Two Stylish Gents, One Incredible Italian Engagement
December 2, 2016
Fall Weddings
"Stylish" doesn't even begin to describe the engagement session of Tom and Tim. In fact, these two gents took their impeccable sense of fashion and paired that with the backdrop of Tuscany for absurdly romantic photos captured by Rebecca Yale. Join us on their trek through Italy with lots more right over here.
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From Rebecca Yale Photography... My favorite thing about engagement sessions is they get to be a little slice of life so is there anything better than a destination engagement session which can perfectly capture the memories of an incredible trip exploring the Tuscan countryside? I spent a lovely Fall weekend photographing the incredibly sweet (and fashionable) Tom and Tim at Il Borro, a 1000-year-old castle estate, and medieval village in Tuscany owned by the Ferragamo family.

Tim, a former bronze medalist Olympic Ice Skater, was celebrating his master's degree from NYU and of course their recent engagement. Tom popped the question at the historic Chanler in Newport, RI, where the couple will say their I Do's next year. The trip was spent wine tasting, sightseeing in Cinque Terre, truffle hunting, shopping and eating way too much incredible Italian food. Minus a little rain in Cinque Terre we lucked out with a perfectly gorgeous Fall weekend, getting to enjoy the bright red leaves crawling up the wine caves and the perfect little breeze as we explored the medieval town.

The Proposal

From the Grooms... Planning an engagement proposal is very involved as there are many moving parts. For Tim and I, it started about 18 months before I actually proposed. In a non-traditional move, I mentioned to Tim that one day I could see us getting engaged. However, it would happen only after he went back to school to pursue a Masters in his field. With the proposal out there, I assumed it would be at least two to three years before we would potentially have serious conversation around being married; after all, at this time, marriage equality wasn't even passed in New York yet and it was well before the Supreme Court decision made same-sex legal across all 50 states. But, Tim applied and was accepted into NYU Stern's Masters program by that Fall 2015.

During the time that Tim was in school, I spent a great deal of time looking into unique options for a potential engagement. Ideas ranged from watches to cuff links, to bands, to an actual diamond, to just words. At the end, I worked with a jewelry designer in designing a unique diamond ring for Tim for our future engagement. This process took six months from start to finish. With the ring completed in late March 2016, I reached out to his parent's to schedule a weekend together in early April while Tim was preparing for a series of exams with his programs. I arrived at his parents' home in Arlington Heights, IL with a bottle of champagne and ring in box. His parents had a very strong idea of why I was there as their smiles were cheek to cheek upon walking in. Tim wasn't aware that I flew to be with his parents for the weekend specifically; I mentioned that I was in the area for work and figured I'd stop by and spend time with them while he focused on his school work.

I asked Tim's parents for their blessing to have the honor of asking Tim to marry me. His parents were beyond excited and we began celebrating from that point forward until that Sunday, which is when I headed back to New York to see Tim. Tim asked what exactly I was doing with his parents that weekend. I noted we were shopping for his graduation gift. So, upon returning home to New York on Sunday afternoon, Tim demanded that I share with him what I brought back for his graduation gift from his parents. The only thing I brought back was his ring.

Tim insisted on seeing the gift and went through all of my luggage. Fortunately, I had the ring in my pocket. I realized at this time that I was not safe in our home with the engagement ring - and with time, he was going to find it. So, we went for a long walk along the Hudson River. We ended up walking to where we first had cocktails together, Orient Express. We were the first guests of the day as they opened at 5:00pm. We ordered a cocktail and Tim inquired about his graduation gift from his parents. I started to laugh; I had no choice because of what I knew and he didn't. Also because I was pretty sure that my perfectly planned proposal was about to be replaced by an impromptu proposal. Tim looked at me, grinned and asked what was so funny. I turned to him, took his hand, went into my pocket to pull out "nothing" and ask for his hand in marriage. Tim looked at me and sternly said, "this is not funny. You have repeatedly asked bent down on your knee before and proposed, you have repeatedly asked him in public for my hand, and you're doing it again." To which I replied, you're right. Let me try one more time. So I went back in my pocket to search for the ring (mind you, I couldn't find it in my pocket the first time as it was stuck in the crevice of the pocket) and presented Tim with a ring and a request for his hand in marriage. Tim was in shock and couldn't believe it had actually happened. But it did. We toasted over another round of cocktails and made our way back to Perry Street to celebrate.

It wasn't the proposal that I had spent the past few months planning in advance. However, I wouldn't have changed it for the world as it brought us full circle from where we first fell love in one another to making our relationship "official" with a proposal.
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