I have received news from your unlikely acquaintance, Mr. Washington Irving, about your recent experiences and ambitions in the art of love. Mr. Irving told me your story and I decided I must take it upon myself to write you and give you some vital "wooing" advice you obviously are in so desperate need of. I pray that you will read and consider my words carefully.
In the short time that I have come to know you Mr. Crane, I have made some very distinct observations about your character. I shall start with the good. You are learned man Mr. Crane. A man who possesses great wealth in knowledge and understanding. The people adore your stories and recitations of poetry. It is a skill in which you have no rival in our small town of Sleepy Hollow. I've seen and heard the way people flock to you when they desire an adventure, a thrill, or a story of suspense. This same skill is displayed in your wonderful voice. There is not one among our bretheren who does not love to listen to you sing praises to our Lord Mr. Crane. You have a strength for conversing with others, when your focus is not on yourself. This strength is also found in your ability to transfer your audience into your tale or song. This is a quality I, among many others, deeply admire in you Mr. Crane. You are most compliant with those around you. I have rarely seen you take up an argument or fail to complete a task someone has asked you to do. That type of servitude is admirable, when completed for the right reasons Mr. Crane (not out of fear)... but we shall come back to that in a bit. Please know, Mr. Crane that I did search ever so deeply into my knowledge of your person to discover your praiseworthy qualities. I know you shall find that my belief in the man you could be, is much stronger than the man I find you to be currently.
I'm afraid Mr. Crane, here is where I must point out to you your flaws and weaknesses. Be attentive in my harsh criticism, because it is for your benefit by my knowledge of your hope to win the heart of the Lady Katrina Van Tassel.
First, Mr. Crane you are a glutton. You spend more time focused on food and your stomach than the lives of those around you. I have heard how you are unable to purchase enough food to sustain yourself and therefore are forced to live with the families of your students. DISGRACEFUL, Mr. Crane! Do you really believe the Lady Katrina would ever want to marry a man who eats more than he sleeps, has no home, wastes his income, and is forced to live completely of the charity others to survive? I assure you she would never! Your first duty Mr. Crane would be to train yourself in the fruit of self-discipline and moderation! Food is worth nothing in this life man! Yes, three meals a day and tea time is vital for survival in this world, but beyond that there should be no such unsustainable value in food. This carries over in your desire for wealth in order to fill your stomach. You are weak Mr. Crane. In the face of all women you ought to be ashamed of your greedy obsession with wealth and the luxury you believe it brings. You are sorely mistaken man. It will never be enough Mr. Crane. You will die having gained wealth, but having lost everything that is of value to life. Those people you loathe now for looking down on you, you would sell out to become like them! Ichabod, I will not let you continue down this road of destruction! Our Holy Bible tells us that money is the root of all evil. Do not let yourself be tempted by the pleasures you feel wealth could bring you. It will ultimately destroy you. Besides Mr. Crane, no woman wants a greedy fat man for a husband, of that I can assure you.
I admire your belief in discipline among your students, but sir, you must express more grace and compassion instead of wrath. Man, we are to be like Christ during our pursuits in this life. Women want men they feel safe and secure with. Women swoon for men who carry compassion and love in their hearts. You have let your heart grow bitter and angry Mr. Crane. No longer! Bestow mercy, forgiveness, and love on the people around you. When you treat others with that Christ-like attitude everyone will notice, especially Lady Katrina. And you man, will be better off for it.
Secondly, you will find that not spending so much money on frivolous things you will be able to improve yourself in numerous valuable ways. You could get yourself some fine and proper clothes for a man of your station... not those bulky, baggy drags I saw you wearing last week. They lower you in the eyes of others Mr. Crane. Not only that, but once again, Lady Katrina shall be observing your dress in order to determine your stewardship. If you can not care for yourself properly sir, how she expect you to care for her? Buy some fitted clothes Ichabod. Wash and have your hair cut so that it no longer looks and smells like a rat's nest. Ladies are most perceptive about these types of things... as are people of higher stations whom you know look down on you for your state of dress. Do not purchase anything too expensive, just clothes befitting and intellectual, intelligent gentleman like yourself.
Speaking of gentleman sir. I am going to give you the most important lesson of this letter. BE A MAN. Lady Katrina desires to find a MAN to become her husband. Yes, yes, sir, I know age-wise you are very much a man. Yet sir, in your physicality, skills, and mannerisms I find you little more than a cranky, spoiled, inconsiderate, school-boy. BE A MAN! Think of the great men of old! You are learned Mr. Crane: King David, Sampson, or the legendary King Arthur and his knights, Robin Hood... the Jamestown adventurer John Smith, or even our own current General George Washington! What do all these men have in common? COURAGE, MAN! These men became great because of their extreme courage! They did not give up in face of adversity. They were and still are great leaders of our time. Women desire a leader. Someone to guide them through this difficult life. No more of becoming this "sniffling girl" in the nighttime Crane. Be strong and courageous! That is the true mark of man! Learn how to ride a horse properly for goodness sake Crane. No woman dreams of their knight in shining armor without a horse! Learn how to ride like a proper man! Not only will it be of great benefit to you in the long run, but it will completely transform your image in the eyes of all. Be confident and courageous in all your exploits! Lady Katrina will be at your mercy, begging for your love, if you do these things Mr. Crane.
Dear sir, I hope you realize my harshness is written in loving earnest that you would find a content and happy life with a content and happy wife. If you wish her to be the Lady Katrina, these are my suggestions on how to become the man of her, and every woman's, dreams. We've talked about what you need to stop doing, now let's discuss what you need to start doing. If you want Lady Katrina to notice you, you must make her feel valued and important. Go out of your way to compliment and surprise her. Flowers are a spectacular start (if you want to get really clever poetry and singing go a long way). Listen to what she has to say and care, Mr. Crane. Stop seeing Lady Katrina as a means to her father's money and instead seek to capture her heart, seek to know the smallest most detailed things about her. A little thoughtfulness goes a long way sir! As does patience. Dealing with any woman Mr. Crane require devotion and patience that comes only from our heavenly Lord. Don't be afraid to be honest. Being a courageous man means being honest with her in kind and comforting ways, putting yourself out there. You have much work to do Mr. Crane. Do not dally... a woman such as Lady Katrina is not likely to wait around for long.
I believe in you Mr. Crane. You have the makings of a great man in you... perhaps even a good one. You have my fondest regards and my deepest prayers as you pursue to be more like our Lord to win the heart of a lady. Times are changing Crane. A man as wise as you must know this. The war has changed everyone, some for the better, others not. Do not let your selfish ambitions or childish fears keep you from living life to the fullest. I will correspond again soon Mr. Crane as I wish to hear of your progress into true manhood.
May God bless and keep you Mr. Crane. I hope the next time we meet you shall be astride a brilliant charger looking like a whole new man with compassion in his eyes for all around him. Perhaps then the Lady Katrina will have a run for her money against myself.
Letter composed as an assignment for a university level American Literature class in response to the classic short story "The Legend of Sleepy Hollow" by Washington Irving, 1820.