The Sweet Life of Diandra

Winter Garden’s sweetheart, Diandra Culver, decorates life with cupcakes, color, and community—and a whole lot of gratitude baked in.

Text: Rheya Tanner

Sugar, color, and glitter— so much edible glitter, of every shape and shade you can think of—are what make up the spirit of lifelong baker Diandra Culver. She is an unabashed lover of all things sweet; and for Culver, nothing is sweeter than a cupcake. “Cupcakes are simple, but can be taken in so many directions. They’re just something small and fun that you can take with you wherever you go.”

Culver first fell in love with baking when she was a child, though her motivations were more straightforward. “I loved sugar!” she says. “My mom called me a ‘Carbo Queen’ because anything with carbs and sugar was my thing.”

There was also the messy, hands-on aspect of baking that children are naturally drawn to. “Most of the time, kids want to use their own creativity, and make their cupcake exactly how they want it.” It was only a matter of time before Culver would combine her love of kids and creativity with her love of cupcakes—a marvelously messy concoction that came to be known as Sweet Dee’s Cupcakery.

People of all ages pay her a visit to satisfy their sweet tooth, but Culver’s first and favorite focus is on the children. “I’ve always had a passion for kids,” she says. “That’s why I added the cupcake bar to the bakery. I wanted to have that special connection with kids.”

The bar is lined with sweets of all stripes, from chocolate chips to gummy worms, where children can design their own dessert. “I have kiddos who get the exact same thing every time, but just love to make the cupcake. I think it’s just the cutest thing.”

Culver and her husband have been trying to have a child of their own for over a year. “There were complications,”

says Culver. “They were trying to figure out what was wrong, and we ended up finding out I had PCOS.” PCOS, or polycystic ovarian syndrome, is a hormonal disorder that affects the ovaries, causing a variety of symptoms, including fertility issues.

But Culver has only ever faced the messes of life, business, and baking with a smile. For her, it’s all just part of the process. “There are so many little things that stick out to me as a sign,” she says. “My lucky number is 21—it’s the day I was born, and it’s the building number for the shop. A lot had to line up for it all to work, and it somehow did.”

Even as the world around it changes, baking is one of those rare things that remains ever the same: measure, mix, heat, repeat. It is that legacy that Culver has infused with her own flavor and shared as a cupcakey connection to the community.

Starting From Scratch

A teenaged Diandra holds up her first cake.

Courtesy Diandra Culver

Culver’s love for the practice of baking (as opposed to the eating) started with encouragement from her next-door neighbor. “She had a dream kitchen—double ovens, a closet full of every Wilton product under the sun. Anything I wanted to experiment with, she let me. She taught me all the techniques she knew. I was with her any chance I got.”

Culver was a sporty, athletic kid, spending her childhood either figure skating at the ice rink, or at the ballpark. “My dad owned a baseball school in Central Florida for a long time, so I basically grew up in his batting cages,” she says. ‘Still, baking persisted as a hobby. “My best friend and I were obsessed with “Cupcake Wars’ and we would do our own cupcake competitions. We brought our cupcakes to the ice rink and let the girls decide the winner.”

In college, baking was sidelined in favor of moving to Mississippi for a degree in park and recreation management. She taught girls’ figure skating there as well, where out of the blue, baking found her once again. “One of my girls’ moms owned a bakery, and I started working for her part-time,” she says. “They were actually one of the sponsors for the hockey league; we’d pick a random seat in the arena to win cupcakes courtesy of her bakery. And I didn’t even know her yet!”

Culver says that was where her connection to cupcakes was cultivated. “She gave me a lot of flexibility, as long as the work got done. I baked for friends’ birthdays and other occasions, and used those to try new things and share my love for baking.”

I have kiddos who get the exact same thing every time, but just love to make the cupcake. I think it's just the cutest thing.

In her junior year, she met Dustin, a civil engineer and the love of her life. "He was a local, so he never stayed on campus. And when we first started talking, we realized we had a whole circle of friends in common. The rest is history."

The two stayed in Mississippi for five years, but Diandra’s heart was set on returning to Florida. “I knew I wanted to be here. It was just a matter of Dustin, who grew up in Mississippi, and all his family is there.”

What ultimately brought her back was a job at Disney. “I had to do an internship to complete my degree, and the internship turned into seven years,” she says. “I was a recreation coordinator for the water parks and then for the Polynesian.”

But Culver felt dissatisfied and started planning her next career move. “I didn’t feel like I was growing, and decided I wanted to do something for me.”

And there baking was again, waiting for her like an old friend.

Mixing It Up

Diandra Culver in front of the Sweet Dee’s storefront

Photo by Fred Lopez

Easily the best part of baking, according to Culver, is the artistry. “I’m not an artistic person whatsoever,” she says. “I can’t draw a picture of a cake. But putting an idea onto a cake is totally different. No two cakes are ever the same. You can always do something new.” This, evidenced by the Cupcakery’s 15 flavors, two of which change weekly depending on the season and the whims of the staff. “I give the girls a lot of creative freedom. We love to check all the random holidays, like, ‘It’s Harry Potter’s birthday!’ and figure out how to make a butterbeer cupcake,” she says. From there, everyone samples tester recipes and gives a yay or a nay.

Especially when you own a business, you have to have that balance of work and play.

But more than her own creativity, she loves kids’ creativity, and nurtures it through both the cupcake bar and “Birthday Bakes”— an event inspired by her time at the Polynesian. “In the drop-off centers, we would do a cupcake class. We brought in a goofy French chef character who put recipes in a magic oven. I took that idea and turned it into a class where kids could actually learn stuff.”

As for Culver’s own birthday dessert of choice, she’s not one to bake her cake and eat it, too. “I’m a born-and-raised Florida girl: I want my Publix cake!” she says. “The way people are about my icing, that’s how I am about Publix icing. I do give them some ideas and challenge them to use their creativity as well.”

Finding the Sweet Spot

Diandra and Dustin Culver

Photo by Fred Lopez

When Culver was first contemplating owning a bakery, she credits her husband with giving her the confidence to move forward. “He’s the most supportive thing ever. He literally sat me down and was like, ‘Whatever you want to do, you can do it.’”

Culver describes their relationship as cohesive and full of adventure. “We love to travel and make use of life. Especially when you own a business, you have to have that balance of work and play. If not, the business will eat you alive. So, we spend time together whenever we get the chance.”

The couple’s most recent trip was through Paris, Rome, and Venice. “We got to take macaron classes in Paris, which was a fun experience—mainly for me to watch him, since he’s not as much of a baker as I am!”

The people who come in week after week to try different flavors or just to say hi—they’re a big part of what I do.

Their home base is Winter Garden, though it wasn’t always. “I grew up in Lakeland, but I’d honestly never heard of Winter Garden,” says Culver, recalling the first time she ever came to Winter Garden Village. “So I’m driving through and I’m like, ‘what is this place, and why have I never heard of it?’ And that was before I even discovered downtown.”

Before long, it was home sweet home. "It's so unique. I always tell people it's like stepping back into the ’50s. It’s not like anything else in central Florida.

Eight years later, that love for Winter Garden was both her strongest motivator and her biggest hangup in pursuing the bakery. “I knew if I was going to open a bakery, this was where I wanted to do it. But we all know how hard it is to get into downtown Winter Garden,” she says.

Until one fateful drive through town, when they found their sweet spot. “We saw a For Rent sign in a window, and I was like, ‘Dustin, stop the car!’” Culver says. “We called the landlord immediately.”

In that single day, five other people had already called to express an interest. But the Culvers were the first ones in. “I didn’t even see the space. Dustin FaceTimed me at work to show me. I wasn’t sold on it, but his civil engineering mind already saw the potential.”

Sweet Dee’s Cupcakery opened soon after with four employees. Two years later, Culver has six staff members and a wonderful relationship with the kids and parents who love to stop in. “I’ve seen a lot of kiddos grow up,” she says. One such kiddo is Addison, a young girl whom Culver met when she was just a baby. “I met her family at Halloween fest the week before I opened. We were giving out cupcakes just to say, ‘hey, we’re here.’ And I gave Addison her first cupcake ever.”

Addison, now the unofficial mascot of Sweet Dee’s Cupcakery, enjoying her first-ever cupcake at a Halloween event downtown.

Addison is now growing up alongside the cupcakery. “Every time she comes in, we do up different cupcakes to match her outfits.” Culver was the proud baker of her first, and now her second, birthday cake.

Community and Cupcakes

“The people who come in week after week to try different flavors or just to say hi—they’re a big part of why I do what I do,” says Culver. “There’s so much hate in the world. But the Winter Garden community feels like your next-door neighbor.”

During the pandemic, she was forced to run the store without staff to stay afloat. But as Covid wreaked havoc on small businesses around the country, Winter Gardeners stepped up in support, buying gift cards to keep the five-month-old Cupcakery afloat. “People who didn’t even know my story cared enough to keep me here,” Culver says. “There were nights I would go home and just cry because I couldn’t believe we were still here.”

I take all these things as learning experiences. They’re not fun while you’re in them, but then you look back on it and you’re just like, ‘that really did have to happen.’”

The city was a major supporter as well, in offering help and creating curbside parking when restaurants could only do takeout.

“When outdoor dining came back, they shut down half of Plant to put in tables. I feel like, if it were anywhere else? That would not have happened.”

Choosing to open in Winter Garden, while it wasn’t easy, turned out to be the best possible move. “I’m so grateful to this community. None of this would have happened without them.”

One in the Oven

Culver is grateful for so much: her husband, her staff, and her community. On top of that, though, she is grateful for the next chapter in her life. With the publishing of this issue, Diandra and Dustin officially announce the arrival of the newest Culver. Diandra is pregnant!

Dustin and Diandra's pregnancy announcement photos, taken while in Europe.

Courtesy Diandra Culver

The couple found out just before their trip to Europe. Her PCOS diagnosis was, fortunately, what gave her access to the treatments she needed. “It happened rather quickly after that!” Their official due date is April 18, 2022. Despite all the messes that stood in her way, Culver remains as vibrant and optimistic as she’s always been. “It’s a blessing,” she says. “I take all these things as learning experiences. They’re not fun while you’re in them, but then you look back on it and you’re just like, ‘that really did have to happen.’ Everything happens for a reason.”

Some things never change.