Bobby and Rebecca

Bobby's Proposal in Southern New Hampshire University baseball field

How We Met

Bobby: We both work in Insurance in Boston and met at AIG. Started all going out as a big group and once I saw Becca I know we had something special. So things got going and we spent every day together and always have a blast no matter what we are doing and the rest is history.

Rebecca: Bobby and I met at work and after a few months of friendship, it quickly turned into something much more special than a coworker relationship. From the beginning to this day, we love spending every minute possible together, and we have so much fun – the way any best friends do! After two fantastic years together, Bobby decided to seal the deal and ask the question.

How They Asked

It was one of the only nice days in Boston throughout an incredibly rainy April. Bobby had told me to keep my night free for a date night – he was planning on taking me to a restaurant we had never been to before. After work, we got into an Uber together, but instead of ending up at the “restaurant,” I found us driving into Logan Airport. Before I could even ask any questions, I found myself walking out onto the tarmac and approaching a beautiful helicopter.

Moments later, Bobby and I were up in the air, wine glasses in hand, circling and touring our gorgeous city of Boston. We began heading north and after a short period time, Southern New Hampshire University came into view, where Bobby had spent four years on the baseball team.

Where to Propose in Southern New Hampshire university baseball field

I noticed we were descending, and it became clear that we were aiming for centerfield of the baseball diamond. As we exited the helicopter, I saw a small table by the pitcher’s mound with roses, champagne, and a box. Bobby walked me over to it, hand in hand. He handed me the roses, saying the sweetest words, got down on one knee, and asked me to marry him. I instantly said “Yes” and we both immediately fell apart. As we were crying, hugging, and laughing, our families came running out of the press box, giving the absolute best ending to a perfect proposal.

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Special Thanks

Boston executive Helicoptor
The helicopter company that flew us to the proposal designation