Mike’s Engagement Story

Last time we ran our 14 Days of Valentine’s Day Blog Series, Jenny shared her version of how I proposed.

We were married on October 25, 2008 and it’s been 6 amazing years of marriage!

Although I proposed in September 2007, I remember the details like it happened last week:

My engagement story with Jenny is a fun one – it definitely was me at my most romantic. I tried to pull out all the stops, and in the end, things turned out great. Jenny and I had been dating for a few years at this point and I could tell that she was interested in the ‘next step.’

First, I quit my job at Guitar Center and started working at Helzberg Diamonds. The pay was the same, but I figured that if I got a good employee discount on an engagement ring, it’d be good. As long as the pay was the same, I might as well spend less on something I was planning to buy anyway. The job was in the mall, which really sucked, but after a few months of working there I picked out the ring that I’d seen her look at every time she came in to visit me.

When Jenny was in high school, she wanted to go to college in Boston, and had never been there, so I thought that a romantic weekend would be nice. I booked a trip to Boston for the weekend – hotel, rental car, flight, the whole nine. I put the whole thing on my credit card, didn’t give it a second thought. This was all to be a surprise to Jenny, she didn’t know that any of this would be happening. The morning that I picked up the engagement ring was the morning that my employee discount kicked in, and a few hours later, our flight was to take off from HIA. So I was planning this whole thing around the employee discount kicking in, haha. This was in early September.

So I called Jenny’s boss and got her shifts covered, without her knowing. And I had Gretchen call and tell Jenny that class was cancelled, and I asked her if she wanted to come with me to the mall to pick up my paycheck. I was actually there to pick up the ring, and then after that, I blindfolded her, and drove her to HIA. I’d already packed her bags, and when I took the blindfold off, she was looking at an Airport Shuttle, and I was telling her to get on. She was astonished, confused, and surprised – to say the least! I was petrified that the ring would set off the metal detector, and it was the first real plane flight I’d ever taken in my life so I had no idea. But I was really scared that Jenny would get the hint that something big was happening, or that the surprise would be spoiled in some way. I had the ring in a little velvet bag in my pocket. The whole way there, I kept touching that pocket to make sure that it was still there.

We got to Boston in one piece, got the car, and unpacked at the Hotel. Friday we just kind of putzed around Boston, checking out the sights, food, and taking in the culture. Saturday, we spent time walking around downtown Boston, Faneuil Hall, and other Boston landmarks.  We did one of those Duck tours, too – that was really fun. Kept touching my pocket, ring was still there.

I had two plans – Plan A, and Plan B. Plan A was the one I wanted to do, but I ended up needing to go with Plan B. Plan A was me popping the question on one of those swan boats in the park in Boston. So we get to the park, I had a backpack with a camera so someone else could take a picture of me doing it, that kind of thing. We get shuffled onto a boat with like, 15 little Chinese girls that don’t speak any English. So I couldn’t really ask them to take a picture. We’re puttering around the pond there in Boston, but it was really hot outside, I was wearing a sweaty Led Zeppelin shirt, there’s duck and goose poop floating around in the water, and it just didn’t feel right. I aborted and went with Plan B, which was to pop the question at the Skywalk at the top of the Prudential Building.


I had reservations at the Top of the Hub restaurant in the Prudential Building in downtown Boston. I nearly didn’t make the reservation because I didn’t have a GPS – just printouts of Mapquest directions. But we made it on time, and had one of the best meals of our life in the second to the top floor of this historic building in Boston. Near the end of dinner, the waiter asks me if I want tickets to the Skywalk, and gives them to me for free – but tells me to hurry because it’s about to close. So Jenny and I settle up, and we dash upstairs to the Skywalk – and it’s this completely open, floor-to-ceiling window space at the top of this huge building, dozens or stories up overlooking all of Boston at night. And we were the *only* ones there because it was about to close. It was perfection. I got down on one knee, waited for her to turn around and see me. She did turn around, gasped, and I popped the question.

Through tears, she said yes, enjoyed the moment, and then went out to get doughnuts at a pastry place in the Italian District.

The rest of the trip was a lot of phone calls to tell people, little restaurants here and there, and walking around Boston taking in the sights. I’ll never forget the wink the waiter gave me – he knew what I was doing. I’ve never been more excited for something in my entire life. I knew she was going to say yes, but I really wanted to go all out. The ring was expensive, the trip was expensive, but it was something I don’t regret looking back and to have that trip together was amazing. There was a lot of excitement before I popped the question – Boston is an exciting city, and we were stoked to be there, just as a dating couple – but after she said yes, being there took on a whole new meaning.

I’d love to go back there with her someday and relive portions of that trip. I made note of all the places we ate, and went. Maybe for our 10 year anniversary? Stay tuned. This is our tenth year as a couple, and it feels like our wedding was just yesterday. She’s made me the luckiest guy I can imagine. We’ve changed, but we’ve stayed the same, too. 🙂





*Wedding photos by KMPhotgraphy Studio



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