sure and I’m not sure if I should ask him or not and even if I do I don’t know what to say and my mommy says I should play hard to get and I dont even knwo what that meens and I would like it if you could help me please thank you.

Your friend,


Dear Jenny,

Let me tell you a little story. Once there was a rabbit that was out on the plains, and this rabbit wanted to get a particularly appealing looking plant to eat. He thought he was a clever rabbit, so he hid out behind a rock, and waited until the sun had almost set. When he thought the time was just right, he bounced over and went for it, figuring it was late enough the snakes wouldn’t be out but too early for the owls. Well, he was right, but he forgot about just one thing: I’m not an early riser. The point of the story is fortune favors the bold. Be honest, don’t play games, just go on up to that young man and let him know you like him. Best case you found yourself a fine young man. Worst case? You found out he’s got poor taste before it’s too late.

Other posts you might like:

Dating Advice from Philosophers

Dating Advice from Historical Figures

Dating Advice from Mythological Creatures

Clean Sweep

I’d like to take this opportunity to explain to the ladies why it is that “men don’t clean”.

You see, this is a lie. A calumny. A slander of the highest proportion. We clean. We just don’t clean the way you clean. There is a difference.

You’re probably thinking right about now that I am simply making things up in an attempt to defend my gender, but the truth is I’m not. In fact, I’m going to paint a situation, walk you through it, and show you how every time you have been making false assumptions about men not cleaning.

Picture this: you ask your boyfriend/husband/son to clean a room. You leave for a half-hour, come back, and it looks no different to you, or at best only slightly tidied up. You say something to the effect of “I thought I asked you to clean in here,” and he maddeningly responds with “I did.” You can either exhort him to actually clean it or just give up in frustration now and do it yourself, because you know you’re going to have to do it anyway.

Sound familiar?

Now, let me explain what has happened.

You walked in to what, to a man’s eyes, appeared to be a clean-ish room. There might be a few things out of place, but overall it’s in decent shape. When you walked in and said “Could you please clean this room up?” the panic set in. He knows you think the room is filthy, but he has no idea why. He tries his best to guess what it is you want done, but he knows he is destined to fail. The only question is how much time does he intend to waste on this doomed effort. Some younger or over-eager fools will even spend more time and effort, thinking this will somehow earn them mercy. When you return and crush his spirit with an offhanded “I thought I asked you to clean in here”, her replies with the only defense he has, feeble though it may be: the truth. “I did.” He then watches you bustle around the room in a bad mood, engaged in arcane rituals that, when you are done, have made no discernible difference whatsoever.

Now, I know that sounds crazy, and that’s because it is. Men and women do not perceive the world in the same way. This is insane, but it is something that we simply have to accept. Ladies, what you need to understand is that, when you start going on about “cleaning”, we don’t share your vision. I don’t mean that in the sense of “I just don’t share your artistic vision”, I mean that in the sense of “I’m pretty sure you’re an insane cultist worshipping dark beings from beyond this reality and trying to summon them forth to devour our world”. But we love you anyway.

Because we love you, we want to make you happy. This is why we get scared and frustrated every time you say things like “please clean this room”. It’s like you’ve been watching the Saw franchise again, and you’ve decided that a combination of test and torture is just the thing to brighten an otherwise boring day. We both know there’s no way we’re going to win this one, but you ask anyway. Unless your purpose is to look for an excuse to get frustrated with us, perhaps the following advice will be useful to you.

First, keep in mind that we have different standards of “clean”. Remember the old saying about “if you want something done right”? Well, it applies doubly here. I’m not saying we’re going out of our way to shirk, but when you ask someone else to do something, you really can’t expect them to do it the way you would do it unless you’ve spent a few decades mercilessly drilling them on perfect technique.

Second, consider spending a few decades mercilessly drilling us on perfect technique. If you don’t have that much time to spare, some straightforward directions on what you’d like to see would be better upfront than a disappointed sigh on the back end. Keep in mind that if you do this you don’t get to say “well that was just for starters!” after the fact. Make the list comprehensive or don’t bother.

Third, are you familiar with the concept of “comparative advantage”? If you want the room cleaned just so, perhaps while you’re doing that he can be mowing the lawn. If you also want the lawn mowed just so, perhaps he can pay the bills. If you want that done just so, perhaps you would be more comfortable living alone.

Which brings me to my final piece of advice. Nobody is perfect, and we all find ways to annoy the crap out of each other on a daily basis. Learning to accept these foibles and follies is a big part of what makes relationships work, maybe the only part. After all, the rest is fun, not work. Focus more on the good times getting the rooms dirty than the confusion about trying to get them clean again.

For the rebuttal from My Not So Humble Wife, be sure to read “Dirty, Dirty Men“.

Dating Advice From Mythological Creatures


Dear Medusa,

I’ve been dating this girl for a few weeks now, and at first things seemed really great, but lately things haven’t been going so well. She’s started to criticize the way I dress, the way I talk, and even the people I hang out with. I like her a lot and I want to make her happy, but I’m not really comfortable with the way she’s been acting lately. My friends say I should ditch her, but I don’t think they “get” her the way I do, you know? What should I do?


Conflicted in Love

Dear Blinded by Lust,

I know you think you are in love, but the truth is you’re not. You are in lust. True love is something that you have with someone who not only accepts you for who you are, but embraces you that way, and loves you that way. They don’t have to love your friends the way you do, but they have to at least be willing to give them the benefit of the doubt as well. If you really want my advice, listen to your friends and leave this girl before you lose sight of the person you really are. Find a girl who isn’t going to try to change you into something that you’re not.



Dear Sphinx,

My boyfriend and I have a very rocky relationship. Sometimes things can be going along just fine, but then I’ll say something wrong and he’ll just fly off the handle. We’ll argue for a couple hours, and then we’ll realize that the whole thing was just a big misunderstanding. We make up and things will be fine for a few weeks, but then it happens again. He doesn’t normally have a short temper, so I’m starting to think it’s me. What should I do?


Tired of Fighting

Dear Pythia,

My first question would be why you go a few weeks without problems. If you find yourself walking around on eggshells trying to make him happy, then you are in an abusive relationship and need to get out before things escalate. However if it is as you say and it is simply a matter of the occasional argument, then I have to wonder what you’re not telling me. If there are major communication problems in your relationship, you need to either find a way to resolve them or else you need to find someone else. Clear communication, on both sides, is the key to any successful relationship. You don’t want to be with someone long-term who is going to bite your head off because you misunderstood something they said.



Dear Pegasus,

[Letter edited for privacy.] Should I or shouldn’t I?



Dear Star Struck,




Dear Fates,

I’ve just started dating the most amazing guy. He’s sweet, he’s kind, and he’s generous. We’ve only been together for a week, but I’m already pretty sure he could be “The One”. How do I know?


Ready for Commitment

Dear Overeager,

Ah, to be young and in love. The whole world seems fresh and new, and everything is in harmony. While we understand the desire to press forward and seize the moment, to try and capture it and spin about it a cocoon of certainty to last the ages, the future is as uncertain and unconstant for men as it is for gods. The only sure path is to worry not what the future may hold, but rather to embrace the present, enjoy today for what it is, and let things develop as they will. Tomorrow will come soon enough.



Dear Furies,

My girlfriend hates my family. I mean, not just hates, but HATES my family. I can’t really blame her, they’ve always been mean to her, but I still love them; they’re my family, you know? She’s made an ultimatum this year: either I spend Christmas with her or my family, but if I pick them I better find another date for New Year’s, if you know what I mean. I just don’t know what to do.


Pulled in Two Directions

Dear Inconstant Son,

We know all too well what it is you mean: that you are an ingrate. Your family has provided for you, nursed you, sheltered you, and you are unsure as to what your proper course of action is? For shame! You should be whipped and reviled! As for this wanton that would tear you from the loving arms of your family, be assured: anyone who would make you choose between them and your family is not worthwhile, and they have only given you the easiest choice you will ever have to make.



Deer Mermaid,

There was this boy I liked and he liked me and we liked each other I don’t just mean liked I mean REELY liked liked and then his mommy got a new job in another place and he had to move away and now I’m sad and what should I do?



Dear Jenny,

You poor girl, there is nothing so wonderful as first love, nor is there anything so tragic as love’s first heartbreak. I too know all too well the inconsistencies of men; the sweet promises they whisper, and yet they never stay for long. Always they long for the things they have left behind: their treasures, their vessels, their air. Take strength from this, sweet Jenny, and learn from it. For even as you have loved and lost, surely you will love again, and as my dear mother used to say to me, “there are plenty of men upon the land.”

Dating Advice From Historical Figures

Karl Marx

Karl Marx

Karl Marx would be happy to know this picture is in the public domain, giving according to its abilities, taking according to its needs.

Dear Karl Marx,

I have a question about blind dates. I haven’t been on the dating scene in a long time, and I’m not sure how to handle things. I’ve heard that the guy is supposed to pay for dinner, but I’m still struggling to get out from under some pretty horrendous student loans, and I can’t afford to be taking out a lot of girls I don’t even know, especially if things end up going nowhere. On the other hand, I don’t want to look cheap. What’s a guy to do?


Struggling in the New Economy

Dear Laborer,

It is truly disheartening to hear that even in this day and age the forms of capital are being used as a symbol of control in relationships rather than existing as a means to advance a fellowship of well-being and understanding. Ah, well; such is the way of the world until society is changed. In the meantime, I would advise you to reach out to those of your contemporaries who are of a similar understanding, building those relationships that you can gradually and with time, rather than with displays of bourgeois largesse. Perhaps meet her for a cup of coffee and discuss common interests so you can get to know her as a person; if she truly is a part of the struggle of the proletariat, she won’t mind going dutch.

Thomas Jefferson

Thomas Jefferson

We hold this truth to be self-evident: that this picture is in the public domain.

Dear Thomas Jefferson,

I’ve got a serious problem and I’ pretty sure only you can help. I was at a party a few weeks ago, I got kind of drunk, and I ended up hooking up with this girl. Thing is, she wasn’t my girlfriend. I feel awful about it, but I don’t know what to do. I haven’t told my girlfriend about it, and I’m wondering if I should. I really love her, and I think she’d forgive me, but would it be right?


Too Much Southern Comfort

Dear Southern Man,

When you choose to overindulge in spirits, there is a race to determine whether you run out of wisdom or honor first; the only certainty, as you have found, is that you will lose. In this instance, your impulse to unburden your conscience to your long-suffering significant other is not one born out of compassion, but rather one of guilt and further self-indulgence. The only course of action open to you at this point is to bear the knowledge of your misdeeds alone; keep your own counsel on this matter of impropriety, and let history be your judge.

Sigmund Freud

Sigmund Freud

Sometimes a cigar is just a cigar, but this photo is always in the public domain.

Dear Sigmund Freud,

I’ve been with this girl for a while now, and things are getting pretty serious. I’m starting to think she might be The One. But how do you tell? I mean, I’m talking about making a commitment for the rest of my life. How can you be sure about something like that?


Ready to Make the Leap

Dear Superego,

It is understandable that you are hesitant about such a major life change, and decisions of such gravity bring a great deal of internal strife to everyone. Before settling on a course of action, explore your motivations; consider what might be driving you to take your relationship to this new and deeper level. Is it this girl in particular that makes you feel ready for a lifelong commitment, or are you simply responding to a suppressed need yet unfulfilled? While you’re at it, take a good look at her mother, because that’s what you’ll be married to in twenty years.

Abraham Lincoln

Abraham Lincoln

Public domain.

Dear Abraham Lincoln,

I’ve been married for a few months now, and I’m worried our life has gotten to be kind of routine. I want to mix things up a little bit, try to get “out of the rut”, but I’m not sure how. Do you have any suggestions of some fun, adventurous things we can do together?


Looking for Adventure

Dear Citizen of the Republic,

While I certainly respect and admire your desire to preserve the union you have with your wife, I wonder if you have given full thought to the many options available to you. While the drive for glory may seem attractive now, it soon pales before the simpler pleasures of hearth and home. May I suggest instead a special night in? Cook your new wife dinner; make some light conversation; perhaps a game of charades. Going out on the town is overrated.

Napoleon Bonaparte

Napoleon Bonaparte

Public domain.

Dear Mr. Napolean,

I had this guy I really liked and I thought he liked me to and I had a friend who was supposed to ask him if he liked me so I could find out if he liked me like I liked him but instead she asked him if he liked her and now they’re going together and I’m sad. Even worse all my other freinds arent talking to me because I said she was a poopyhead. What should I do?

Your firend,


Dear Mademoiselle Jennifer,

I also understand the pain of betrayal; to feel as if you are the emperor of the world one moment and a mere exile from all that you know the next. But fear not! With sufficient effort and planning, you can stage a coup d’etat against those who rule your current circumstances, and once again take your rightful place in your social circle. Make use of what you know about those who stand against you, and do not hesitate to spread their most shameful secrets to the world. Press your advantage ruthlessly, and crush them utterly. Do not forget that this is war; you do this not out of revenge, but to teach a lesson to others who might be tempted to stand against you, and to prevent further battle in the days to come.



A true gentleman would know this is in the public domain.

Dear Confucius,

There’s a girl I go to college with that I’d really like to get to know better. We take a few classes together, but I haven’t gotten up the nerve to ask her out yet. I’m not sure if she’d be interested in me, and I’d be devastated if she turned me down. Should I go for it, or should I just try to stay friends?


Pining Away

Dear Junzi,

It is well that you are in college, for the pursuit of knowledge is in itself a part of the path of virtue. It is however only one part; self-knowledge, the cultivation of virtue, and filial duty also play their roles. If you are a true gentleman, what woman would refuse you? You say you have classes in common; surely that is something you can use as a place to start a meaningful interaction. Failing that, try taking her father out for a round of golf.

The Dating Rorschach Test

I’m sure everyone has their own guidelines for what makes a good relationship. Between two friends of mine I have heard the entire spectrum, from a simple “am I as happy with this person three months in as I was the day we first met?” to a test that runs to several pages (I am not making this up). For myself, I long ago developed my own simple guidelines that have worked exceptionally well, and that I am at last ready to share with the world. They are as follows:

  1. Can I wake up next to this person without flinching?
  2. Can I put up with their shit?
  3. Can they put up with my shit?

Now, before I catch any grief over these questions, allow me to point out that this is the Dating Rorschach Test™. What you get out of it is what you put into it. Let’s take it one question at a time and you’ll see what I mean.

Can I wake up next to this person without flinching?

I’ll admit it, when I first came up with this question, I was about 15, and it was my entire standard for dating. And yes, it was all about looks. But then, as I got into my early twenties, it took on new depth and dimensions, like carefully leaning over and checking her ID, hoping not to wake her while I make sure I won’t get arrested- well, anyway, the point is I grew as a person. By the time I met the woman who would become my wife this question took on some real meaning. Will I still have self-respect when I wake up? Can I seriously see myself discussing matters of import with her? Does she fulfill my intellectual and emotional needs as well as being beautiful? (Hey, I never said I stopped being shallow). So what do you need in order to be able to wake up next to someone without flinching?

Can I put up with their shit?

I added this one in when I was about nineteen or so, after a string of short, tumultuous, and painful relationships that seemed to have one common thread: wacko girlfriends. I was absolutely convinced that every single girl I had dated to that point was batshit crazy. Quite the coincidence, and if I had any concept of basic probability I would have seen the flaw in my logic, but it took another few years for me to sort that one out (see below for that). The one good thing that came out of it was that I was able to recognize that, if I was going to sustain any kind of relationship, I was either going to have to find the perfect woman who had no flaws whatsoever and then convince her that she wanted to date me, or I would have to learn to live with another human being’s imperfections. All evidence to the contrary notwithstanding, even I didn’t have the kind of hubris necessary for option A, so I went with B. I know this doesn’t sound like much of a leap, but seriously, I’ve seen a lot of “adults” who still need to pick up on this one, so cut my younger self a little slack. The key, I realized, was to find someone whose craziness was compatible with mine, or that I at least didn’t find too noxious.

What does this mean for you? Whatever you need it to mean. Does leaving dirty socks on the floor drive you crazy? How about owning too many shoes? How do you feel about Friday night being “hangin’ with my boys night”? Or saying “whatever” and walking away being considered a perfectly acceptable way to end a conversation? Think about it, because what seems cute now might getting annoying a year from now, and what’s annoying now will drive you batshit crazy a year from now. And after almost a decade dating and married with my wife, I can say this is one of the most important points to consider. The other one is…

Can they put up with my shit?

So it wasn’t until I was in my mid-twenties that I figured this one out. As one Demotivational poster points out, “The only consistent feature in all of your dissatisfying relationships is you.” I finally realized that it’s not enough for me to be happy with the person I’m with; it might be within the realm of possibility that it’s just barely a chance there could be some fraction of a notional option of a thought I could be somewhat close to less than perfect (I’m able to acknowledge my flaws). Put another way, I’m an acquired taste. I may even have the occasional annoying habit, like leaving dirty socks on the floor, according to my wife. Although I still swear that was the dog. That we didn’t get until we had been married for a year. He has a time machine, like Mr. Peabody. He’s been using it to get me in trouble for years.

The point is tolerance in a relationship is a two-way street. We always think of relationships as being about love and respect and sex and sunshine and rainbows and all that jazz, but the reality day to day is that more often than not relationships are about listening to somebody tell the same story you’ve already heard a hundred times and I really don’t care about your level twenty barbarian honey but you go ahead and tell me anyway if it’ll make you happy and- sorry, got a little carried away there. What was I saying? Oh yeah. The point is relationships are about living with another person, in close proximity, every day, hopefully for the rest of your life. That’s a recipe for friction more often than happiness, which is why you need to find someone who can tolerate your bad habits, whether it’s leaving dirty socks lying around, telling the same stupid stories over and over, or blaming it all on the dog.

The Dating Rorschach Test

So there you have it. Maybe you agree, maybe you don’t. Maybe you have your own standards for finding a mate. But at least I can say mine worked for me. And in the end, that’s all I ever wanted out of it.

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“.

Don’t Hate the Player, Hate the Played

I’ve already given guys a blast of bile for their pathetic attempts at making women the source of their perpetual dating woes, so I feel it’s only fair that I turn the petty hate machine (dodged that copyright bullet!) on the gentler sex. One of the biggest issues I have with women, and this is not all women but a significant enough minority to be worth mentioning, is the ones who engage in the following pattern:

  • Date “the wrong guy”.
  • Insist on making an issue out of it/complaining about it. Loudly.
  • Go back to him for more. Repeatedly.
  • Finally break up with him.
  • Rinse and repeat.

“How do I always find myself in this position?” is a refrain I have often heard. Let me answer that bluntly: by opening your eyes after you have already put yourself in that position. No, I’m not trying to blame the victim here, I’m trying to get everybody, men and women alike, to start taking responsibility for the choices they make and the consequences of those choices. Let me play Jacob Marley for a moment and introduce you to the Ghosts of Your Choices Past, Present, and Future. They may help shed some light on the reasons you end up reliving the same “relationships” over and over.

Going to clubs and bars to meet men. I’ve heard that women go to clubs to dance and have a good time. This is a foreign concept to me and every straight man in existence (I can’t speak for the gay men, although the ones I have known generally favored clubbing as a means of picking up guys as well.) That’s the first strike against meeting someone at a club; you’re there for two completely different reasons. You may want to meet someone to hang out with; he’s there to meet someone to hook up with. Even if you are both interested in more than a one night – if that – stand, consider the environment of a club. It’s crowded, loud, dark except for the flashing lights, and oh yeah, you and everybody else is likely to be drunk. So your expectation is that… he’s going to be charmed by your rapier wit? The depth of your knowledge on the Crimean War? Or the tattoo of Mickey Mouse on your thigh? Speaking of which…

Dressing like a whore. Dave Chappelle covered this one already in Killin’Them Softly, so I’m just going to quote him verbatim: “The girl says ‘Oh uh-uh, wait a minute! Wait a minute! Just because I’m dressed this way does not make me a whore!’ Which is true. Gentlemen, that is true. Just because they dress a certain way doesn’t mean they are a certain way. Don’t ever forget it. But ladies, you must understand that is fucking confusing. It just is. Now that would be like me, Dave Chappelle, the comedian, walking down the street in a cop uniform. Somebody might run up on me, saying, ‘Oh, thank God. Officer, help us! Come on. They’re over here. Help us!’ ‘Oh-hoh! Just because I’m dressed this way does not make me a police officer!’ See what I mean? All right, ladies, fine. You are not a whore. But you are wearing a whore’s uniform.”

Showing no respect for yourself. This goes well beyond where you go or how you dress. This goes into how you approach your entire life. Simply put, when 90% of your time in a given situation is misery, and you stay in that situation, you are not respecting yourself. I don’t care if this is a relationship, a job, a housing situation, time with a “friend” (why do we even need the term “frienemy” anyway?), or anything else. No, life is not perfect, and sometimes you have to suck it up. But just because 10% is great does not justify the other 90% being misery. Stand up for yourself, treat yourself right, and don’t let others treat you differently.

Showing no respect for the men you date. Ever wonder why you can’t keep a good man? Take a look at the way you treat them. There are women who take advantage of men, use them as walking credit cards, ignore their emotional needs, dump on them all the time, screech at them and deride them. My favorite is the physical abuse double standard. “Gentlemen don’t hit ladies.” “It was just a little tap.” “Oh, get over it you big baby.”  And then they wonder why he left. Here’s a hint: spend one day letting a guy treat you the way you treated him. Be honest. See if you can make it a full twenty-four.

At the end of the day, you picked them. Here’s a hint: if you have ever uttered the words “you’re a nice guy, but…” to a guy who has asked you out, you are part of the problem, not the solution, and I’ll tell you why. Option one is you lied to him. He’s not a nice guy, you would never date him, and in fact you are looking for someone to recue you at this moment. Unless you are in fear for your physical health, this is a cheap cop-out. Option two is that you do mean it, he is a nice guy, but you just can’t see yourself dating him. But then you really don’t have a good answer for the follow-up question; you think you do, but you don’t, because you ask the same question yourself in a different form all the time.

Here’s that question, and you need to think about it in solitude, when you’re not under emotional pressure from some guy trying to hook up with you: “Why?” Why can’t you see yourself dating him? You just admitted he’s a nice guy. Or to flip it around, you so often ask “Why can’t I find a nice guy to date?” There he is. He came to you, and you turned him away. But you said yes, time and again, to the guy who was bad to you and for you.

Life is not simply what happens to us as we are passive recipients; life is the result of our active choices. As Geddy Lee sang, “If you choose not to decide, you still have made a choice.” Your love life is the same way. It does not happen to you; it is the accumulation of the choices you have made, and will continue to be exactly that. When you want to have something better, you will need to make it for yourself, or at the very least recognize it when it comes along.

John Cusack You Ain’t

Today I want to reach out to the lonely guys. The ones who sit by themselves, pining away for the perfect girl who just hasn’t noticed how perfectly perfect he is for her, and one day they will live a perfectly perfect life together that will be just perfect. You know who you are. Chances are you think you’re this girl’s best friend; hell, she’s even told you so on more than one occasion. It just kills you a little more inside each time she does, but that’s okay, because someday she’ll see the real you, and dump that asshole boyfriend she keeps going back to. Yeah, it’s gonna happen. Any day now.

I’m here to tell you some truths you need to hear, some things you may not have heard before or maybe you have, but I say them in a way you haven’t heard them before: I say them with love in my heart, because I was you, once upon a time. Yes, my friends, I was that guy. If you don’t believe me I can provide more than a few character witnesses, but suffice to say I had my angsty teenage moments that stretched into years, and I finally found the cure.

Here’s what I want you to do: put down the half-caff latte. Step away from the copy of “Say Anything”. Drop the composition notebook full of shitty love poetry that you refuse to show to anyone anyway because “they just don’t understand you”. Understand this: you are not John Cusack, and life is not a romantic comedy. Two hours from now you will still be lonely, she will still be with him, and nothing will be different.

Now here are some of the unhelpful things you may be used to hearing, along with the typical responses (which happen internally more often than not):

Them: “You just need to be yourself.”

You: “Who else am I?”

Them: “You just need some confidence.”

You: “How am I supposed to do that?”

Them: “You’ll find the right girl… eventually.”

You: “When?”

I’m going to address these one at a time, as they are generally a mix of (as you have guessed by now) hopeful optimism and outright deception. Let’s start from the top. First off, who you need to be depends on what you want. If you keep getting rejected time and again by women, maybe “being yourself” shouldn’t be the top of your priority list. Instead, consider being somebody else. For instance, consider being someone who doesn’t come across as creepy. Also, being someone who has a job, doesn’t live with his parents, owns a car, understands basic hygiene, and has some concept of social graces can do wonders for you. Assuming you already have all of these going for you, you can move on to the next item on the list.

Confidence. Ah, that old canard. Maybe the problem isn’t confidence but communication skills. Here’s a phrase to practice while looking in the mirror: “Yes, actually.” Use this phrase the next time the girl who thinks you’re “best friends” asks something like “Are you asking me out?” or “Did you think this was a date?” or “Wait, are you straight?” You’ll be amazed at how quickly it will change the dynamic of your relationship. Most of the time it will end your relationship, but at least you will be confident about where you stand on getting a date with her. Ever. Oh, and while you’re looking in the mirror, how about comparing your wardrobe to that “asshole” she’s dating? Is he wearing the same kind of clothes now that he was wearing in the seventh grade? Are you? If the answer to one of those questions was “yes”, I bet I can guess which one. (Unless he’s a hipster. If she’s dating a hipster she deserves him.)

Finally, you’ll meet the right girl when you stop chasing after the wrong ones. Everybody has heard that women can smell desperation, but nobody has any idea what that means. Well, lucky you, I’m going to give you a little hint. WOMEN ARE NOT STUPID. If a woman sees you panting after every other woman around and asking them all out, getting shot down by each in turn before you deign to ask her out, do you really think she’s going to be grateful you finally got around to her? Conversely, if you hang on her every word, doing everything she asks of you all the time in the hopes she may grace you with just a morsel of her attention, why should she give a damn about you?

So what do all these things have in common? Respect. Respect for yourself, and respect for the woman you want to have in your life. When you respect yourself enough to hold yourself to that higher standard, others will see it and want you for who you are. When you respect others enough to clearly communicate your wants and needs without being needy and without treating them like objects or simply placeholders, you come across as confident. And when you see women as intelligent partners in meaningful relationships, not simple conquests or objects of worship, the right girl will find you.

Mine did.