Jacquelyn and James

How We Met

Four and a half years ago Jimmy and I met at a Southie bar, Shenanigans, on the Friday of the worst week of my life. On that Wednesday my entire purse had been stolen while on a blind date leaving me to piece back together my life. On Thursday, my mother went into the hospital for her first time with complications from the Ovarian cancer she was fighting. To make matters worse, I somehow managed to get a speeding ticket on each of those days. I was introduced to Jimmy by a mutual friend and I immediately decided I would set him up with a girlfriend of mine who happened to LOVE redheads… tan & Italian was certainly more my type. After chatting for a while, I introduced him to my friend and was surprised when kept talking to me instead of her. I began questioning him about why he was not pursuing her and finally he said “she’s just not my type!” Blonde and beautiful– I had no idea what could possibly be ‘not his type’ about her so I demanded, “WELL WHAT IS YOUR TYPE THEN!?” and he responded, “YOU.” The rest is history.

How He Asked

I have to preface this with the fact that I am a CRAZY horse girl. I am a competitive equestrian and many of my weekends are spent traveling the east coast to competitions with my beloved horse, Sophie. In fact, in the video, the first words out of my mouth are “Where is Sophie!!??” Jimmy is well aware of my obsession as well as my love of meaningful places.

Proposal Ideas Karen Stives Equestrian Center at Dana Hall School in Wellesley, MA

Thus, he decided to propose at the barn on “Mac Patio” which my father donated in memory of my previous horse who passed away in 2012. The barn is located on my high school campus, Dana Hall in Wellesley, MA….bonus points for being extra meaningful!

Where to Propose in Karen Stives Equestrian Center at Dana Hall School in Wellesley, MA

He decorated the patio with rose petals and balloons spelling out Will You Marry Me (good thing because he was almost too choked up to talk!!) and enlisted all of the “barn girls” to help make the proposal a surprise and extra special. I always told him, ‘I better look good when you propose!!’ so he had one of my friends, who is an instructor at Dana Hall, convince me that I was being interview by the news show, Chronicle. I somehow believed them… got my hair done, slipped on a nice dress and sat in 2 hours of Friday night traffic to have my “big screen debut.”

Wedding Proposal Ideas in Karen Stives Equestrian Center at Dana Hall School in Wellesley, MA

When I walked up, Jimmy was waiting for me on Mac Patio and wasted no time getting down on one knee and asking me to marry him. I took one look at the guy who somehow pulled all of this off and the most beautiful ring I had ever seen and obviously said YES!

Marriage Proposal Ideas in Karen Stives Equestrian Center at Dana Hall School in Wellesley, MA

That’s when I noticed he had hired a college friend, Lindsay Connors, to take photos of the proposal. I had hinted at him months ago that I would love Lindsay Connors Photography there to capture the moment. He is good!! If I wasn’t thrilled enough, he told me that he and my best friend, Jackie, (my future MOH) organized an after party at the Sail Loft, owned by another one of my friend’s family. All of my friends and family were there to celebrate! WHAT an amazing night!!

Our Video

Posted by Jacquie Maggiore on Monday, May 22, 2017

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