It was wonderful to read about your pure and God-honouring friendship with this woman. It is so refreshing when a man and a woman choose to keep Christ at the centre of their lives. And it sounds like you know in your heart what you are seeking with this woman. Here is an important question for you to ponder before you make the step of "transforming" your relationship from friendship to romance. Are you both at a stage in life where marriage would be a real option? (age, stage, employment, etc.)
If you are, and you feel God is calling you into a courtship with this woman, then I would recommend that you take the initiative and propose the idea of a courtship to her.
Here are a few things to consider as a relationship transforms from friendship to courtship:
Because of the nature of intimacy that you already share as friends, it is possible that the courtship could move very quickly — either into discerning marriage or calling it off (because romance just won't feel natural with each other). Either outcome is okay — remember the purpose of a courtship is to discern whether or not you are called to marriage.
If you discern that you are not called to marriage — the courtship has not failed. And if you do decide to call off the courtship, you should be able to still be friends . . . though I would recommend at that point you back off from the status of "best friends". Being best friends with a woman whom you are not going to marry will certainly hinder you from entering into a courtship and marriage with another woman. I can tell you that I would not be comfortable with my husband having another woman as his best friend!!! We both have opposite-sex friends. But not as confidants whom we turn to for specific support, as one would a “best friend”. You need to leave room for your future wife to have that place of honour in your life.
Your courtship may lead you to discerning marriage. Be sure to not allow haste in this matter. By that I mean, take time to actually pray for guidance and wisdom in this matter. Don't just make it a done-deal the moment you enter into the courtship. (This is going to be a real temptation.) You may feel right away in your hearts to follow the course of marriage; however, you should take some time to test those feelings. Don't just automatically call an engagement. Let your relationship breath for a while as you pray about that decision and grow together in a new way.
Don't allow your heads to so rule over your hearts that you forget romance. As you transform a relationship that you have guarded against romance into romance — don't forget to be romantic! As the man, you need to take leadership in the area of romance in a courtship. Be creative, be fun, be spontaneous at times — but allow her the benefit of feeling and knowing your affection. (This can be in words or by actions — or both, as you see fit.) A woman needs to feel cherished — not just as a friend, but as your one and only love — if she is going to make the decision to commit her life to you in marriage.
Set guidelines in your relationship from the very start to keep your physical intimacy in check. You've got a beautiful, pure and holy relationship. Don't allow the temptation of physical intimacy to spoil what you've worked so hard to achieve these past five years! Decide on what will be acceptable expressions of physical affection and what you plan to reserve for marriage. As I'm sure you are aware, some couples decide to save their first kiss for marriage. This isn't required or necessary — but it is really awesome when a couple does go through with it. These couples give a truly inspiring and refreshing witness to all around them, but it richly blesses them as well. They know they've saved it all for each other!!! (Even when one of them has a past.) The practice of self-discipline and self-denial through the courtship and engagement only serves to heighten their anticipation of marital joy!
Also, be sure to read up on courtship and Christian marriage. Here are a few great resources:
Josh Harris' books: I Kissed Dating Goodbye and Boy Meets Girl: Say Hello to Courtship. I loved both of these books and couldn't recommend them more!
Steve Wood's books: ABCs of Finding a Good Wife and ABCs of Finding a Good Husband have some excellent ideas for you both to ponder as you discern marriage.
Christopher West's book: Good News About Sex and Marriage: Answers to Your Honest Questions about Catholic Teaching is and absolute must-read for ever couple entering into marriage!!! If you want to see and understand the beauty of God's plan for us in marriage and then live it out in your life -- this book will take you there. His audio resources are also extremely good. Chris West's work is based on Pope John Paul II's Theology of the Body which is so totally life-giving . . . it'll blow you away! And Chris presents it with such humour, energy and passion!
Finally, and most humbly, I recommend my own novel, Arms of Love, if you have not already read it. This is the fictional account of a young man and woman as they journey through a courtship relationship. As you enter into the lives of the characters, you discover the depth and beauty of the Christian meaning of love and marriage. Because it is fiction it is an easy-read, engaging and compelling as a story. Though just a novel so many people have told me that they came away from it changed. It would seem that the Holy Spirit has been working through the humble instrument of a novel to reveal to men and women (of all ages) truth and to inspire in them hope and purity!
I hope these ideas help you as you discern your relationship with this young woman and your call to marriage. I applaud your perseverance in maintaining a pure, holy and God-honouring friendship with her for so long. I pray that if you are called into courtship and marriage that you will be blessed to live out a pure, holy and God-glorifying romance in your lives!!!
I would welcome hearing back from you about how things turn out. I am collecting real-life stories of people's relationships that I can include in my Courtship Now E-Letters. I also like to share real stories with people when I go around speaking on purity, chastity, courtship and marriage. (I always guard anonymity and privacy with the highest priority!
We remember our readers each day in our prayers. I ask you to remember me, my family and this ministry of promoting purity in your prayers!
In His Most Holy Name,