Our Wedding Party
Sierra Sessa
Bride
Sierra has waited her whole life for this day, and true to form, she’s planned it with spreadsheets, late-night coffee, and plenty of happy tears along the way. (She cries at commercials, so this was inevitable.) What matters most, though, is simple: marrying her best friend in her favorite place, surrounded by her favorite people. She feels everything with her whole heart, sometimes a little too much, and loves even harder. Equal parts excited, overwhelmed, and endlessly grateful, Sierra is ready for the best day of her life. And once the vows are said, you’ll find her where she belongs: leading the dance floor with joyful tears, contagious laughter, and absolutely zero shoes on. Here’s hoping everyone else can keep up!
Jake Destefano
Groom
Police officer, master of understatement, and the guy who somehow pulled off a proposal without Sierra catching on (a true miracle). Jake is warm, talkative, and always quick with a story or a perfectly timed joke, and if you’ve ever seen him and Sierra together, you know his dry humor is her favorite thing. He’s fully committed to swearing he won’t cry during the ceremony, though no one’s betting on it. He’s the steady to Sierra’s whirlwind, bringing calm, wit, and the kind of love that doesn’t need grand speeches to be felt. Marrying her in the mountains isn’t just a dream come true, it’s something he’s been ready for all along. And when the music starts, don’t be surprised if he holds his own on the dance floor, though keeping up with Sierra is another story.
Jillian Fitzgibbons
Co-Maid of Honor
Jillian has been in Sierra’s life longer than she hasn’t, since they were nine years old, when their friendship sparked something bigger: their moms and nanas became close because of them, and before long, their families blended in ways that still last today. Jill isn’t just Sierra’s best friend; she’s family. She’s been there for every chapter, every heartbreak, every victory, every questionable decision, and every tequila-soaked night that turned into a story worth retelling. Jillian is hilarious, fiercely strong, and deeply sentimental, with a heart of gold and a presence you couldn’t miss if you tried. Sierra has dreamed of this moment since they were little girls, and there’s no one she’d rather have wrangling chaos on her wedding day, or every day after.
Theresa Nickerson
Co-Maid of Honor
Spicy, sharp, and loyal to the core, Theresa has been in Sierra’s corner since they were 12 years old, bonded for life over an unhinged obsession with vampires, werewolves, and love triangles that were way too emotionally intense for middle schoolers. She’s beautifully blunt, wonderfully unapologetic, and never afraid to call it like it is (whether you’re ready to hear it or not). But behind the fire is one of the most fiercely protective, deeply loving humans you could ever hope to have in your life. Theresa has been with Sierra through every high, every heartbreak, and every “what were we thinking?” moment, and Sierra wouldn’t dream of saying “I do” without her standing by her side.
Massimo Sessa
Bridesman
Massimo is Sierra’s brother, built-in bestie, and resident scene-stealer. Flamboyant, fun, and never without a little extra sparkle, he’s the guy who can light up a room just by walking in, and then completely own the dance floor five minutes later. He’s equal parts chaos and heart of gold, with a love for his sister that’s as bold as his personality. Having him up there with Nico makes Sierra’s day complete, and fair warning, if the dance floor turns into a competition, her money’s on Massimo.
Emily Feinstein
Bridesmaid
Emily may have come into Sierra’s life just a few years ago, but it feels like she’s been part of the story all along. She’s the kind of friend you want next to you during a breakup, in a group chat that’s about to get dramatic, or at brunch when you need to laugh until your stomach hurts. A planner to her core, Emily is Sierra’s type-A counterpart in the best way: organized, thoughtful, and always three steps ahead. She tells it like it is, loves hard, and has the rare gift of making the people around her feel braver, stronger, and more seen. Equal parts backbone and best friend, she’s proof that the best friendships don’t always need decades to feel like family. Sierra can’t imagine this day, or the dance floor, without her.
Micayla Kelley
Bridesmaid
Micayla is one of those rare people who shows up in your life, and suddenly you can’t imagine how you ever did life without her. Equal parts sunshine and sarcasm, she’s the friend who would drop everything to help you bury a body or at least arrive with snacks and the perfect pep talk while you plot. She’s endlessly kind, unwaveringly steady for the people she loves, and has a laugh that lights up every room she’s in. Bonded to Sierra forever by a mutual obsession with Harry Potter (don’t worry, no themed bridesmaid dresses… this time), Micayla is joy, humor, and heart wrapped in one. She’s laughter, light, and just the kind of magic Sierra always knew she wanted by her side on this day.
Vanessa Ross
Bridesmaid
Vanessa and Sierra’s friendship began with a twist, but it didn’t take long before she felt like she’d always been there. She’s a total boss in the corporate world, a one-liner queen, and one of the funniest, most genuine humans you’ll ever meet. Equal parts beautiful, sharp, and real, Vanessa is the kind of friend who makes life brighter, louder, and a lot more fun, and Sierra can’t imagine her world without her. She also happens to be Sierra’s fellow dancing queen and resident Mamma Mia! enthusiast, which means if there’s music, the two of them are guaranteed to break it down. The way she slid so seamlessly into Sierra’s life says it all, and Sierra feels so lucky to have her standing by her side on this day.
Courtney Masse
Bridesmaid
Courtney is a total spitfire, a fellow Libra, and one of those rare humans who just gets Sierra. Introduced through her relationship with one of Jake’s best men (the cutest couple, by the way), it was an instant, cosmic-level click that felt less like meeting someone new and more like finding a missing puzzle piece. Courtney has a laugh that makes every moment brighter and funnier, and a warmth that makes everyone around her feel instantly welcome, seen, and at ease. She’s the Quiplash queen, the party MVP, and the kind of beautiful, inside and out, that lights up every room. Just don’t let her near Quiplash and a cocktail... chaos will ensue. Sierra feels so lucky to have her by her side on this day and in life.
Ryan Mills
Best Man
Ryan is Jake’s right-hand guy, professional Jake-roaster, and a certified one-liner machine. If there’s a joke to be made, he’s already made it and somehow made it even funnier with his delivery. But behind all the sarcasm is the kind of friend you can count on for absolutely anything. Ryan has been there for Jake through everything, always showing up with a solid perspective, real loyalty, and maybe… just maybe… an espresso martini in hand (he’s a little naughty, after all). The laughs are loud, the memories run deep, and there’s no one Jake would trust more to stand by his side on the biggest day of his life.
Nico Sessa
Groomsman
Nico may be the quieter Sessa sibling, but his heart speaks louder than words ever could. A true family man through and through, he’s steady, genuine, and the kind of person who makes everyone feel cared for just by being around him. He loves a good time, knows how to celebrate, and balances his soft-spoken nature with the kind of presence you can always count on. Having him up there alongside Massimo makes Sierra’s heart full, because nothing feels more right than having both of her brothers standing proudly by her side on this day.
John Najjar
Groomsman
John is one of Jake’s longest-standing friends and the perfect counterpart to his equally amazing other half, Courtney. He’s the guy who instantly makes everyone feel welcome, brings the laughs without trying, and somehow manages to be both hilarious and genuinely kind at the same time. John is the kind of friend you can always count on, whether it’s for a quick check-in, a loud group laugh, or, most importantly, an espresso martini (he’s proudly Team Espresso with Ryan Mills). The laughs are plenty, the memories run deep, and there’s no one Jake would trust more to stand by his side on the biggest day of his life.
Dan Smith
Groomsman
Dan is a true locker room guy, loyal, solid, and always in Jake’s corner. He’s got a hilarious personality, gives the kind of hugs that can turn your whole day around, and somehow manages to balance being the funny guy and the dependable one all at once. Whether he’s coaching football, hyping up the group chat, or sending something that makes everyone cry laughing (appropriate or not), Dan is the guy you want around. He’s been part of Jake’s world for years, bringing laughter, loyalty, and a whole lot of heart, and there’s no one Jake would rather have standing beside him on this day. (Though Sierra still says he’d crush it as the driver of their wedding trolley… in pink overalls, of course.)
Theo Sarette
Groomsman
Theo is Jake’s longtime coworker, trusted confidant, and full-blown work wife. Their relationship is basically a marriage—something happens, and Jake’s first reaction is, “I have to call Teddy.” It’s giving life partner energy, just with matching uniforms. But beyond the banter and inside jokes, Theo has been a steady source of support for Jake through all things work and life. He’s thoughtful, dependable, and one of those rare friends who doesn’t need to be the loudest in the room to be one of the most important. He’s also the reason Sierra met Micayla, so if you’re wondering who to thank for this magical wedding party lineup, look no further. Jake and Sierra can’t imagine this day without him, and honestly, neither of them would want to.
James McCarthy
Groomsman
James is one of the most genuine guys you’ll ever meet, hilarious, thoughtful, and always the first to check in to make sure everyone around him is okay. He’s the kind of friend who might forget to respond to a text or change plans last minute, but his heart is so good no one ever minds (and somehow, it always just works out). Steady, loyal, and endlessly kind, James has been an important presence in Jake’s life for years, through both the everyday and the big milestones. He brings laughs, grounding energy, and that rare ability to make everyone feel comfortable just by being himself. The wedding party wouldn’t be complete without him!
Matt Ball
Groomsman
Matt is the quiet genius of the group, brilliant, humble, and soon to be a doctor (no big deal). He’s one of Jake’s longest and closest friends, the kind of steady presence who has always brought calm, wisdom, and a loyalty that doesn’t need to be loud to be felt. Through every chapter of Jake’s life, Matt has been there: dependable, thoughtful, and the friend you can always trust for perspective, encouragement, and the kind of advice that actually sticks. He’s as genuine as they come, with a heart as steady as his mind is sharp, and Jake couldn’t imagine this day, or any version of life, without him standing by his side.