With Valentine’s Day here, we’re thrilled to officially announce the winners of Wed Society Delaware + Eastern Shore’s 2026 Looks of Love contest.
After weeks of heartfelt submissions and a bracket-style Instagram Stories voting competition, our community has spoken — and Megan & Kevin have captured the title of this year’s Looks of Love champions.
As our winning couple, Megan & Kevin will enjoy a romantic overnight getaway at the Addy Sea Historic Oceanfront Inn in Bethany Beach, graciously sponsored by Addy Sea, complete with champagne and a gift card for dinner — the perfect Valentine’s escape.
We also want to give a special congratulations to our runners-up, McKayla & Clay, whose sweet surprise proposal by the sea earned an incredible wave of support from our community.
Scroll below to revisit all eight beautiful love stories that made this year’s competition so special.
A heartfelt thank-you to our generous sponsor, Addy Sea Historic Oceanfront Inn, for making this unforgettable Valentine’s getaway possible.
Winners! MEGAN & KEVIN
Crystal Finnegan Photography
Megan and Kevin first met as childhood neighbors — when she was two and he was six — their lives quietly overlapping for years without ever forcing the timing. It wasn’t until college that something shifted, as weekends together and long conversations slowly became constant.
Life unfolded naturally from there: shared homes, rescued dogs, and building a life rooted in patience and partnership. When Kevin proposed at a Maryland winery, Megan cried, laughed, and immediately announced she had to pee — a perfectly human moment in a love story built on steadiness rather than spectacle. Grounded and deeply familiar, theirs is a love that grew exactly the way it was meant to.
Runners-up: MCKAYLA & CLAY
Christopher J Hawk Photography
McKayla and Clay met through a mutual friend in 2021 and quickly realized they had found something special. From the beginning, their relationship was grounded in kindness, selflessness, and a sense of ease that made life feel better together.
Over the years, they built their first home, welcomed two beloved dogs, and created a life rooted in care and commitment. What McKayla thought was a Christmas photoshoot on a cold Rehoboth beach turned into a proposal — a quiet, meaningful moment that reflected everything they’ve built side by side.
EMILY & HUNTER
Lindsay Monahan Photograohy
Emily and Hunter’s story is rooted in a lifelong familiarity. The two met in preschool and grew up in the same community, their paths crossing for years through school, church, and hometown traditions. After graduation, life pulled them in different directions — until Hunter returned home nearly a decade later and re-entered Emily’s life at a birthday celebration.
Days later, Hunter left Emily a voicemail she would never forget: “I didn’t want another ten years to pass before asking you on a date.” What followed felt both new and deeply familiar, proving that sometimes the best love stories are the ones that have been quietly unfolding all along.
MARY & GARRET
Alex at The Paris Photographer
Mary and Garret met with a right swipe on Hinge in the middle of the NYC hustle, fully expecting something low-key and casual. That plan quickly unraveled when Garret asked Mary out just before moving into a fourth-floor walk-up — proving his commitment one heavy piece of furniture at a time.
Their relationship grew alongside city life, balancing long staircases, late nights, and the energy of New York. Garret later proposed at a candlelit spot overlooking the iconic skyline before the two traded subway commutes for Delaware life — bringing their big-city grit (and their Bernese Mountain Dog, Hudson) with them. From Hinge dates to heartfelt milestones, their story blends romance, humor, and adventure.
CLAIRE & HUNTER
Heather Baker Photography
Claire and Hunter met during the height of White Marlin Week — she bartending at Sunset Grille, he working as a mate on a charter fishing boat. From the moment Hunter spotted Claire carrying a tray of drinks through the crowd, he was determined to get to know her, ordering mudslides simply because they “took longer to drink.”
The two quickly became inseparable, and just months later, on an ordinary Tuesday in January, Hunter proposed — completely catching Claire by surprise. Their story is filled with bold first impressions, intentional pursuit, and moments that felt inevitable from the start.
LAUREN & JOE
Ash Elliott Photography
Lauren and Joe crossed paths during one of the most difficult weeks of Lauren’s life, while she stayed by her mom’s side in the hospital where Joe was part of her care team. After her mom’s discharge, Lauren shared a photo thanking the medical team — and weeks later, Joe followed up to check in.
What began as a simple message turned into long conversations, shared experiences, and a growing connection across cities. When Joe invited Lauren to a first date at one of her dream restaurants in Chicago, it marked the start of a relationship built on empathy, intention, and showing up for one another — often when it mattered most.
ALEXANDRIA & LANDEN
Jessica Mooney Photography
Alexandria and Landen’s love story began years before either of them knew it would last. The two first met in high school through mutual friends and briefly dated before life sent them in different directions. Years later, fate stepped in quietly when Landen unknowingly opened the door for Alexandria at an event on his family’s farm — an awkward moment that quickly became unforgettable.
They reconnected soon after and built their relationship through everyday life: snowstorms that turned into extended stays, career changes, family trips, and the routines that come with truly growing together. On Christmas Eve 2024, Landen proposed in a moment that was perfectly unscripted — at home, in pajamas, with laughter, happy tears, and a ring that turned out to be two sizes too small. Imperfect and heartfelt, their engagement was a reflection of the life they’ve built side by side.
BREANNA + NICO
“You two would be so cute together,” a best friend predicted when she introduced them at community college more than a decade ago. She wasn’t wrong.
Last winter at Schellville, they watched a public proposal unfold, and she mentioned she’d want something more private — just the two of them. Two weeks later, on a freezing Christmas Eve morning, he insisted on a snowy hike she didn’t want to take. Along the quiet trail, he reminded her of that conversation before getting down on one knee, proposing exactly the way she had hoped. They later celebrated with a Caribbean cruise, marking the start of a new chapter more than ten years in the making.
Thank you to everyone who submitted their love stories and to our incredible community for voting, cheering, and celebrating these couples along the way. Each story reminded us why we love what we do — highlighting real, heartfelt connections right here in Delaware + the Eastern Shore.
Happy Valentine’s Day from all of us at Wed Society. ❤️
