Brenna and Phillippson

Salem, Massachusetts



Photography | Jess Sinatra Photography | @jesssinatraphoto

Location | Salem Common

From the Photographer

Philippson and Brenna have been dating for 7 years before he finally decided to *pop the question* on the day before Thanksgiving right in front of Brenna’s fourth grade students! Along with two of her favorite past students to accompany him during our big moment. It was very appropriate for him to ask her in school as they went to the same high school together. Although he had a failed attempt at talking to her back in the day (or so he says… She recalls no such encounter) they reconnected a few years later when they began secretly dating. And here they are! Since they have been together for so long, their engagement has been moving pretty quickly.


Their winery wedding is set for 11/28/20.

Let’s start at the beginning. How did you two first meet?

Philippson and I attended the same high school, St. Clement in Medford, MA. I am older and was in a grade above him but had a lot of classes with his sister, Faranella. Our school was very small so everyone knew everyone but Philippson and I hadn’t really hung out until years later. Contrary to what Philippson would tell you, I absolutely did not turn down his advances back in the day – he loves to tell people he tried to say hello and I gave him a “pssshh” as I scurried off to class. Over the years, I had befriended his sister and often hung out with their group of friends when I would come home from college on the weekends. Always the life of the party, Philippson was always very easy to notice and though back then, no one would have imagined that two total opposite people would “work”, some flirtation began. Fast forward to a few years later, we both realized we had a bit of a crush on each other, and, as they say, the rest is history.


What makes your relationship special? Tell us some things that you both value in your time together. What makes your relationship unique?

Philippson and I have developed a true friendship over the years. Of course we have our disagreements (as all couples do) but most of the time, we’re just laughing and enjoying each others’ company. No matter the setting, we always find ways to laugh – often times at the others’ expense but laughing just the same. We are best friends and love to just be with each other.


How did you know your partner was the one? When did you first know this in your relationship?

I realized that Philippson was the one when I saw myself being my true self around him. He accepts me for exactly who I am and although we’ve been together for almost 8 years and have been through so much within that timeframe, he has always loved me for me. We both push each other to just be better humans but all the while accepting each other for our personality quirks, temperamental moods (at times), and sometimes odd sense of humor. We are both very different but it’s because of these differences that we just work together. We are both the biggest fan of each other.


Give us all the details about the proposal. How and where did it happen? Was it a surprise? What was the planning process?

We got engaged on November 27, 2019. It was the day before Thanksgiving, also known as my favorite school day of the year, and I was chatting with my fourth grade students about what we would be doing to assist the first grade teachers in their annual Harvest Breakfast event. I was kneeling down on the floor, fluffing up some decorations for the event, and my friend Erika, one of the first grade teachers, came in to create a diversion. All of a sudden, I see two of my former students, Belen and Pampam, walk in with flowers. Philippson followed them in I knew right away what was about to happen. My students gasped, Philippson gave his speech (the improvised version, not the one he had practiced), and he got down on his knee. I don’t think I answered right away but eventually an “absolutely!” came out of my mouth. Philippson joined us for the Harvest Breakfast and I finished out the school day on cloud nine.I later found out that this had been in the works for a few weeks. My grandmother, parents, Erika, and former students were all involved in his planning process. My fourth graders remember that day as a highlight of their school year. It is a day I will never forget.


We’re all about the bling… Tell us all about that ring!

Even all these months later, I still catch myself staring at my ring. When the lighting is just right and the sparkle hits – I know I’m not alone in this! Despite the style and sparkle-factor, the most special thing about my ring is that the center diamond is from my grandmother’s wedding ring. My grandmother, or Nana as we call her, offered her diamond to him knowing how special it would be for me. Nana is the most important person to so many of us and knowing that I will forever be able to carry that part of her with me is so special. One football Sunday, Philippson went over to let her know that he was ready to propose and, of course, she was over the moon. The ring is rose gold, halo style, absolutely perfect… but the most important thing is that it has that piece of my grandmother.


What are you most excited about when it comes to your wedding planning?

Wedding planning had been very easy and relatively stress-free leading up to the past few months. Philippson and I visited one venue, LaBelle Winery in Amherst, NH, and immediately fell in love. It had rustic and industrial elements that we were both looking for – the wine aspect was certainly a plus as well. Next was finding our photography/videography team and Jess Sinatra was suggested to me by a college classmate via a Facebook inquiry. Once we met Jess and her husband Evan, we knew it would be a great match as they made us feel very comfortable. All of the vendors we ended up choosing are all fantastic and we look forward to working with them for our wedding day. Though the current world events slowed down our process a bit, we were lucky enough to have locked down our main vendors before everything shut down. The next big thing we’re looking forward to is deciding on the menu and bar options for our reception… and most definitely going for the donut wall option that the venue provides!