Part 2: I Proposed to My Girlfriend on Top of a Mountain Pass in Colorado After a 500-Mile Ride. She Said Yes. Three Months Later, on a Cold Tuesday Night in Our Kitchen, She Told Me Something I Have Not Stopped Thinking About
I had started planning the proposal in January of 2024.
I had decided, sitting at my desk on a snowy Wednesday afternoon at the small contracting office, that I was going to ask Eden to marry me sometime in the summer.
I had decided two things on that Wednesday.
The first was that I was going to do it on a motorcycle trip. Specifically, on the kind of long Front Range loop ride we had taken together at least once every summer since 2018 — the kind of ride that involved leaving Fort Collins on a Friday morning, riding south through the foothills, picking up the high country roads through the central Colorado mountains, spending two nights at a small bed-and-breakfast in Aspen or Telluride or Crested Butte, and riding home on Sunday afternoon. We had done that loop, with small variations, six different summers in seven years.
The second was that I was going to do it on Independence Pass.
Independence Pass is a high mountain pass on Colorado State Highway 82 between Twin Lakes and Aspen. The summit sits at 12,095 feet — making it the second-highest paved mountain pass in Colorado. The road is closed in winter and opens for a short summer riding season, usually from late May through early November. The pass is, by any measure I have applied to mountain roads in the western United States, one of the ten most beautiful motorcycle rides in the country. The summit pullout has a small interpretive area with a plaque, a short paved walkway, and a stunning panoramic view of the Sawatch Range, the Twin Lakes valley to the east, and the Roaring Fork valley to the west.
Eden and I had ridden Independence Pass together exactly once before — on a Saturday afternoon in July of 2019. We had stopped at the summit pullout. We had taken pictures. She had told me, on the way down the west side toward Aspen, that it had been the most beautiful place she had ever been on the back of a bike.
I had been carrying that sentence in my chest for five years by January of 2024.
I had decided, sitting at my desk that snowy Wednesday afternoon, that I was going to take her back to that exact pullout. On a Sunday afternoon. On the way home from a long Front Range loop. With the ring in my pocket and the late summer light catching the Sawatch Range exactly the way it had in 2019.
I had picked the date by mid-February. The trip would happen the first weekend in August. We would leave Friday August 2nd, 2024, ride south through Buena Vista, spend Friday night in Salida, ride west across Monarch Pass on Saturday morning, spend Saturday night in Aspen, and ride home over Independence Pass on Sunday August 4th, 2024.
I had picked the ring by late March. I had bought it from a small jewelry store in Old Town Fort Collins that I had been a customer of for twelve years. The ring was a simple solitaire — a 1.05-carat round-cut diamond on a clean platinum band — that had cost me $7,840. I had paid in cash from a small savings account I had been building specifically for this purpose since 2021. The ring had been in a small velvet box in the locked top drawer of my desk at the contracting office from late March until late July.
I had told three brothers in my chapter — Trace McAllister, Donny Mendelsohn, and Carl Holzwarth — about my plan in late April. I had told them the plan because I needed at least one of them to know in case I died on the trip down without ever proposing. I had wanted, specifically, for someone in the world to know what I had been planning so that if something happened to me on the road, the ring would not be a mystery in the back of a drawer.
The three brothers had agreed to keep the secret.
They had, by every reasonable account I have, kept it.
What none of us had factored in was that in late July of 2024 — about two weeks before the trip — I would do the thing that I now realize was the small unforced error that gave the entire game away.
I had moved the ring out of the locked top drawer of my desk at the contracting office.
I had moved it home.
I had moved it home because I had been worried about leaving the ring at the office over the weekend of the trip. The office was in a strip mall on the south side of Fort Collins. It had a decent alarm system. It had not, in twelve years, been broken into. But the idea of riding to Aspen with the ring still locked in my office desk three hundred miles away — and not in my saddlebag, where it would be traveling with me — had not made sense to me.
So I had moved it home.
I had moved it home on Tuesday July 30th, 2024 — three days before the trip.
I had put it, that evening, in the small inner zip pocket of the right-side saddlebag of my Road Glide.
I had not, at any point in those three days, told Eden the ring was in the saddlebag.
I had also not, at any point in those three days, considered the possibility that Eden might have any reason to look in the saddlebag.
That had been, looking back, an unforced error.
Eden, I would learn three months later, had a very simple and very loving reason for opening the right-side saddlebag of my Road Glide on the morning of Friday August 2nd, 2024 — the day we left for the trip — about three hours before we rolled out of our driveway.
She had been packing for both of us.
I had asked her to do it because I had been on a small jobsite that morning. She had agreed, the way she always agreed, with the calm efficiency of a senior physical therapist who knew how to pack for a three-day motorcycle trip in less time than it takes most people to make a sandwich.
She had been packing my saddlebags for me.
She had opened the right-side saddlebag.
She had begun loading my clean t-shirts and underwear into the main compartment.
She had, while doing that, noticed a small lump in the inner zip pocket of the bag.
She had, as one does when packing for a partner, unzipped the pocket to check what was in it.
She had found the small velvet box.
She had opened it.
She had seen the ring.
She had — and this is the part of the story she told me three months later in our kitchen, that I want to be careful about because it is the heart of what this entire story is actually about — sat on the kitchen floor next to my open saddlebag for about twelve minutes with the ring in her hand and tried to decide what to do about it.
She had had three options.
The first option had been to confront me when I got home from the jobsite. To tell me she had found the ring. To ask me whether I had been planning to propose. To clear it up before we left for the trip and not have a secret between us.
The second option had been to pretend nothing had happened, leave the ring in the bag, say nothing, and let me propose on Sunday on Independence Pass — knowing the entire time that I was about to.
The third option had been to discreetly take the ring out of my saddlebag, hide it somewhere in our house, and force me to either notice the ring was missing before we left, or after. Both of which would have been small minor disasters that would have, by her own assessment, ruined the trip in a number of different ways.
She had thought about it for twelve minutes.
She had picked option two.
She had put the ring carefully back in the inner zip pocket.
She had zipped the pocket closed.
She had finished packing the saddlebag.
She had gone about her morning.
When I had gotten home at 11:47 a.m. that Friday, she had been on the front porch with her riding gear on and a small smile on her face that I had, at the time, attributed to her happy excitement about the trip.
I now know it was the small smile of a woman who had decided, four days before I went down on one knee, that she was going to give me the moment I had been planning for seven months without telling me she had figured it out.
She had given me three days of road, two nights in beautiful mountain bed-and-breakfasts, and an unforgettable Sunday afternoon on Independence Pass — and at no point in any of it had she let on, by word, gesture, or facial expression, that she knew what was coming.
She had, on Sunday afternoon at the summit pullout when I had dropped to one knee, performed the absolute most convincing surprise reaction of her life.
She had cried real tears.
She had said real “yes.”
She had hugged me with real arms.
She had not, in any visible way, been faking any of it.
She had, by her own gentle correction in our kitchen three months later, simply been allowing herself to feel what she was already feeling about a man she had already said yes to in her heart four days earlier.
She had not been performing.
She had been, in her own quiet careful way, letting me have the moment.
That is, in three sentences, the whole story.
The next four sections are about what that meant — and what it took me three months and one Tuesday night in our kitchen to begin to understand about the woman I was going to marry.
I want to tell you about Sunday August 4th, 2024.
We had ridden out of Aspen at 9:47 a.m. The morning had been clear, cold at altitude, and by every measurement of my own state of mind that morning — the most carefully prepared moment of my life. I had gotten up at 5:00 a.m. I had checked the ring three times before we left the bed-and-breakfast. I had double-checked the ring in the inner zip pocket of the right-side saddlebag while Eden was in the shower. The ring was where it had been since Tuesday July 30th. I had been completely unaware that the ring had also, at some point on Friday morning between 8:14 a.m. and 11:47 a.m., been held by Eden on our kitchen floor in Fort Collins for about twelve minutes.
I had been, by every measurement, completely confident in my plan.
We had ridden up Highway 82 from Aspen toward the summit. The road climbs from about 7,900 feet at Aspen to 12,095 feet at the summit pullout — a vertical climb of just over 4,000 feet in about twenty miles of pavement. The road switchbacks through aspen groves and high alpine tundra and crosses Lincoln Creek and finally breaks out above the tree line at about 11,500 feet.
Eden had been quiet on the back of the bike. I had assumed it was the high altitude. People sometimes go quiet at altitude. The oxygen at 12,000 feet is about 60% of what it is at sea level. Conversations slow down. People become more contemplative.
I had been completely unaware that her quiet was the quiet of a woman who knew — and had known for four days — that the man she was riding behind was going to ask her to marry him within the next forty-five minutes.
We had pulled into the summit pullout at 10:34 a.m.
The pullout is a small paved area off the right side of the road at the absolute summit of the pass. There is a small interpretive plaque, a short paved walkway, a wooden interpretive sign about the alpine ecosystem, and a panoramic view of the Sawatch Range to the east and the Roaring Fork valley to the west. On a clear August morning, you can see, from the summit pullout, parts of three different mountain ranges, four different fourteen-thousand-foot peaks, and the small bright blue pinprick of Twin Lakes about fifteen air miles to the southeast.
It is one of the most beautiful places I have ever stood in my life.
Eden had taken her helmet off. She had put her braid back together. She had walked, with me, to the wooden interpretive sign. She had put her hand on the railing. She had looked east.
The light had been exactly what I had remembered from July of 2019. The cold high-altitude sunlight catching the Sawatch Range. The pale blue alpine sky with high thin cirrus clouds. The wind, soft at the summit, moving the small alpine flowers along the walkway.
I had not, in that moment, considered for even a second that Eden might already know what I was about to do.
I had said, “Eden.”
She had turned around.
I had gone down on one knee.
I had pulled the small velvet box out of the inner pocket of my riding jacket — where I had moved it from the saddlebag at the bed-and-breakfast that morning while she was in the shower.
I had opened the box.
I had said the words I had been rehearsing, on and off, for seven months. I am not going to give you all of them. They were the words a thirty-seven-year-old man says to the woman he has loved for seven years when he wants to spend the rest of his life with her. They were specific to her. They referenced moments. They referenced the steadiness she had brought to my life. They were, by any measure, the most prepared and most heartfelt one hundred and twenty seconds of speech I have ever produced.
I had ended with the question.
“Eden Whitcombe. Will you marry me.”
She had stood there for about three seconds.
She had — by her own account three months later — felt all the feelings of an actual yes, in real time, in that exact moment, even though she had already mentally said yes four days earlier on our kitchen floor.
She had said, “Yes, Wesley. Yes.”
She had cried.
I had cried.
I had put the ring on her finger.
I had stood up.
I had hugged her.
We had stood at the summit pullout for about ten minutes.
A small cluster of other tourists — three different groups who had been at the pullout when we arrived — had figured out, from about thirty feet away, what was happening. They had quietly waited. After we had stood up and hugged, one of the women in one of the tourist groups had walked over and asked, very politely, if she could take a photograph of us.
I had said yes.
She had taken three photographs on my phone. They are, today, on the wall of our small ranch house off Vine Drive in Fort Collins. They are the first three photographs in our wedding album. The album opens with them.
We had ridden back down to Twin Lakes for lunch.
We had ridden home through Buena Vista that afternoon.
We had pulled into our driveway at 7:14 p.m. on the evening of Sunday August 4th, 2024.
We had been engaged for eight hours and forty minutes.
I had no idea, at 7:14 p.m. that Sunday evening, that my fiancée had been engaged in her own heart for four days and eight hours.
I would not figure it out for another three months.
I want to tell you what happened on Tuesday November 19th, 2024.
It had been a cold Tuesday evening. We had been engaged for fifteen weeks. Eden had been wearing the ring continuously since the Sunday of the proposal. We had set our wedding date for June 14th, 2025. We had booked the small mountain lodge near Estes Park. We had been, by any measure, completely happy.
I had gotten home from the office at 6:47 p.m. Eden had been in the kitchen making a small pasta dinner. We had sat down to eat at 7:14 p.m.
About twenty minutes into dinner, Eden had set her fork down.
She had said, “Wesley. There is something I want to tell you. It has been on my mind for a long time. I want to tell you tonight. Will you let me tell you the whole thing before you say anything?”
I had said, “Of course, baby.”
She had taken a small sip of water.
She had said, “Wesley. I knew you were going to propose on the trip. I knew before we left.”
I had set my own fork down.
She had told me everything.
About finding the ring while packing the saddlebag on Friday morning. About sitting on the kitchen floor for twelve minutes with the ring in her hand. About the three options. About picking option two.
I had not, for about thirty seconds, said anything.
Then I had said, “Eden. Why.”
She had said, “Wesley. Why what.”
I had said, “Eden. Why didn’t you tell me. Either before the trip or after the trip. Why did you let me — why did you let me think I had pulled off the surprise of a lifetime.”
She had thought about it for a long moment.
She had said, “Wesley. Because that was not the surprise.”
I had said, “Eden. What.”
She had said, “Wesley. Sit with this for a second. The surprise of an engagement is not whether one of the two people knows it is coming. Most women, by the time their boyfriends actually propose, have figured it out within at least a couple of weeks of advance notice. There are signals. There are conversations. There are jewelry-store search histories on shared family computers. The exact day and hour are sometimes a surprise. The fact of the proposal almost never is.”
She had paused.
She had said, “Wesley. The surprise is not whether the woman knows. The surprise is whether she is going to say yes. The surprise — the actual question, the actual moment, the actual breath-held three seconds at the top of Independence Pass — is the man asking and the woman answering. That is the moment. That is what matters. The fact that I had four days to think about it instead of zero seconds did not change my answer. I had been going to say yes from the day you told me on our second date that you would not hide a third of your life from me. I had been going to say yes from the day I met your chapter brothers at the cookout. I had been going to say yes from every road trip we have ever taken. The four days between Friday and Sunday changed nothing about my answer. They only changed how prepared I was to feel it in real time when you actually asked.”
She had paused again.
She had said, “Wesley. I want to tell you something that may sound counterintuitive. The four days were a gift. To me. From me. I had known for four days, with absolute certainty, that you were going to ask me to marry you. I had spent those four days sitting with what that meant. I had spent those four days watching you eat pancakes at the bed-and-breakfast in Salida and noticing the way you held your coffee cup. I had spent those four days behind you on the bike across Monarch Pass thinking about the next forty years of mornings I was going to wake up next to you. I had spent those four days, in private, falling more in love with the man I was about to officially say yes to.”
She had paused.
She had said, “Wesley. The reason I did not tell you is because the moment you went down on one knee at the summit pullout was, for both of us, a real moment. It was not a performance for me. It was the absolute opposite of a performance. It was the moment a question I had already answered in my heart became a question I got to answer with my voice. That is what proposals are. The voice answer. The witnessed answer. The ring-on-the-finger answer. None of which I had done yet. None of which I was going to deny you, or me, or us, just because I had four days of advance internal processing time.”
She had paused.
She had said, “Wesley. The reason I am telling you tonight, fifteen weeks later, is because I do not want our marriage to start with a small secret between us. I have been carrying it for fifteen weeks. I do not want to carry it anymore. I love you. I am marrying you in seven months. I want you to know everything. Including that I knew for four days. Including that I kept it. Including that I did it on purpose because I love you and because I wanted you to have the moment you had been planning for seven months.”
She had stopped talking.
She had looked at me.
I had not, for about a minute and a half, been able to speak.
Then I had said, “Eden. I — I do not know what to say.”
She had said, “Wesley. You do not have to say anything tonight. I just wanted you to know.”
I had said, “Eden. The four days. What did you do. What was that like for you.”
She had said, “Wesley. I did mostly the same thing I always do. I worked. I went to the clinic. I saw my patients. I ate dinner with you. I went to bed beside you. The only thing I did differently was I started, in private, drafting how I was going to want to call my mother after you proposed. I started thinking about how I was going to want to tell my sister. I started, very quietly, in my own head, planning a few small things that I was going to want to do in the seventy-two hours after you asked me. I gave myself those four days as a kind of running start.”
She had paused.
She had said, “Wesley. I think the four days made me a better fiancée in the first ninety-six hours after you proposed. I had, by then, already done the thinking. I could just be with you. I could just enjoy it. I could just be present. The four days were not a deception. They were a preparation. I was preparing to be the best version of the woman who said yes.”
I had not, for another long minute, been able to speak.
Then I had stood up from the kitchen table.
I had walked around to her side of the table.
I had pulled her up out of her chair.
I had hugged her for a long time.
I had said, into her hair, “Eden. I love you. I love you so much.”
She had said, “Wesley. I know, baby. I love you too.”
I had said, “Eden. The four days were a gift. To me. From you. I just did not know it for fifteen weeks.”
She had said, “Wesley. You know it now.”
I had said, “Yeah, baby. I know it now.”
We had stood in the kitchen for about ten more minutes.
We had finished dinner.
We had gone to bed.
I have not, in the year since, ever stopped thinking about that conversation.
I think about it almost every day.
I want to tell you the small detail Eden told me at the kitchen table that I have not told you yet.
She had told me, after the main story, one small additional thing.
She had said, “Wesley. There is one more thing. Do you remember the Saturday afternoon I went to the chapter cookout with you in late June, about five weeks before the trip?”
I had said, “Yes.”
She had said, “Wesley. While you were grilling, I was sitting on the picnic bench with Trace McAllister. We were talking about the weather. About summer trips. About nothing in particular.”
She had paused.
She had said, “Wesley. Trace said one sentence to me at that picnic that I have not told you about. He said, ‘Eden. Wesley is a careful man. When the time comes, he will be ready. You should be ready too.'”
She had paused.
She had said, “Wesley. He did not say what for. He did not name it. He just — he just gave me one careful sentence, in case I wanted it. He told me, in the way a brother sometimes tells the woman his brother loves something the brother cannot tell her himself. I had not, until that sentence, really considered that you might be planning a specific moment. After that sentence, I had started, very quietly, watching for it.”
She had paused.
She had said, “Wesley. I am not telling you this because I am angry at Trace. I am telling you this because Trace gave me five weeks of advance preparation time. The four days at the end were just the final confirmation. I had already, by the time I found the ring on the kitchen floor on Friday morning, been preparing for five weeks.”
I had said, “Eden. Are you angry at Trace.”
She had said, “Wesley. No. I am grateful to Trace. Trace knew the difference between giving away the secret and giving the partner of his chapter brother a small head start. He did not tell me anything specific. He just told me to be ready. He gave me the gift of preparation without giving away your moment. That is the most careful thing a chapter brother could have done for both of us.”
I had said, “Eden. I am — I am going to thank Trace tomorrow.”
She had said, “Wesley. He does not need thanks. He just needs to know that the brother he was protecting both ends of has figured out what he did.”
I had called Trace the next day.
I had told him I had figured out what he had said to Eden at the cookout in late June.
He had been quiet on the phone for about ten seconds.
Then he had said, “Wes. Brother. I did the math. I figured a woman like Eden was probably going to find the ring before you got to the pass. I figured if she had a few weeks of warning to think about it, she would handle it in the way she handled it. I did not want her to be ambushed. I did not want her to feel like she was accepting a proposal she had not been allowed to think about. I gave her one sentence. I gave you eight months of the planning. I figured that was a fair split.”
I had said, “Trace. I owe you.”
He had said, “Wes. You don’t owe me anything. Just take care of her. She is the steadiest woman I have ever met.”
I had said, “I will, brother.”
I had hung up.
That is the entire story.
The brother who set up the head start.
The fiancée who used the head start.
The proposer who did not figure any of it out for fifteen weeks.
The woman who waited fifteen weeks to tell him because she did not want to carry a secret into a marriage.
Eden and I were married on June 14th, 2025, at a small mountain lodge near Estes Park, Colorado.
Trace McAllister was one of the four chapter brothers who stood up with me as groomsmen.
In my wedding speech at the reception, I told the story of the four days. I had asked Eden’s permission first. She had said yes. I had told the assembled guests — about ninety-five people — about how Eden had found the ring on a Friday morning, sat on the kitchen floor for twelve minutes, and decided to give me the moment.
I had ended the speech with the line that I think summarizes everything about the woman I had married.
I had said, “Eden has been doing this for me for eight years. The four days at the top of Independence Pass were not a one-time thing. The four days were a whole way of loving somebody. The four days were exactly the kind of patient careful generosity she has shown me every single day we have been together. The four days were not the exception. The four days were the rule. I am marrying the rule.”
She had cried.
I had cried.
The brothers had cheered.
We are, today, almost six months married.
I am still, in November of 2025, thinking about the four days.
I will, by my own honest assessment, be thinking about them for the rest of my life.
I will tell you the smallest version of this story, in case you skipped to the end.
I had spent seven months planning the perfect proposal for my girlfriend on the top of Independence Pass in Colorado.
I had carried the ring for four months.
I had moved it to my saddlebag three days before we left.
She had found the ring while packing for me on the morning we left.
She had sat on our kitchen floor for twelve minutes, weighed three options, and decided to give me the moment.
She had ridden 500 miles behind me over the next three days, slept beside me in two mountain bed-and-breakfasts, and said yes at 10:47 a.m. on Sunday morning at the summit pullout — with three real tears, a real yes, and a real hug.
She had told me about the four days at our kitchen table on a Tuesday night fifteen weeks later because she did not want to carry a secret into our marriage.
She had also told me, in the same conversation, about a single sentence my chapter brother Trace McAllister had said to her at a chapter cookout five weeks before the trip — a sentence designed to give her advance preparation without giving away the moment.
I had been the only one of the three of us who had not known, at the moment of the proposal, that the proposal was coming.
I had also been the only one who had needed to not know.
I had needed to ask the question, on one knee, at 12,095 feet, with the late summer light catching the Sawatch Range, exactly the way I had pictured it for seven months.
She had given me that.
She had given it to me on purpose.
She had given it to me even though she could have taken it away.
That is the entire story.
That is the woman I married.
I will be loving her for the rest of my life.
If this story moved you — follow the page. There are more men out there who spent seven months planning proposals their girlfriends figured out in twelve minutes on a kitchen floor. More women who decided to give their men the moment anyway. More chapter brothers who said one careful sentence at a cookout. More four-day gifts that nobody knows about for fifteen weeks. There are more stories the world doesn’t see — and I will keep telling them as long as someone keeps reading.
