After meeting at the Salty Dog Saloon, Connor and Olivia's very first date was at one of Olivia’s sorority date functions—a decade-themed night full of fun, dancing, and just the beginning of something special.

Just two weeks after their very first date, Connor took Olivia to Charleston for his fraternity’s formal.

Connor asked Olivia to be his girlfriend on a date at St. Augustine beach...she said no.

While watching Connor McDavid and the Edmonton Oilers defeat the Calgary Flames in the game 5 overtime thriller, Olivia asked Connor to be her boyfriend. (She had been wanting to for weeks but was too nervous.) He said yes!

Connor and Olivia spent a sunny summer together in Gainesville, taking classes and making the most of student life. While Connor worked toward his master’s, Olivia hit the books to study for the LSAT. This photo was taken on the Fourth of July at a darty—a fun break from the books and a favorite summer memory!

Connor and Olivia spent their first fall semester together at UF making memories with Gators football, hockey games, and Greek-life events. This photo was taken at Olivia’s sorority semi-formal—just a few days before they said “I love you” for the first time (Olivia said it first!).

Connor and Olivia spent their first holiday season together soaking up all the festivities. This photo was taken on New Year’s Eve, when Connor took Olivia out in Tampa with their close friends Noemi and Quinn— a bridesmaid and groomsman! Who would’ve guessed the four of them would be celebrating again, side by side, three years later at the wedding?

Connor and Olivia graduated from undergrad at the University of Florida, wrapping up an unforgettable chapter. During their spring semester, they set sail on a spring break cruise to the Bahamas and toured several law schools along the way. After weighing all her options—and with a little help from Connor—Olivia decided to continue her journey at UF Law. Go Gators, again!

During Connor's family's vacation, the couple explored the beauty of Italy and Switzerland together—that’s amoré! From the winding canals of Venice to the cliffs of Cinque Terre, the art of Florence, the elegance of Lake Como, and the charm of Zurich, it was the trip of a lifetime filled with pasta, gelato, and plenty of memories.

In the fall of 2023, Connor and Olivia were back in the Swamp—cheering on the Gators, hitting the books, and soaking up life in Gainesville. This photo was taken during a well-earned celebration: Olivia had just wrapped up her first semester of law school, and Connor was officially halfway through his master’s program.

Connor and Olivia spent another holiday season together, making festive memories with friends and family. This photo was taken at St. Augustine’s Nights of Lights alongside their couple-friends Mel (a bridesmaid) and Hunter.

This weekend, Connor and Olivia got to celebrate Brendan (Connor’s brother and best man) and Carli (one of Olivia’s bridesmaids)—as they got married in Sarasota. It was such a special weekend filled with love, laughter, and happy tears. Olivia is so excited to officially gain a brother!

Connor proudly served as captain of UF Club Hockey, leading the team to a National Championship win! Olivia was there every step of the way—cheering him on throughout the season and celebrating this incredible victory by his side. This was a moment and a celebration they’ll never forget!

After a trip to Australia, Connor surprised Olivia by flying home early because he missed her—and had an even bigger surprise in store. He planned a belated birthday weekend for her in St. Petersburg, complete with a beach getaway and all of her best friends there to celebrate. That summer, the two tried to visit each other every other weekend… but pretty quickly, it turned into every weekend. Connor was living at home in Lakewood Ranch, while Olivia was interning with a law firm and a federal judge in Tampa. Between beach days, dinner dates, and playing pickleball, it became one of their most special summers yet.

Connor took Olivia for the first time to Connor’s family cottage in Ontario, Canada—a place that’s been in his family since the 1950s. They canoed across the lake, swam together, went on long walks, and ended each day around the campfire and watching stars.

Connor and Olivia took a trip to Austin, Texas to visit their friends Patrick (a groomsman) and Aliza. They explored the city, attended a rodeo, ate a lot of BBQ, and cooled off with a swim at Zilker Park.

In the Fall of 2024, Connor and Olivia spent their weekends cheering on Gators football. That October, Connor started his job at Deloitte in Tampa, while Olivia continued into her second year of law school.

This photo was taken during what Olivia thought were just her family Christmas card pictures. But Connor had something much more special planned. In the middle of the shoot, he got down on one knee and asked Olivia to marry him—and she said yes! Completely surprised and overjoyed, Olivia was even more touched to find both of their families waiting to celebrate over dinner that evening. It was the easiest yes, and the beginning of forever.