Madelaine and Johannes

How We Met

Jay and I first met through a dating app (a modern love story). Both of us weren’t expecting to find the person we would want to marry, but the universe always has plans of its own. Back then if you had told me that I would meet “the one” through a dating app I would have refused to believe you! After about four weeks into casual dating, Jay thought it would be best to have a talk about “not wanting anything serious” and shared that he wasn’t “looking for a relationship”. He later disclosed to me that even back then he knew he was in trouble and was falling hard. I, of course, played it cool agreeing to everything he was saying. This was the first time in a while I had felt excited about dating someone but wanted to play it safe (we both had been burned before). With that conversation behind us, nothing really changed, and if anything, our relationship only grew. It got to the point where the pressure to ”define the relationship” started to set in, which freaked Jay out so much so that he went MIA for three days!

Where to Propose in Boston, MA

After the three days, I finally received a text from Jay asking to meet up for brunch. Assuming the worst, I figured that this meant he was ready to end things but wanted to do it in person. However, when I showed up, I was surprised to find Jay sitting there with a HUGE bouquet of flowers. It was then he shared with me that there was no denying it anymore and that he wanted something more serious. Of course, I couldn’t make it that easy on him… he did ghost me for three days! I told him that although I appreciated the gesture, I needed to take some time to decide if this was something I wanted too.

Madelaine's Proposal in Boston, MA

I let him sweat it out for a week or so and then just a few days before Valentine’s Day I gave him a chocolate rose (our guilty pleasure was watching The Bachelor) and shared that I also wanted us to take the next step. He surprised me with a romantic getaway for Valentine’s Day (from the very beginning of our relationship he was always a planner!). From there the relationship took off quickly, everything just felt right. Jay is originally from Austria so before I knew it we were traveling across the country to vacation with his family, covering all the serious questions/topics, introducing him to my family, and sharing our hopes for the future!

Marriage Proposal Ideas in Boston, MA

Proposal Ideas Boston, MA

How They Asked

His version: 1.5 years into my relationship with Lainey I firmly knew she was the one for me. I started following a list of wedding websites on Instagram but struggled to find a setting that would match what I was looking for. Well-manicured fingernails and good photos, I kept reminding myself. Lainey’s only two wishes she had communicated to me – not exactly a whole lot to go with. After months of procrastinating, I finally landed on an idea that excited me – a private sunset cruise around Boston’s harbor islands. When I found a charter company who offered a 50-foot yacht for rent, I finally thought “this is it”. From that point forward, it felt like planning a mini wedding to me, reaching out to vendors for a boat, catering, photography, flowers, and table settings. Details matter to me – this occasion was no exception – I wanted it to be “perfect”.

Madelaine and Johannes's Engagement in Boston, MA

I finally landed on a Sunday and started praying that the weather would hold. The big day inched closer and closer, and my nervousness reached new highs. It did not help that said Sunday turned out to be the hottest day in the year – triple digits! I started to sweat, not just because it was boiling temperatures outside. On the big day, Lainey and I had a rather lazy start into our day. I casually mentioned around noon that I had a small surprise for her in the evening, nothing big, and it won’t take long.

Wedding Proposal Ideas in Boston, MA

In the Uber on the way to the harbor, my heart started racing, as I kept thinking about all the possible ways this experience could go wrong, might not meet her hopes & dreams. All those picture-perfect Instagram engagements came back to mind – of course, I had to pick this weather! … We arrived at the harbor 2 hours before sunset. Lainey had seen through my unsuccessful attempts to hide my anxiety and started wondering what the surprise was. When we arrived at the boat, I was delighted to see that we had a very nice crew with us and that there was a cooling breeze out on the water.

We set the course out to the harbor islands while cuddling up on deck and enjoying the Boston skyline – the place where it all began. After a few bites of tasty appetizers, the crew called me over and gave me a subtle hint – the light is perfect, it’s “go time!”. My hands started shaking as I pushed the ring down my pocket and walked over to Lainey to ask her to dance. My original plan was to play a special Ed Sheeran song for her, but my anxiety was too high. I started recalling a few of my favorite memories with Lainey and finally went down on one knee. The rest is a little blurry – but I remember “YES” and that I did manage to slide the ring on her finger. A few tears later she was officially my fiancée …

Her version: The morning of the proposal Jay had shared with me that he wanted to do a date night that night, which wasn’t out of the normal as we typically try to have date nights to make sure we spend time focusing on us. Throughout the day I kept asking him what he would like to do and making suggestions here and there. At first, he played along and then eventually shared that he had an idea but wanted it to be a surprise. Again, this wasn’t unusual… from the very beginning of our relationship Jay was always a planner for our dates and loved to sneak in little surprises. I remember for our first date he sent me a list of 14 different options, all of which were very thoughtful especially for a first date! Jay shared with me that we would be doing an “outdoor activity”, which I immediately gave him a hard time about saying “only you would plan an outdoor activity on the hottest day of the year (it was over 100 degrees that day)!

However, I played along and got ready then off we went. When we hopped into the Uber our driver immediately asked where we were going, which I had no answer to. Jay tried to dodge it but eventually shared that we would be going down to the harbor to walk around (one of his favorite spots in the city). When we arrived I asked Jay where we were going and he simply said “I don’t know” and that moment Amanda (who helped Jay with all the planning) came up and greeted us and explained that our yacht was ready! I was shocked! Jay shared that he thought it would be fun for us to take a sunset cruise together.

At first, I was a little suspicious, but he loves planning these types of surprises and I also thought he would be the type of person to plan something extravagant not proposal then propose the next day in bed! Cue the photographer, Lena! She showed up and introduced herself and explained that she came with the boat package to get some nice shots of us with the sunset. Now that everyone was aboard, we set sail to cruise around the Boston Harbor and out to the islands. Jay and I were enjoying the breeze and sights of Boston Harbor.

As the sun was beginning to set Jay asked me if I would like to dance, which I never pass up the opportunity to do! As we started to dance Jay began to give his speech (which at some point I think I blacked out from excitement) then before I knew it he was kneeling down asking me to marry him! I immediately said YES, and our crew on the boat started cheering. Lena quickly came over to us and was excited to share that she didn’t come with the boat, but that she was a wedding photographer.

After that, we popped some champagne, had an impromptu photo-shoot, and finished our cruise all while watching the most magnificent sunset. I don’t think I stopped smiling for even a second! Now that the big secret was over Jay shared to me how everything was planned all the way down to the littlest details; the music list he made to play throughout the cruise (although he was so nervous when he proposed he forgot to play the song he picked out for that moment), he picked out the flower arrangement, the table cloth which was my favorite color, and even the menu which was inspired from my favorite restaurant! Now each morning I get to wake up and call him my fiancé!

Special Thanks

Lena Mirisola
 | Photographer
Amanda Gallagher
 | Planning
Johnny Burke
 | Food