With Valentine’s Day here, we’re so excited to officially announce the winning couple of Wed Society Tampa + St. Pete’s annual Looks of Love contest! There’s truly nothing more heartwarming than reading a love story and seeing the beautiful photos that capture the special bond between two people.
Over the past few weeks, our community voted and celebrated the incredible couples who shared their stories with us — and after an amazing round of voting, we are thrilled to introduce your 2026 Looks of Love winners…
Congratulations to Our Winning Couple: Megan & Wesley!
Megan & Wesley
Photo: Yvonne Gougelet
Megan and Wesley met over three years ago while working a music festival in Modesto, California. After staying connected, their relationship quickly grew into a long-distance romance, and six months into dating Wesley moved from Arkansas to Tampa to be closer to Megan. The couple got engaged two months ago and are excited to spend the rest of their lives together, forever thankful that music and their creative paths brought them together!
Jaileen & Daniel
Photo: Miranda Doughty
Daniel and Jaileen’s story began in elementary school, where they first met and grew up side by side, always staying connected through their younger brothers’ close friendship. It wasn’t until high school that their friendship turned into a relationship during Daniel’s senior year and Jaileen’s junior year. After three years of long distance while Daniel played college baseball, the two returned to their hometown of Tampa to pursue their careers. On January 3rd, Daniel proposed in their favorite place, St. Augustine, and they’re excited to begin this next chapter together.
Gabby & Riley
Photo: Bailey Uerling
Jackie & Connor
Photo: Matt Power Photography
Rheannin & Brett
Photo: Natalie Maria Photography
Brett and Rheannin met on Hinge in January 2020 during a season of major life changes, with Rheannin moving to Nashville and Brett returning home. Their first date took place the very day she moved into her apartment—before the boxes were even unpacked. As a frontline healthcare worker and with Brett transitioning to remote work, the two navigated the challenges of the 2020 pandemic together, emerging even stronger. In 2023, Brett’s new job brought them to Tampa, a place they now proudly call home. On February 27, 2025, during a winter trip to Evergreen, Colorado, Brett proposed on a frozen lake—turning a simple getaway into the start of their forever.
Bethany & Joe
Photo: Bespoken Forever Photography
Nicole & Ryan first met in 2021 at Crunch Fitness in Downtown Tampa, where they both worked out regularly—and still do to this day. After noticing each other in passing, Ryan replied to one of her Instagram stories about the gym, sparking a conversation that eventually led to their first date: brunch and a pool day that August. They’ve been inseparable ever since, bonding over their shared passion for health, fitness, and always pushing each other to be their best.
The couple also shares a love for cruising, having taken six trips together. In November 2025, during a Royal Caribbean Utopia of the Seas cruise, Ryan proposed at Giovanni’s on a private terrace overlooking the boardwalk after a week of unforgettable adventures in the Bahamas—made even more special with her mom there to witness the moment.
Thank You for Celebrating Love With Us!
To every couple who entered, voted, and shared their stories, thank you for making this year’s Looks of Love so special. We loved celebrating each of you and can’t wait to continue sharing beautiful love stories with our Wed Society community.
