Orlando wedding, engagement, family photographer | Root Photography Blog

Natalie swiped past the cute golf guy three times on Hinge because Lake Mary was “too far” from Winter Garden, she finally accepted a match with Jack on a different app!

The first thing he ever said to her was “Happy Fourth of July, Natalie!” They went on their first date in Winter Park, proving there was a middle ground between Winter Garden and Lake Mary! They enjoyed a three hour dinner and never ran out of things to say, and Natalie drove home with Taylor Swift’s swooniest songs on full blast! They waited ages until their next date- oh, just kidding! The very next morning, Jack played an early round of golf in Winter Garden. He and Natalie closed down a coffee shop and had their first kiss in the parking lot.

When it came to proposal time, Natalie was very aware it was coming. They’d gone ring shopping and Natalie even knew Jack had the ring in their house! With a trip planned to Pennsylvania, Natalie’s hometown, they even talked about how that was the perfect time for Jack to ask her dad’s permission. So it came as a huge surprise when the week before that trip, Jack appeared nervous before a casual dinner with friends. He even asked Natalie to change her dress before they left because they wouldn’t coordinate with the one she was wearing!

On the walk up to the Yacht Club, Natalie knew something was up and started scoping out his pockets. She squeezed his butt and felt a box, and insisted he can’t propose before their trip; her dad would be so mad!! He explained her dad had come to Florida for a work trip a few weeks before so they already had their big talk. Jack walked Natalie to the wedding gazebo which was set up with roses and candles, and Jack officially proposed. ✨