The Role of the Past and the Proposal

James Anthony Ellis 
Legacy Magazine Editor

Is there a larger or more far-reaching enrollment process than that of the courtship towards marriage?

Possibly, but that is the one that comes to mind as I consider where in my life I have practiced the art of enrollment in all its nuance.

We’ll take this art form in three parts:

  1. The Past
  2. The Preparation
  3. The Proposal

(By the way, as a side note, don’t think for a second that I really knew what I was doing through any of this. I was simply living my life, listening to my heart and to reason – or not – and moving forward, sometimes hesitantly and sometimes with confidence.)


Let’s set this up first. Prior to marriage, I had many years of dating, of being lost in the unknown. At first I was completely oblivious. How does one do this? I remember the first consideration of a date – the senior prom – and how I was aghast at how much I didn’t know what to do. What to wear? How to get there? What to do on the date? What to say on a date? How to end a date? How to get through it all without throwing up?

I was so lost in this field. As a late teen and even into my early 20s, I didn’t know of any books; my folks weren’t much help, and I didn’t yet have a posse, tribe or men’s circle to draw upon.

And so I stumbled along, feeling agitated, anxiety-ridden, but asking a few gals out and getting a few dates here and there. For some unconscious reason, I got it in my head that if I just held hands or showed any affection to a female, I somehow was fully committed to her for life. Talk about anxiety! Plus, who would want to date someone like me, who held such a heavy context around just going out for some fun?

After dating through my 20s and believing I had gathered enough clarity on what I wanted, I dove into a long-term committed relationship with a woman, and even moved in with her. I was 30. I was hopeful. And I was stupid as fuck.

This was a couple years before doing the Sterling Men’s Weekend, where I learned that a man must, before marriage, REALLY know who he is as a man, recognize his terms and be willing to not compromise them. Well, short story not short enough: that relationship blew up in my face, and I was left as a shell of a man who had lost himself by giving up himself. The comeback would take over a decade.

Before doing that Sterling Weekend, pretty much all of my relationships ended in some form of heartbreak, as I had compromised myself on some level each time. After doing the Weekend, I never experienced that sort of pain again. Of course, there would be the pain of losing or missing an affectionate love in my life, but I didn’t again experience the pain of losing my soul as a man.


I was much more conscious in the dating I did after I attended that Men’s Weekend in that I knew I was actually defining myself in the process, not trying to FIND THE ONE true woman who could fulfill all my needs. I learned what I could live with, what I would not live with. I recognized the importance of being myself as a somewhat kooky, creative and freely expressive person who could utter some nonsensical whim just to get a smile or a laugh. I found out I wouldn’t be marrying a drinker, a smoker, a non-vegetarian. I also realized the vital importance of being with someone who could truly respect my boundaries and my sense of territory, in the space of my home, and in the need for a space for my creative endeavors.

I imagine this dating process was a way to enroll myself into my own vision of relationship, and my own uplifted place I could have within it.

For so many years, I was preparing myself. With all that experience under my belt, I felt I was becoming ready for a long-term relationship.

And then came Jennifer.

This is where the enrollment would arise in the form of courting.

After finding out how much we aligned on the surface topics, I came to learn how much she respected my time and space to my creative work. She fully supported my writing time. She was proud and praising of what I wrote, or produced in film. But the most important thing – she knew that my time in the office as well as the physical space of my office was sacred to me. And she honored that.

This was huge.

I’ve never had a woman who would so hold my creative space that way. Other women seemed to want to compete with my creative purpose and the time it would take to complete projects. Other women fought for time and space with me. Other women thought they could pit themselves against my higher purpose as a man, and win.

Never could a woman ever really win that battle.

With the stress of that battle removed, it made it so much easier to court Jennifer and have fun in the process.

Enrollment was natural here. I could just be me and express it towards her, without sales, without manipulation, without coercion, without thinking I had to fool her into thinking I was something I was not.

Out would come the poetry for her, out would come the creative ideas to surprise her, out would come the innovative and interesting ways to make her happy. No problem!

But I didn’t have to think about it or plan it out. I would have an idea – a fun outing, a surprise gift, a piece of prose – and I would follow through.

This was the courting phase, where the enrollment would be such a flow.

It flowed all the way up to the ultimate act of enrollment within a relationship…


By the time, the proposal comes along for men, I’m thinking we’ve pretty much done all the enrolling that would be needed. Well, except for those dumb dudes who think they got it all sewn up and then embarrass themselves at a ballpark with a rejection scene on the jumbo screen.

For those ready for success with the proposal, it’s like all the preparation has been put in place. It’s like the rehearsal before an opening night of a play. It’s like all the practice for the big sports game day, where you just go through the basic motions, even knowing the first 10 plays. It’s like the movie-maker who works so hard on the story board, that the rest is as easy and following through on the clear vision.

I was ready to propose. And so I did it as I would want to do anything related to my relationship: with a creative flair.

I set it all up. I first made my way around town, enrolling others into my vision, traveling to the seven most popular places Jennifer and I most often frequented throughout San Diego. I set up a contact there to hold a few Scrabble tiles in their possession, so that when Jennifer arrived, they could hand her these lettered tiles. The way Jennifer got from place to place was through a Treasure Hunt, wherein each location would be found in a clue, written in rhyming prose.

She read a clue and found her way to Doggie-dos on Jackson Drive, where Brianna would have a few tiles to offer. The next clue would take her to Citibank where Patty offered up more tiles. Then onto the dog sitters, then onto the Mexican restaurant, and on and on.

The final location was one of our favorite San Diego spots we would visit every New Year’s Day to vision for the year: the stairs down to the rocky beach at the end of Sunset Cliffs Boulevard. The final Scrabble tiles she gathered here. And it was here I invited her to spell out the words. I was afraid she would have already figured it out along our journey, but she played right along with the game.

As she worked out the letters to spell out the phrase, I found myself getting really nervous. Oh my, she is going to figure it out, and then it will really be out there! I was so into the planning and creative phases, that I forgot we would ultimately be lead to the defining moment.

She was definitely surprised, as the video shows.

She was definitely happy.

And yes, she was definitely enrolled.

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James Anthony Ellis is an award-winning playwright, journalist and filmmaker, who is the author of eight books, including the men-focused “The Honor Book” available HERE.

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