This Couple Shocked Their Loved Ones With a Surprise Wedding

how we met

My husband and I met a year and a half ago on Bumble in Boston. He had just moved to Boston from Connecticut and I was fairly recently single. He left sleepy Connecticut with dreams of tech startups and a single summer. I was enjoying my single life with five of my best friends, who were also single.

We both swiped right! During the short days of a chilly Boston winter, Matthew and I were both swiping left and right on Bumble on different sides of the city. My default picture was a whimsical one of me in an oversized chair at the Museum of Science, a photograph he says drew him in and is still one of his favorites. While I thought he was handsome, Matthew’s “About Me” section intrigued me most and gave me the conversation starter I needed, as Bumble is the dating app where women need to send the first message. After chatting for a few weeks online, we had our first date on January 28th, 2016. We met at a local Boston bar called BeeHive, a location we now consider quite funny, having met on Bumble. Matthew arrived first and snatched two stools at the bar. After I arrived and we exchanged the standard greetings, we soon found ourselves lost in conversation and blinded by sparks.

He ordered a Dirty Martini, one of his favorite cocktails. I made a face, not being an olive fan myself, to which he asked if I had ever tried one. Two dirty martini’s each later, I received a text message from a friend grilling me about how the date was going and saying she was only a couple of blocks away with her newish boyfriend. Matthew poked fun at my texting but then actually suggested we go meet them, which is how my best friend and her future husband ended up on my first date with my now husband!

Matthew took me on his annual trip to Martha’s Vineyard that summer, during what was supposed to be his “Single Boston Summer.” Not planning for this serious of a relationship myself, the trip for me was sandwiched between two preplanned girls only weekends. At this point however, it was safe to say that neither of us were, in any way, single any longer. He introduced me to his best friend Nicole and her husband Mike that week, took me around the island he loves, shared his favorite bars and restaurants, showed me how he burns almost immediately upon exposure to the sun, and took me to watch the sunset down by the ocean. Despite our newish and unexpected “taken” relationship statuses, we both had one of the best summer vacations in memory.

how we planned it

The idea of a surprise wedding came up in conversation on a trip to Martha’s Vineyard in the Fall. We were having a conversation about weddings and marriage, and I brought up that I thought a surprise wedding would be fun, an idea that I had always kept hidden away for obvious reasons, but also because I had never dated anyone I thought would be interested in such an out of the ordinary thing.

It turned out Matthew not only loved the idea but ran with it! He was actually the one to bring up getting married during a “surprise” 30th birthday as a way to really trick everyone. At the time, this was all hypothetical. However, my 30th birthday did happen to be approaching. As the months slipped by, Matthew or I would bring up the idea once in a while, jokingly at first, and then more serious. By February of 2017, when Matthew brought it up again in conversation, I said that if he was serious about it, he needed to let me know because we had some planning to do. His response? “If you’re serious, so am I.” And that’s how the planning began.

So, despite not being engaged, we started to have a serious conversation about planning this wedding. There were a few things that I definitely wanted despite having a nontraditional wedding; a proposal, high quality pictures, an open bar, and dancing. Knowing the basics, we crunched the numbers and started putting everything in motion. We went to a few jewelry stores in Boston and looked for rings. I ended up picking out a center stone, a color changing sapphire and Matthew designed the rest of the ring with the jeweler. Check.

Matthew’s brother Andrew and sister-in-law Emily had recently gotten married and they had a fabulous videographer, Shane Films. Given the surprise aspect and after talking about it, we both agreed that we wanted a video as well as the photographs. We contacted Shane and he was free June 24th. Check. Shane got us in touch with a photographer, Tim Mannle of TBM Photos, who was also available and showed us his stunning pictures. Check.

We knew we wanted to do the ceremony, weather permitting, near the Charles River Footbridge in our neighborhood in Cambridge because it’s a spot we love to walk by and is simply beautiful. To pick out a venue for appetizers and drinks afterward we went on our own two-person bar crawl around Cambridge and picked our favorite cocktail lounge. Check. Finally, I ordered a white dress on Rent the Runway and we started designing the invitations. It was all so fun and romantic to plan together.

how he asked

Saturday, June 24th we woke up to stormy skies and rain. The surprise wedding was supposed to be outside at the bridge and…. We literally had no plan B. We knew this was a risk and figured that if it did rain we’d just have to figure something out that day but it was definitely a little stressful looking at the weather that week. Matthew is actually a huge weather nerd and he hired a weather blogger that week to update us daily on Saturday’s forecast. The entire week the forecast was basically “it’s either going to be perfect weather or it’s going to storm.” Money well spent. Luckily by 2pm the storms moved on, the sun began to shine and the humidity dropped. We knew we were in for a treat.

The lies continued throughout the day. Matthew had told everyone that I thought we were going away for the weekend. Suspicion arose when questions about “how are you going to keep her busy the entire day.” Since the “surprise” was to kick off at 8pm. All fair questions. Matthew came up with the idea to tell all of my friends that he was taking me on a scavenger hunt of sorts. The scheme included 31 envelopes (make believe envelopes, of course) each with a year on it starting from 1987, the year I was born. Each card had a clue that was to lead us through the day.

Things became tense when my friends began texting me asking what was going on. Hair appointments, manicures, a nice lunch and shopping were all made up on the fly. They bought it. Again. And it actually worked out really well because they had no reason to be suspicious when I showed up for the “engagement” all done up with hair and makeup. We packed all our things up and headed to our hotel. We had to scrub our apartment free of any evidence of the true plan because Matthew’s family was staying there for the night. There were invitations to hide, wedding puzzle pieces, and other random red flags around.

After we checked into the Charles Hotel we grabbed lunch with Nicole, our officiant and quasi best man. The nerves kicked in for Matthew here – the anticipation of the day started to kick in. He was so nervous for two hours or so. Could we pull it off? Is anyone going to run into us? Did we forget anything? Are the photographers on time? So many questions with no answers.

Once we finished lunch it was GO time. We had to get a few more items. Balloons for the meeting location, a guest book, and of course a bottle of champagne for pre-celebration. We started getting ready around 3:30. Our makeup artist Marlo arrived and worked her magic. Marlo was a referral from our salon, Clementine Hair Studio in Somerville, we had no idea what to expect. She crushed it – see our video for her awesome work. My sister Tricia, her husband Will, Nicole, Nicole’s husband Mike, and Matthew’s friend Kimi were the only ones in the know. Without the traditional wedding party help, this crew stepped up to make our day more special than we could have imagined.

Getting ready together was so very special for us. We were able to share that time together knowing we were about to shock the heck out of everyone by getting married. You could feel the energy in the room. Our family and friends were pumped, the videographer and photographer were just as stoked too. They’ve done countless weddings but the concept we were about to pull off made it extra special for them. After we got ready we headed to an area in Cambridge, next to the Charles River, that overlooked the Boston skyline. Matthew and I picked the location out mainly because of the back drop. The city of Cambridge recently redid the walking path with new grass and trees. It was beautiful. The sun was in perfect position to light up the city as it started to set in the west. The engagement on John Weeks Bridge was the first surprise. Walking along the Charles River, headed to the bridge, I remember saying “I’m so nervous, I think I am going to pee my pants” to Matthew. He held my hand tight and pulled me close replying “we are almost there – deep breaths” (see in video).

The last few minutes were tense. A wedding would make us nervous alone but add in a double surprise – you could feel the excitement and anticipation in the air. Our family and friends were right where we planned on the other side of the bridge waiting for us. We sent Kimi and Nicole ahead of us to get everyone in position. Kimi helped with the balloons, the meeting point, and direction given in the invites. Nicole was there to help guide the crowd if need be. Nicole texted us as we were getting close to the bridge. “We are all at the footbridge. Everyone anticipates engagement… let’s do this!” We knew we had them. Hook. Line. Sinker. And then some! We walked up the bridge trying to look natural – the butterflies were out in full force.

We made it almost halfway up the bridge and it happened. The fake engagement. Matthew likes to call it the second engagement because it felt so real, so much love was in the air and so many loved ones were there for us, and they didn’t even know how important of an event it really was! Matthew got down on one knee – his voice broke overcome with emotion “Jennifer Michelle Gilpin – will you be my partner in life – will you marry me?” I tease him that I didn’t think he asked me to marry him the first time. This time he definitely did.

As our family and friends walked up the bridge we shared a moment of laughter and relief – part one completed. The amount of love felt in that moment is impossible to describe. Our family and friends all there for me and for my surprise engagement. They were so happy for me, so happy for us. They knew that we found each other and were so happy that they could be there to celebrate the moment. Matthew was mic-ed up at this point and several people questioned it, one being my friend, Theresa. Matthew told me afterwards she asked what that was for and he said “it’s part of the photo shoot I am on with Jenn, it’s all part of the scavenger hunt.” That was the last lie!

the wedding

The plan, thanks to Tim our photographer, was to get the crowd off the bridge back to the Cambridge side. It took time and a few “get off the damn bridge” moments to get everyone in place. With the cameras in place we knew what was to come but we didn’t know how to do it. We discussed a few ideas on how to drop the mic, as they say, but there was no rehearsal, no walk through, we had to make it up as it happened depending on the reaction the crowd.

As fate would have it, Kimi tied the balloons to a lamp post. Perfect. The wedding Gods were on our side. Matthew had the idea to walk over to the balloons untie them and let them go into the air. Did I mention I was wearing a black skirt over my white dress? Yup, the ultimate bait and switch. No one would question a medium blue pair of slacks and a vest but a white dress on me would totally give it away.

We walked to the lamp post – at this point I was losing my mind – so nervous. I grabbed the balloons and Matthew began to untie my black skirt. I let the balloons loose and almost as we planned it, people’s eyes followed them up and up and up and when they looked back I was all in white… and at this point people’s faces went blank.

They were shell shocked – no one really knew what the hell was going on. My mother figured it out with a little help from my sister but as we walked closer Matthew yelled to everyone “That wasn’t the surprise, we’re getting MARRIED!”

That was it – we did it. People were floored. Jaws dropped and tears began to fall again…

With our friends still confused, we went right into the ceremony. Nicole met us at the bank of the Charles River and with the sunset behind us we married. It was better than I could have ever imagined. It was a day about us. A day full of surprises. A day full of love. We did it the way we wanted to do it.

the video

the reception

After the wedding all our family and friends walked over to Park Restaurant for food, drink and celebration. Matthew wanted to stay behind for a few more pictures. It was getting dark now and the bridge was all lit up. I’ll admit it – I wanted to go see my friends now and was being a bit of a brat but my now “husband” asked me to stay for 10 minutes to take a few pictures. Begrudgingly I did and I am glad he made me stay. We captured one of my favorite pictures of the night.

We walked to park hand and hand to meet our family and friends. Back at park people were still in shock. It was a night of confusion, explanation, love, and laughs. My last request of the night was to dance. There’s a dance club called Hong Kong in Harvard square. It’s usually a spot for college age drunkards but we knew it wouldn’t be too busy with school out for the summer. We all walked over and danced the night away. It was a blast.

The Aftermath

You know when you throw a pebble in a pond? That’s exactly what happened. Over the next several days and weeks we were bombarded by phone calls and text messages. “Congratulations,” “You guys are crazy,” “What the hell?”

Later that week we attended my friend’s birthday party at Carrie Nation in Boston, the first time since Sunday we saw anyone. We were able to debrief everyone and hear their experiences. From the moment of surprise to the Monday after when back to work we had friends, family, and work colleagues losing their mind over what happened. We had the opportunity to listen to their experience of Monday morning asking about the engagement only to hear that everyone was duped – it was a wedding…then the video came out a few days later. Amazing.

When we first started planning I knew I wanted an awesome photography and I got one. We were so lucky to have decided to capture everything on video but even more so find someone to piece it all together in an Epic, and I mean epic, video. Friends who we haven’t spoken to since high school, people who we’ve haven’t even me, reached out to us with congratulations many of them saying they cried as they watch our story over and over again. Shane and Tim were able to capture the essence of our love and story so we could relive again and again. It was truly an amazing and loving experience.

special thanks

Photographer: TBM Photos
Videographer: Shane Films
Officiant: Nicole Dombrowski
Florals: Brattle Square Florist
Jennifer’s Dress: Rent the Runway, Nha Khanah
Hairpiece: Rent the Runway Bridal Accessories, Pearl Twist Large Comb
Earrings: Kay Jewelers
Purse: Rent the Runway, Inge Christopher
Makeup: Makeup by Marlo
Ring: Family Heirloom
Matthew’s Apparel: Macy’s Alfani
Shoes: Steve Madden
Belt: Ryan Seacrest
Bow tie: Etsy Wood Carved Boston Skyline Tie
Ceremony Location: Charles River, Cambridge, MA
Reception: Park Restaurant & Bar, Harvard Square
Rings: Custom engagement and wedding band