August 28th, 2024 - Isaac had planned on asking Olivia out at the Idlewild Young Adults group that meets on Tuesday nights (where they first met years prior), but she wasn't there on Aug. 27th. So, he found her on Facebook and sent a text through Messenger asking for her phone number, and yes, you can believe he used a cheesy Christian pickup line. After she gave him her number, Isaac finally mustered up enough courage to ask Olivia out on a get-to-know-you-date, saying right before he called, "This call could change my life."

September 7th, 2024 - Isaac and Olivia met at a Chili's to talk and it lasted 3 and a half hours. They talked about their childhood, hobbies, family, careers, and past education. After the evening was over, Isaac went back to his parent's house, sat on the chair, teared up, and said to his mom "She's the one I want to marry!" His mom responded, "Well, it must have been a good conversation then."

October 12th, 2024 - Right after Hurricane Milton hit Florida, Isaac had the intention of going to a local park to ask Olivia to start a courtship. Once they arrived at the park, the gate was closed because of the hurricane damage and Isaac was internally panicking. He quickly redirected the conversation to focus on how "we make plans but God directs our footsteps, " and started praying for a place close to the water to ask Olivia. As he awkwardly started driving around Tampa, in a desperate attempt to find a place, he noticed a little park with benches near the water. So, he pulled in, they sat down, and after a Bible study about what love is in 1 John he then proceeded to ask Olivia to enter a courtship and she said yes! Although Isaac's original plan didn't quite go as planned, God provided.

February 14th, 2025 - Isaac planned a day full of activities that focused on spending quality time with Olivia for Valentine's Day. They started around 9 am, with Isaac giving Olivia a stuffed bear and asking her to be his valentine, she said yes! As they began their journey for the day, Isaac had prepared a riddle for every activity and meal. As they strolled through the day, they found themselves at the beach for a sunset, a thing they both thoroughly enjoyed. As they reflected on their 4 months of courtship, they realized all the more that they both wanted to be married to one another. So, while no ring was given, they both checked their calendars and chose October 18th to be their wedding day.

April 19th, 2025 - After valentines day, Isaac started planning a time to propose. Olivia's younger sister, Julia, offered to help with the planning, so through a 60+ email thread of communication for almost 2 months they planned the perfect day. Isaac took Olivia to Clearwater Beach to watch the sunset, walked down close to the water and asked Olivia to marry him. She said yes!!! Right after that, Julia came from behind, having filmed the proposal, and took the engagement photos, which was a complete surprise to Olivia. Shoutout to Julia!