Gabourey Sidibe first wore a wedding dress and walked down the aisle long before she was engaged: In 2013, the Oscar-nominated actress, author, and director helped Jimmy Kimmel's now-wife Molly McNearney pull off the ultimate big-day prank. Instead of the bride walking down the aisle at the start of the ceremony, Gabby, outfitted in a classic white wedding dress and long veil, made her way towards the altar, much to the confusion of both Kimmel and the couple's guests. "It sounded fun," she remembers of being asked to be part of the experience, "but it was not as fun as it sounded. I had to try on a bunch of dresses, but it wasn't as serious as it feels now."
Now that Gabby is planning her own wedding to fiancé Brandon Frankel, head of partnerships at NoCap, she's spent quite some time thinking about what her perfect celebration looks like, and the plans—from the fashion to the setting—are shaping up to be anything but traditional.
When Gabby was a child, her mother worked as a wedding singer, and that meant the actress and her brother frequently went along to the reception. "I was definitely one of those uninvited children at a ton of weddings—and I actually hate them because of it. In my life, I have vowed to go to four more including my own," she half-jokes.
Considering the fact that her own will be one of the last weddings Gabby plans on attending, it's going to have to be a good one. Although the couple is still deciding what, exactly, their celebration—which they say will take place sometime in spring of 2023—will look like, the bride-to-be does have a sense of what will and won’t be included. "The entire time we have been engaged, I've always been like, ‘No, we shouldn't have a wedding.' Maybe we'll throw a barbecue, get married in the bathroom, and then we’ll come out and tell everyone we're married," Gabby says.
There will be no bridesmaids and no bachelorette party, or "any other normal wedding things," Gabby shares. "It cannot be a traditional wedding. Really, it can't be. I don’t want anything done the 'traditional' way. Our relationship is very much on our terms and I want it to be fun, like a true party."
The hands-on couple does intend to tackle as many wedding-planning tasks as they possibly can. Brandon says, "We like to outsource, but we're both very involved in everything we do. We're creative people and we're both pretty good at executing, so we'll have someone [helping], but we'll definitely be super involved."
"There's a lot I don't know how to do," Gabby admits of wedding planning. "How do we get cake at a wedding? I don't know!" What she does know is that she can rely on Brandon's support in the months leading up to the wedding and well beyond.
"To me, weddings are very different from marriage and partnership," Gabby says. "I think I always, always wanted there to be a partner in my life, [but] I didn’t know what he was going to look like or what he was going to be like at all."
For a long time, Gabby simply didn’t believe a lifelong partnership was something she could hope for. "I just couldn't fathom what [the right] partner for me actually felt like," she says, and that's largely because she couldn't envision a future with the people she had shared previous relationships with. "I couldn't imagine dating someone I actually liked. Turns out, totally possible! So, I'm really happy to have been wrong about where I saw my life going, partnership-wise. [Brandon] is an incredible, incredible partner."
Brandon's path towards love was different: He had been married once before, in his mid-20s, but the relationship didn't work out. Suddenly, he had to rethink everything he previously knew about finding a partner in his 30s. The dating landscape has become largely digital, and it wasn't something Brandon was sure he was ready for. "I never internet dated or or had to use any of those apps," he says. "I told myself, ‘I'm out. I’m done. I'll retire.'"
Luckily, he decided to give modern-day dating a chance and downloaded Raya, an exclusive, members-only dating app popular among the celebrity set. Brandon's approach was to swipe "Yes" on everybody, while Gabby, who had only just downloaded the app the day before the duo matched, swiped "Yes" only on him.
After messaging back and forth for a bit (Brandon admits he did initially worry he was being catfished), the pair eventually met for their first date, which Brandon says lasted for "more than seven hours."
There was an immediate spark, but it took Gabby a little time to fully let Brandon in. "I have a real fight or flight personality," she explains. "I was kind of dodgy and scared quite a lot in the very beginning of our relationship. [Then, during the pandemic] I just started trusting him. I really realized that like, this guy's not going to disappear, you know? And my big fear was that, if I loved him, he would just poof and disappear. So, I was playing my cards very close to my chest."
Once Brandon was in, he was in for good. By October of 2020, he knew he was ready to propose and worked with Seattle-based jeweler Pendergast & Painter to create Gabby's dream engagement ring, which she thought was a princess-cut diamond. "Spoiler alert: She didn't know what that was!" Brandon laughs. "I picked out a stone and went through all this insanity for months…only to find out that she actually wanted a round brilliant diamond."
So, he revised his design and spend the next eight weeks planning what was meant to be the perfect surprise proposal—the only problem was it was never going to be a surprise at all.
"Basically, we share this 'trap phone' if you will, and I wanted to take a picture of the first conversation we had on Raya because you aren't allowed to take screenshots on the app," Gabby explains. "So, I take a photo and go into the gallery and there are only three photos in there—the one I took and two of this really pretty ring. I literally screamed."
As if it wasn't enough for Gabby to have seen the ring in advance, she also saw the entire proposal setup, complete with "a huge ‘Will You Marry Me’ balloon situation happening, rose petals on the bed, and everything," Brandon says. He had made one small misstep: In an effort to create the perfect proposal space, he chose to leave a light on so the room would be romantically lit when he popped the question. Gabby, who noticed the light shining beneath the door, went in to shut it off before leaving the house and effectively ruined his carefully-laid plans.
"[The day of my proposal] I was completely in the dark—and it would have been a really, really great surprise if he didn't leave the light on," Gabby laughs. The one detail Brandon was able to surprise her with? He incorporated the couple's shared cats into the mix, outfitting one with a collar and tag that read, "Will you marry my daddy?"
Today, the couple can look back on the moments that went wrong and laugh. After all, the most important detail of the proposal—Gabby saying yes—went exactly to plan. Now, they’re pivoting their focus and thinking about the future.
Style is important to Gabby, and she's taking her wedding dress search seriously after experiencing the "power" that comes along with wearing a bridal gown. "I started trying on dresses [at the shoot] and I was like, ‘Oh! Oh! I got it!' There's some power in stepping into a wedding dress, and now I need more wedding dresses!" she laughs.
Initially, a formal wedding dress didn't seem like something that would make a difference to her one way or the other, Gabby explains, but this shoot changed everything. "I have had other days where the attention is on me and I feel like a princess, so I didn’t think it was going to be that big of a deal, but it was actually really great."
The burning question is, knowing that tradition will be cast to the wayside, what will Gabby wear down the aisle? Forget about classic white fabrics and traditional dress shapes; the bride-to-be is leaning heavily toward bold color palettes and prints, unexpected silhouettes, feathers, and oversize jewelry, similar to what she wore to cover our Style issue.
"I’m super against tradition," Gabby adds. "I definitely don't need a white dress. My favorite look [from the shoot] was the pink African print. Honestly, whatever I wear on the wedding day will probably be African print. It might have a little white, so it looks like a wedding dress, but it's definitely going to be colorful."
"I've been pulling a lot of things on my Pinterest board to share with my stylist, but my biggest muse has been Danielle Brooks. She had two beautiful dresses—one created by Christian Siriano, who I've also worn before. When the time comes, I am definitely going to hit him up to create a custom look, maybe even African print," she explains.
Brandon's big-day fashion will also be a priority—Gabby says that seeing her future husband dressed up for their cover shoot ("He usually wears tops and sweatpants, athleisure," Gabby explains) was another powerful, affirming moment for the couple. "Seeing him in a suit just made things real for us," she adds. "That day was really incredible. It also made me think, 'Oh, I want everybody there! I really want to celebrate this.' I want everyone that I love to be at our wedding now, when I used to always say just 20 people tops."
His signature style? Simple and sleek attire paired with what Gabby lovingly calls a "peacocky moment." "I'll wear one piece of flare with a bunch of pretty plain stuff," Brandon explains. And after seeing how much he liked the colorful attire at our shoot, he's open to revisiting those type of looks for his own wedding. But it's his shoe game that everyone should watch closely: "I'm a sneakerhead," Brandon admits, adding that he owns more pairs of shoes than Gabby does.
Style encapsulates so much more than just fashion, and Gabby already has big ideas for her entire bridal look, including her wedding-day glam. In terms of hair, she's leaning towards Senegalese twists or cornrows with a little tiara. "I want lots of jewelry in my hair. I also want beautiful eye makeup with very, very long butterfly eyelashes and a very bold lip," Gabby says. Simply put, she's going to make a statement.
As for the where, Gabby and Brandon haven't finalized this detail just yet, but the couple has ruled out what most couples would consider a classic wedding venue. They love the idea of tying the knot at a private residence, much like the house they shot at in Malibu, where their guests will be able to spend the entire weekend. A view of the water is another wishlist item, but the only non-negotiable the duo has is the time of day: "I want to get married at golden hour," Gabby affirms. "I just want it to be picturesque."
The pair intends to mix their cultures—Senegalese, American, and Jewish—into the entire celebration. "Including my culture [in the wedding] is important to me for sure. I've been feeding him some Senegalese food in the last few years—especially in the pandemic," so a specialty menu is definitely on the table. Brandon's background most certainly won’t be forgotten, either. "It will be a nice mix of African and Jewish touches," Gabby adds. "I want his background to absolutely be there because this is a partnership."
They also know that they'll write their own wedding vows—or make them up on the spot—rather than recite traditional promises. "When Brandon is out of town he does cute things like leave me little love notes and leave messages on our Ring [security system]. We are super communicative with each other—I never wonder about what he’s thinking or how he's feeling about me. So, we will definitely write our own vows or just freestyle at the altar," Gabby laughs.
The last detail that's top-of-mind for the couple is emphasizing privacy and intimacy on the big day. Like so many other pairs, they want their guests to be present for the celebration, not posting on social media. "Maybe we can do those little black phone boxes that they do at Dave Chapelle's show," Brandon jokes to Gabby.
"This is why I literally want 20 people there or like 75 max. Either way, a very, very select number of people who want to celebrate us, not like seeking attention," Gabby quips. "I really think we'll just get married in the kitchen."
Talent Gabourey Sidibe and Brandon Frankel
Photography Erich McVey
Photo Team Dennis Roy Coronel; Matoli Keely
Creative Direction Anna Price Olson
Hair Tara Copeland
Makeup Toby Fleischman
Makeup Assistant Heather Butterwegge
Styling Kelly Augustine
Fashion Assistants Corinne Pierre-Louis; Precious Enaohwo
Production Wonder Serra of Wonder Partners
Booking Talent Connect Group