Sometimes you just get lucky. Really lucky. The day I proposed to Megan was one of those lucky days that we will both remember forever.
Let’s Rewind
We had been planning our three week trip to Europe for about a year, and we had talked about it for longer. It was 2005, Megan had just graduated from law school and taken the bar, and she had a month off before starting her new career.
When she started her new job in September, I was going back to school full time, so I took August off as well as our thoughts were that we wouldn’t have another chance to travel for that long until we retired. We had been together for 5 years, living together for 3. It was no surprise to Megan, our families, and our friends that I was most likely going to ask her to marry me at some point during our trip.
There was no plan
I’m a planner. I’m very organized when it comes to planning things out, whether it be trips, nights out, cleaning the house, whatever. I like to have a plan together, and I LOVE lists. So one would think I would have had a plan together for what was to be the most important moment in my life up until that point. I was going to ask the woman I love to spend the rest of her life with me, while we were in a foreign country, so surely I knew where and when I was going to do this, right?
Even though it was only 6 short years ago, I was a total noob when it came to international travel. We had been to Mexico once, in an all inclusive resort, and that was the extent of my experience. So I didn’t want to plan something without being able to envision it happening perfectly.
The problem with this lack of plan
Because of the nature of our RTW trip, I have changed quite a bit since our visit to Europe. Back then I would get nervous and anxious with a lack of a plan. Add to it that I was carrying around an expensive ring without a clue as to when and where I was going to pop the question, and I was a wreck.
This was not lost on Megan. She realized something was up. Even though she assumed I was going to propose at some point in the next three weeks, she wasn’t positive, and my surly demeanor had her questioning what was up.
Since then she told me that she was nervous that I didn’t want to be with her anymore (a laughable assumption, but one that she was feeling nonetheless). Here we were, on our dream trip, and I was in a constant bad mood those first few days.
First stop-Dublin
Our first stop was Dublin, and we obviously had to go out on the town that first night because we all know the Irish love their beer, and we both love partaking in a night of beer drinking as well. We created our own little pub crawl, winding our way out of the city center and into traditional Irish taverns with the locals.
I was nervous, so I drank. At times I had a Guinness in one hand and a glass of Jamieson on the rocks in the other (hey, don’t judge, I was just embracing the culture). The drunker I got, the more nervous I became. Every time I would go to the bathroom, I’d take the ring out of my pocket to make sure it was still there (we were staying in a hostel, so I didn’t want to leave it there).
I made it through that first day, but it wasn’t pretty. As I woke up in a foggy haze that next morning, I knew I would just have to propose soon. There would be no waiting for 2.5 weeks until we arrived in Cinque Terra, Italy (a place I considered dropping to a knee before we left). There was simply no possibility I would last that long.
On day 2 the plan was to rent a car and drive across Ireland to Doolin and the Cliffs of Mohr. I was super excited to see this beautiful site, and I thought maybe I could do it there. Thoughts were swirling in my head, and the nerves became even greater as I thought this could be the day.
A wrench in the plans
As the plan in my head started to come together, Megan had the idea to head to Galway first instead of Doolin. We had met some people the previous night, and many suggested Galway as a great place to visit.
I reluctantly accepted this proposal as I didn’t want her to suspect anything. So we drove across Ireland, on the wrong side of the road, with massive hangovers. That alone was nerve-wracking. Add to it that my plan was going to have to wait at least another day, and I was a wreck yet again. We did not have fun in Galway. I was hungover, I was nervous, I was anxious. We didn’t do much when we actually arrived in Galway.
After a tame night of fish and chips, we were back in our little B&B and went to bed early. We weren’t feeling Galway, mainly because I was a mess and Megan was starting to question the entire trip. So we left and drove to Doolin.
Then it all came together
Sometimes, there is someone up above looking out for you. I am not a religious man, but I do believe in fate, karma, and things happening for a reason. We were meant to go to Galway that day. If we hadn’t, we would have taken a different route to Doolin. I felt a bit better that third day as we left Galway on a nice, sunny day, driving through the gorgeous Irish countryside.
I became excited, nervous too, but more excited that this could be the day. We drove along, chatting and enjoying ourselves. My demeanor was much more laid back, and I was starting to feel comfortable and get in my travel groove.
We were cruising around the narrow, windy roads when all of a sudden, after a turn, something appeared seemingly out of nowhere.
A stroke of luck
In the middle of nowhere, a beautiful little castle appeared. Not much was around, so we decided to stop and check it out. As we were getting out of the car, I instinctively grabbed my coat (with the ring in it), and we walked towards the Dungaire Castle.
We entered and found out it cost 5 Euro to hike up the stairs to the top. “Why not?” we thought. So we hiked up the old, winding staircase, stopping here and there to check out various rooms, to the top of the castle. We reached the top, came out and admired the beautiful views of the luscious green Irish countryside. We wandered a bit on the top of this castle, realizing we were all alone.
Then it hit me. Here we were, alone, on the top of a castle in the middle of the Irish countryside. There was no way I could have planned it any better. So I grabbed Megan’s hand, dropped to a knee, expressed my love, took out the ring, and asked her to marry me.
I remember the entire experience like it was yesterday. A genius stroke of luck allowed me to propose on the top of a freaking castle in the middle of Ireland. All because I threw caution to the wind for one of the first times in my life and didn’t make a plan. I let spontaneity take over, and thank God I did.
Now here we are, nearly 6 years later, after having created so many more awesome memories together. So many of our memories revolve around travel, my second true love next to my wife. And I wonder if it would have been any different had the proposal gone another way? If I had planned it all out, would it in some way have changed? There’s no way to know of course, but it’s an interesting thing to think about.
Fate threw me a few curveballs those first few days, but it did so for a reason. The day I proposed to my wife is one of the most vivid, memorable days of my life, and I can’t wait to revisit the Dugaire Castle someday, perhaps with our kids, to relive the entire experience.
Happy Valentine’s Day everyone! If you have a romantic story to tell that revolves around travel, I’d love to hear about it in the comments below!












