Hollis and Roderick | "Firsts” Themed Proposal

Photograph by Rebecca Yale Portraits.How We Met: Our first date was at a wine cellar in NYC. I was 5 minutes late, but she was patient enough to wait. Our date lasted over 5 hours just talking and having fun. On our 2nd date we went to “Cafe Wha” an underground venue with a live band, playing old school R&B. I couldn’t resist myself and we eventually shared our first kiss.

How He Asked: Hollis is a hopeless romantic but also very practical and had even commented to me that she would be happy if I proposed on the couch at home while relaxing. But I wanted something more personal for her.

One thing I definitely wanted to do was create a book for my future (not yet conceived) son and incorporate that into the proposal. The story would explain what love truly feels like and what that woman should mean to you. I contacted Proposal Planners, The Heart Bandits to help me come up with a way to incorporate the book and make Hollis really special.

Because our first date was at a wine cellar, I rented out a wine cellar for my proposal. I had this whole ruse planned out where Hollis thought we were there at the restaurant meeting some Venture Capitalists. The waiter approached us 5 minutes after sitting down to tell us the Venture Capitalists couldn’t make it and as an apology they wanted us taken down to the wine cellar to choose a wine. When we went down to the cellar, Hollis was blown away by my “Firsts” themed proposal. There was a sign out in front with an arrow pointing to the cellar that said “First date”. Inside the room was a gorgeous tablescape full of candles, bright colored flowers, and picture frames labeled with our “firsts” over the years. After we reminisced on all of the memories, I sat her down and presented the book to her and proposed at the end of it. She absolutely loved it!

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Photographer: Rebecca Yale Portraits // Proposal Planner: The Heart Bandits