Engagement Shoots

Sunny Spring Engagement in Chicago’s Loop – Caitlin & Chris

Caitlin and Chris met on Bumble – Caitlin was drawn to Chris’s adventurous pictures of him and some friends hiking in Whitefish, Montana; and Chris liked Caitlin’s caption quoting Will Ferrell in the movie Elf: “I just like to smile, smiling’s my favourite”. After chatting with each other about their interests and families, they looked forward to meeting up in person on April 4, 2016, but given it was a typical chilly Chicago spring, Caitlin picked a location about a 2-minute walk from her home. Luckily, the sparks from the evening, talking about lots of shared values and hobbies, and Chris’s fantastic sense of humour inspired more interest on both sides and the romance kicked off. Their first summer together was filled with fun memories with family, friends, and also Chris’s first sailboat rental – and the rest is history!

As a couple they love to plan adventures together with their families and friends, which has led to kayaking in Mexico, wine tasting in Napa, camping in Indiana, BBQ in Austin, live jazz in New Orleans, bourbon-trailing in Louisville, cheering on the Bengals from the sidelines in Cincinnati, snorkeling in Key West, and so much more!! All of which sometimes makes for a busy schedule! But they also love making time to see their families as often as possible, treasuring the routine with Chris’s tight-knit Italian family of a wonderful Sunday-lunch tradition (generous portions over 5+ courses – with many of the delicious ingredients sourced from his parents’ garden – as well as some amazing family wine which the Fiordirosa’s have been making in their backyard for over 65 years!). With Caitlin’s family also based in the Midwest, they are lucky enough to see Caitlin’s parents and brothers about as often as the Fiordirosas, for exploring in Chicago as well as Cincinnati and Key West!

When it came to the proposal, Chris planned an incredible surprise! He set up a date night at a new fun steakhouse, Steak 48, where he said he’d met an amazing waiter a few times for work dinners and they had really hit it off. They spent a beautiful day together doing some of their favourite things – a delicious, big breakfast; biking along the Lakeshore; lunch on an outdoor patio with friends; etc. Then they headed downtown in their date-night-finest to a great rooftop cocktail bar called Drumbar, in which Chris made sure to keep a good distance from Caitlin to avoid any chance of the ring box in his jacket pocket giving him away! After settling in at Steak 48 with a cocktail, Chris had David bring out special menus that Chris had made ahead of time that said “Chris & Caitlin Reserve Tasting Menu” at the top, with a special surprise message at the bottom – “Ti Amo, Vuoi Sposarmi”, which means “I love you, will you marry me” in Italian. Caitlin had been trying to learn some Italian given Chris’s family is Italian, and picked up enough of what the phrase meant to (finally) have an inkling that this was far from a typical fun date night! Chris had a beautiful speech prepared to lead up to the proposal and had a confidante at Steak 48 strategically placed nearby to take discreet pictures of the whole wonderful moment. After a joyous acceptance, their waiter David popped a bottle of their favourite champagne to celebrate, and they enjoyed one of the most delicious meals they have had together, as they shared the good news with friends and family, and basked in the glow of their excitement.

Chris and Caitlin never talked about specific ring styles together in any of their conversations about the future, but she trusted him completely, partially because he generously describes her style as “like a 1967 Chevrolet Corvette Stingray – classic”. “He got me what I think is the best ring in the world! It’s a beautiful, very sparkly solitaire with a white gold band. I feel blessed to have a guy who both knows me so well and is so generous of spirit to get me the perfect ring for me.”
Chris says, “it is true that Caitlin and I never talked about rings together. While we did talk about our future together I wanted as many elements of the proposal to be a complete surprise for Caitlin. Luckily Caitlin has two amazing friends (Hi Tiz, Hi Molly) who gently guided me in the right direction. Without them, I would have been a bit lost at the jeweller as he started telling me about cuts, colours, and clarity. Once I knew what I was looking for I went straight to a jeweller who was highly recommended to me by a close friend and the rest was history.”

Thank you to Elizabeth Greve Photography for sharing these images with us.

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  1. Elizabeth Greve Photography

    July 27th, 2018 at 1:48 pm

    Thank you for featuring these two! We had such a blast running around the city!

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