They've known each other practically since birth. Her dad's brother married his mom's sister - don't worry they are NOT related haha! But they grew up together and had big crushes on each other when they became teenagers. At age 15 Lisa moved to Connecticut, and although they lost contact, their connected families made it so they were never disconnected. Bobby would ask about Lisa at family parties, always wondering what her life was like.

Still, they lived separate lives until just a few years ago.

The two met again as adults, and the innocent pure love they shared as children was immediately rekindled. They soon realized they had the mental, physical, and spiritual connection that so many dream of.  Bobby knew that one of Lisa's favorite places in the world is Times Square, and he knew his proposal had to be something unique and special to them as a couple. Eventually he came up with the idea of using a big screen in Times Square to ask for Lisa's hand in marriage.

He also invited a musician to help them celebrate by playing two of Lisa's favorite songs during the proposal - "Belle Notte" from Lady and the Tramp and "So This is Love" from Cinderella. Seems pretty good right? Well, it gets better! He also planned a dinner immediately following our session...at the Manhattan's only revolving rooftop restaurant! And after dinner, he took her to see Phantom of the Opera on Broadway!! Oh, and did I mention he also left an hour in the timeline for a proper post-proposal engagement session? Bobby, you are quite the gentleman! Okay, enough talk...let's get to the photos!

Oh, the Naked Cowboy - a staple in Times Square. In case you are wondering, yes he does continue to be the Naked Cowboy during the winter. My friend and I took a photo with him in which we are both wearing huge heavy coats, and he is wearing...this.

Lisa's parents and I waited inside AΓ©ropostale so we would go unnoticed until the big moment. The fun part was explaining to the store attendant why I was seemingly stalking these people through the store window. Also, I love that the musician was dressed as an old-school Italian waiter - fake mustache and all!

After the proposal, we walked around the corner to Bryant Park. I loved the views and the trees and the people reading on the lawn and the people playing chess. There was such a strong sense of community for supposedly being a tourist attraction!

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Cassi Claire is a New Jersey & Destination wedding photographer
that specializes in vineyard, estate, and castle weddings!