An Olive Proposal
Leslie + Caleb
Some love stories take a detour before they find their way. Leslie gave Caleb her number, he never called, and fate handed him a second chance at a softball tournament months later. What followed was a first date at a historic fort, a proposal gone beautifully sideways, and a ring that looks exactly like their love, simple and completely theirs. This is Leslie and Caleb's story, and we're honored to be a small part of it.
the love story
Leslie was living in Texas in 2024 when a mutual friend floated an idea: there's this guy Caleb, he's single, you two might be a great match. Leslie said sure, go ahead and pass him my number. Caleb never called.
Fast forward to February 2025. Leslie had moved back to Florida and joined that same friend at a men's softball tournament. Caleb was playing. He recognized her immediately, felt too nervous to say anything, and a little embarrassed about never calling. He was not going to make the same mistake twice.
That night, he worked up the courage, called her, and asked her out.
Their first date was at Harry's in St. Augustine, followed by a walk around the historic fort. They talked about everything: their shared love of softball (Leslie played in college), Caleb's obsession with The Andy Griffith Show and all things black and white TV, and the kind of life partners they each hoped to become. The connection was instant and unmistakable. They've been inseparable ever since.
But the moment Leslie knew he was different wasn't romantic, and it wasn't a grand gesture. It was the first time he handled her attitude like it was nothing. She made a sarcastic comment, fully expecting him to get flustered or defensive. Instead, he smirked, fired one right back, and kept the conversation moving like it was his natural habitat. Effortless. He understood her humor, matched her energy, and didn't take a thing personally.
Oh… you're not scared of me. Noted.
Anyone can handle the cute moments. But someone who can handle the spice? That's a keeper.
the proposal
Caleb had a plan. Or so he claimed.
He told Leslie they were heading to the museum and then to Ruth's Chris with his cousin, since she had tickets and a gift card from work. Totally believable. Leslie didn't think twice.
They got to the museum, and something immediately felt off. Caleb kept walking her in circles, stopping and starting, pretending to look at things they'd already passed. What Leslie didn't know was that he was desperately searching for the rug his cousin was supposed to bring for him to kneel on. Leslie, tired and confused, finally asked him what on earth was wrong with him.
He just looked at her. That defeated, forget-the-plan look.
And in that split second, she knew exactly what was happening.
She threw her phone. She screamed. She jumped up and down. And she said yes before he even finished the question.
It wasn't planned, and it wasn't polished. It was completely them, and it couldn't have been more perfect.
the rings
Leslie's ring is the Libby by Olive Ave. It's simple and classic, with plenty of personality. She's always gravitated toward pieces that feel timeless rather than flashy, and she wanted something elegant and environmentally conscious. Nothing huge, nothing loud, just something that felt true.
When she looks at it, she sees exactly what she and Caleb have built together: sweet, steady, a little silly, and completely their own.
They say it to each other all the time: they hope they never forget how easy it is to love one another. No matter the season, no matter how busy or chaotic life gets, loving each other has always felt natural. Never forced, never complicated, just genuinely easy. And on the harder days they know will come, they hope they remember that. Because holding onto that truth makes even the tough moments feel a little lighter.
Inspired by their story?
Every love story deserves to be worn. Whether you're starting from scratch or building on something meaningful, Olive Ave makes it possible.
