Caitlin and I were destined to meet. During Ben’s first week of work at Microstrategy (five years ago), Caitlin was the girl who on-boarded my confused fresh-outta-college then boyfriend/now husband. He came home from work to announce, “I met a girl who is friends with Spencer Booth!” This may seem like a very weird thing to celebrate but I think it was comforting to have found a familiar friend at a brand new job, let alone his first real job.

Fast forward a few years and our good friend Spencer is texting me from California saying that his proposal to Ali had been put off due to rain and now they were having dinner with their friends who just got engaged in Napa right before them! Little did I know, that couple was Caitlin and Matt! I had the incredible pleasure of snapping BOTH of their engagement sessions in two major cities during breath taking sunrises. Smallest. World. Ever.

Sometimes, I feel like I can’t do a couple’s story justice. In this case, Caitlin was kind enough to share their love story and it’s just darling! Reading all the details below make you fall in love with this couple: 

“Matt and I met while working together at a benefits consulting firm. When you first start, you’re assigned a peer mentor who basically was someone to go to for questions and/or guidance. Matt had already been with the company for about a year and he was assigned as my mentor. The mentorship also consisted of monthly mentor/mentee lunches. I remember going on my first lunch “date” with Matt and feeling extremely nervous as if I was going on a real date with him. Over the course of the next couple of months, during each mentor/mentee lunch we spoke less and less about work and more about ourselves. I was talking to him about how I was going home to upstate NY for the weekend and was bragging about all the great Italian food I was going to be eating and all the homemade food I had in my freezer. It was then that Matt invited himself over to my apartment for me to cook him dinner and he persuaded me by saying he’d bring the wine. Matt was in CA that following week for work and brought back a bottle of wine from Chimney Rock Winery in Napa Valley. He brought the wine so I had to fulfil my end of the deal so I cooked him chicken parmigiana and we drank some delicious wine from Napa for our first date.


A year later, in October, Matt was back in CA for work. I had never been to Napa Valley before so we decided after Matt’s meetings were over that I’d meet him out in CA for the weekend and we’d go to Napa. We rented a sweet little house for the weekend and planned on going to a couple different wineries for tastings. Chimney Rock was the first winery on our list since Matt had brought us a bottle back from there for our first date. We started off by doing a tour of the winery, seeing the vines, their barrel room, learned about how the wine was made etc. Then we went inside to do our tasting. Everyone was doing their tastings at the counter when you first walk in but we went to a private room in the back. As soon as we walked in the room I knew that Matt was going to propose. The room was so beautifully set up with flowers on the table, five wine glasses, cheese/crackers and a menu that said “Welcome Vallario party.” I was nervously sitting there and Matt could tell that I was catching on to what was about to happen so he tried throwing me off. He told me that he knew this weekend would have been that much more special if there was something else that was going to happen basically trying to tell me that he wasn’t going to propose. Once he said this I calmed down and pretty much called him out saying I thought he was about to propose! At this point, he couldn’t hide it any longer and told me how he had been lying to me and that he had something for me, got down on one knee and asked me to marry him. We continued the celebrations over the weekend drinking some of the best wine that we’ve ever had!”