When moving to a new city, it’s very rare to meet the person you are going to marry your very first week in town; well, sort of…. Josh’s work colleagues convinced him to attend a business networking event his 5th day in Orlando to try and meet new people. He originally didn’t want to go since he had so much unpacking to do from the big move down from New Jersey. After what seemed like countless conversations with all attendees, he finally needed a break, so he decided to head to the rear bar, away from the crowd, for a quiet cocktail. It’s at that moment that Gaby approached him and introduced herself. She asked how he was enjoying the event and his first days in Orlando, since she noticed the words “new in town” written on this name tag on his nicely pressed gray suit with a pink pocket square (Josh’s signature look). The two started talking and getting to know each other and Josh made his first friend in his new city. Gaby is the kind of person that makes everyone feel warm and welcome and from that day forward she strived to invite him out with her and her friends.
For a period of 2 years, they were both dating other people, but when Josh found out Gaby was finally single, he started pursuing her romantically, which apparently wasn’t an easy task. It took Josh over 6 months to finally convince Gaby to go on a date with her. Josh took to her to his favorite restaurant, Prato in Winter Park since many dishes are served tapas style, perfect for sharing the best meatballs in town. Afterwards, they took a stroll down Park Avenue before Josh reached up the courage to kiss her on a park bench by the train tracks. From that day on, they were inseparable.
Even the best planned proposals can go awry when you live in a state with rainy summer season such as Florida. Josh’s original plan included a sunset, romantic lakefront setting, and a photographer to grab the perfect moments of the proposal in disguise. Josh had this planned weeks in advance, since their immediate family and close friends were all traveling to Orlando to celebrate after the engagement, a total surprise for Gaby.
Days leading up to the proposal, Gaby had been sick in bed with a fever and the weather report was showing rain the day of. It looked like the deck was stacked against Josh, and when you are flying by the seat of your pants, nothing sounds more official than a Plan B. Both sets of parents and friends were waiting at the restaurant since dinner reservations were still on, so Josh decided to pivot from the original plan quickly come up with a fitting plan B due to the unfortunate weather circumstances.
Gaby was under the impression they were having dinner with Josh’s largest client and while she was getting dressed, Josh ran out and bought roses, candles, and a bowtie for their dog, Hachi as he was a big part of the show. The benefit of living in a 3-story house was the ability to be discreet two floors below as Josh prepared for Gaby’s grand arrival. As Gaby made her way down the stairs, and came around that last bend, she heard the music and noticed Josh on one knee holding the engagement ring. Gaby was overwhelmed with excitement when Josh bent down on one knee and asked her to marry him. The funniest part of the story was that Gaby came down the stairs holding two different kinds of shoes as she needed Josh’s opinion as to which pair he liked better for their dinner with his client, not realizing a proposal was about to happen. Afterwards they went to dinner where she was surprised to see everyone, but the moral of the story is that life is full of Plan B’s and it was only through pure serendipity that Josh originally met his best friend!