A Surprise (Proposal) Trip Across The World… We Leave Tomorrow

One day I happened upon a travel website that was offering a contest where the grand prize was a trip anywhere in the world, but the catch was, the winner must leave within 24hrs.

My long time girlfriend Erin, and I loved to daydream about topics like this. I asked her where she would go, and she emphatically declared Italy! I knew we probably had no realistic chance of winning this contest, but that wasn’t going to stop me from making my future wife’s dream come true. From that moment on, my plan to take Erin on a surprise trip to her dream location began to take shape.

I visited with Erin’s little sister Stephanie, who was my partner in crime in planning this little engagement. When I explained to her my intentions and what I was planning to do, she was so overjoyed with excitement for us. I remember telling her, “Hold on, there are still a few obstacles to get thru, and any one of them could stop this plan in its tracks.”

Over the next few months we began to chip away at the details. I casually asked Erin, “Do you even have a passport”? To which she replied, “yes, but I don’t remember if it’s expired.” My heart sank because I knew if her passport had lapsed that would be a plan stopping obstacle. So task one, find Erin’s passport. At that point in time, we both lived at separate condos in Dallas, Texas. We both had each other’s house keys, so one day when I knew she was busy, Stephanie and I went on a secret mission to somehow find her passport. It was like looking for a needle in a haystack, but after about an hour, we found it! Step one, complete!

One of the biggest issues when planning a surprise trip is having to make arrangements for yourself and someone else without the knowing. Even trivial things to plan for yourself, tend to me a lot more difficult when you are planning this for someone else. Case in point, asking for time off from work.

Erin works at a large accounting firm in Dallas, KPMG. Which has a busy season where no one can take vacation. I knew when this time was, but they frequently have intermediate deadlines that I never seemed to know about. So I couldn’t leave it to chance, I had to ask. The problem is, I had not, at that point, met her manager. So, one workday I called, 1-800-KPMG and after about a half hour on the phone, got the phone number I needed. I call the number and got her managers secretary, her manager was out of the country. After pouring my heart out to her secretary and laying my entire plan out, I finally got her manager, Rachel’s email address. Then we began emailing back and forth. Eventually Rachel agreed to give her time off without her knowing, and we agreed on a date.

After jumping over a few other hurdles, asking the parents’ permission, buying tickets, and about twenty other items, finally the days were fast approaching. I had initially decided that this secret would be on a “need to know” basis. Well by the time the reveal day arrived, everyone knew and was in on the secret, and bursting with excitement for me to tell her.

Wednesday October 23rd I told Erin over dinner at Macaroni Grill, that within 24hrs we would be on a plane bound for Rome, Italy. She was giddy with anticipation and excitement, scrambling around packing in the next few hours. We both couldn’t sleep that night, and the next day we started our journey. Being an amateur photographer, I wanted to make sure to capture our journey.

We had more fun than you could ever imagine in Rome, Italy. We shared candle lit dinners on the cobble stone street cafe’s, and regularly frequented the local gelateria to grab some Gelato. Also, we never missed a chance to sneak back into back ally’s for a little make-out session. The second day of our trip, I decided this was going to be engagement day. I planned a trip thru the town ending at the Spanish Steps. We shared a few moments sitting on the steps when I pulled out a ring from my camera bag. To her thrill and astonishment, I got down on one knee and made the best decision I’ll ever make.

On the ride home the customs official asked me if we were returning from business or pleasure? I of course said, pleasure, but I remember thinking that it felt more like a business. I had serious business to tend to, and it was a success.

Every couple should have a love story, and this story has become a big chapter of ours. People have asked me how in my early thirties, I was able to afford such a lavish trip when I could have spent the money on so many other, more practical things. I’ve always proclaimed that this wasn’t lavish, it was an investment. An investment in the woman I love, and the life that I wanted for myself. Investing in your own happiness and the happiness of your loved ones pays more dividends than any stock or real estate investment that you could make. Since the moment I met Erin, I’ve always wanted to find more ways to make her happy and see that beautiful smile. What can I say, I fell in love. I feel in love with her charm, her quiet (and sometimes not so quiet) elegance. She’s so much more than I ever could have imagined for myself. More than a pretty face, more than a beautiful spirit, more than a lover, and more than a friend. I greatly cherish all the days I’ve known her, and look forward with excitement and anticipation to all the days to come.

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