Some love stories are meant to be, and AJ and Jillian’s is one of them. From office coworkers to soulmates, their journey is filled with laughter, adventure, and a deep connection that made AJ’s proposal one for the books. Thanks to Loverly’s Ready for the Ring Contest, this incredible couple is now engaged—with a dreamy 3-carat Whisper Thin® engagement ring from Ring Concierge, a chic look from Men’s Wearhouse, a romantic two-night stay at Islander Resort, professional photography by Emily Prada, and expert proposal planning courtesy of Loverly.
A love that started over music, wine & wanderlust
AJ and Jillian’s story began at work, where their shared love for music, food, wine, and travel quickly turned into an unbreakable bond. What started as office chats soon became the highlight of AJ’s day. Before long, he found himself eager to go to work just to see her—a true sign that something special was brewing.
Their first official date was at a cozy wine bar with live jazz, a cheese board, and a bottle of wine. Sounds like a scene straight out of a rom-com, right? From that night on, they were inseparable.
Falling for forever
For AJ, realizing Jillian was “the one” wasn’t about a single moment—it was about all the little things. Cooking together, walking their dog, sipping morning coffee side by side… Every ordinary moment with Jillian felt extraordinary.
Jillian is absolutely hilarious! She is so beautiful and has a smile that lights up a room. She understands me on a level that nobody else does. What I love most about her, though, is how kind and considerate she is to everyone.
One of their most defining moments as a couple? A big move to Tampa. It came with career changes and uncertainty, but through it all, they faced every challenge as a team—proving that they could take on anything together.
A proposal in the making
When Jillian first spotted Loverly’s Ready for the Ring Contest, she excitedly shared it with AJ (as any eager girlfriend would!). Little did she know, he took it seriously. Seeing the opportunity to give Jillian the proposal of her dreams, he entered—never expecting to win, but hoping for the best.
And then… they won!
For AJ, this proposal was never about the grand gestures—it was about celebrating their love, their journey, and the life they’re building together. He wanted it to be intimate, just the two of them, with a romantic beach setting. AJ gave Loverly creative freedom with the design but loved the idea of roses incorporated subtly into the beach backdrop.
AJ decided to keep the proposal a surprise by telling Jillian that their upcoming trip was a late birthday celebration for him, thanks to a great deal he’d found through their credit card company. Knowing Jillian had been eagerly anticipating a proposal, he even teased her by saying to "be prepared for anything," which kept her dressing up every time they went out—just in case!
For his proposal look, AJ visited Men's Wearhouse, where he tried on various suits before deciding on a custom-fit burgundy suit paired with a plain white button-down. The clean, simple, and classic ensemble perfectly complemented the coastal vibe.
The moment she said “yes!”
On a serene stretch of beach, AJ led Jillian to a breathtaking setup, featuring nearly 300 roses and candles artfully arranged by Foraged Floral Design in a grounded floral crescent. The arrangement was romantic yet subtle, allowing the natural beauty of the beach to shine through.
Emily Prada was the perfect fit to capture AJ and Jillian’s surprise proposal! As a Loverly List winner and a talented local Miami photographer, she has an incredible eye for heartfelt moments. Emily discreetly documented every detail, staying hidden until the big reveal to capture the magic of the surprise.
When AJ got down on one knee, he presented Jillian with a stunning engagement ring from Ring Concierge—a 3-carat Round diamond set in the Whisper Thin® with a Yellow Gold band, Platinum prongs, and hidden halo. Jillian was completely surprised, and couldn’t stop smiling. Their dog, Ralph, even joined in on the celebration, adding an extra layer of sweetness to the moment.
After Jillian said “Yes!” they enjoyed a romantic dinner for two at Islander Resort. It was the perfect moment for AJ to finally share all the proposal planning details he had kept secret for so long. They soaked in the joy, reflected on the special day, and basked in all the happy feelings before sharing their exciting news with family and friends.
A love story that’s just beginning
Now engaged, AJ and Jillian have their sights set on an intimate, romantic wedding in a charming seaside café in Italy—a celebration as unique and special as their love story.
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