THE MATRONS
Regan Barron
The friendship between Regan and Sydney started with a literal "bang" when Sydney accidentally threw her entire lunch tray in the trash in 6th grade. Things only escalated from there, including getting kicked out of Ms. Pepper’s class for a giggling fit that just wouldn't quit. They’ve since taken that laughter worldwide—shopping and eating their way through Austria and France, and sipping wine in Bordeaux and Provence. Whether they’re tearing up the streets of NYC or the slopes of Vail, the party never ends when these two get together.
Known For: A laugh so contagious it’s a liability in a classroom setting.
Met Sydney: 6th-grade lunch (RIP to that lunch tray).
Wild West Superpower: Being able to find the best shopping and the best wine in any zip code.
Favorite Western Spirit: A crisp glass of Sancerre—or whatever is being served at the Big Sky saloon.
Ashton McFarlane
Ashton and Sydney hit the ground running at their very first day of cheer camp and haven’t slowed down since. From trading cheers for motorcycle rides with their dads to hosting a legendary (and very "Hollywood") joint 13th birthday party, they’ve been a two-woman posse through college and beyond. Whether they are bonding over Dona’s famous tuna and cheesy hot dogs or hunting for the perfect margarita, Ashton has been a constant in the adventure. As a Matron of Honor, she’s bringing that lifelong loyalty from the East Coast to the Big Sky.
Known For: Co-starring in the "Hollywood" 13th birthday bash of the century.
Met Sydney: Day one of cheer camp (stunting since the start).
Wild West Superpower: Being able to transition from motorcycle rides to mountain-chic glamour effortlessly.
Favorite Western Spirit: A margarita (extra salt, please!).
Anna Chapman
Anna and Sydney’s bond started with cheer mats and Care Bears, but it quickly expanded across the globe. From childhood sleepovers to navigating the streets of Sicily during their study abroad, they’ve been through it all. Whether they’re exploring a new country, sharing a quiet cup of tea, or having a deep heart-to-heart over a cocktail (or mocktail!), Anna has been Sydney’s go-to confidante for years. Having walked the hills of Sicily together, it’s only fitting she’s by Sydney’s side as they celebrate a Sicilian-inspired proposal under the Big Sky.
Known For: Being the best travel partner through multiple time zones and countries.
Met Sydney: The cheer days (back when life was all about Care Bears and sleepovers).
Wild West Superpower: Navigating any terrain and planning the perfect trip
Favorite Western Spirit: A high-end gin cocktail or matcha (depending on the day).
Lucy Laird
From the moment Sydney knocked on Lucy’s door the summer before fourth grade, a lifelong partnership was born. They’ve survived everything the "Wild West" of childhood could throw at them—from neighborhood adventures and cheerleading stunts to sorority formal dances. Despite the miles between them (including those unforgettable Maui visits to see Lucy and her boys!), they haven't missed a beat. Lucy has seen Sydney through every chapter, and there’s no one better to marry Sydney and Jason.
Known For: Being the "new neighbor" who became a forever sister.
Met Sydney: Summer before 4th grade (a literal door-to-door recruitment).
Wild West Superpower:Surviving cheer camp and sorority life with her sanity intact.
Favorite Western Spirit: Something fresh with fruit like the island of Maui
THE BEST MEN
Jon Drew
Jon and Jason’s partnership started in 6th grade, fueled by airsoft battles and potato cannons in Ohio. They took their talents to Purdue, where they were founding members of the "Jam Boyz" and dominated on the lacrosse field. At 25, they pulled a true "outlaw" move: they quit their steady jobs and headed west to Colorado to start their own construction company. After 26 years, 3 states, and 23 years of living in the same zip code, Jon is the brother Jason chose to build a life—and a business—alongside.
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Known For: Quitting the 9-to-5 to chase the Colorado dream and starting a construction empire from scratch.
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Met Jason: 6th grade in Cleveland (post-New Jersey move).
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Wild West Superpower: Can build a house—or a potato cannon—in record time.
Favorite Western Spirit: A Purdue "Boilermaker" or a celebratory Colorado craft beer.
Tyler Saunders
Tyler and Jason have been a two-man posse since day one. From sharing a room in New Jersey to navigating the move back to Cleveland, they were so tight they famously turned down the neighborhood kids' offer to play because they "were good" just hanging out together. They ran trails together in cross country (where Tyler almost stole Jason's varsity spot) and have remained close despite living half a country apart. He’s the brother who has been in the same "bunkhouse" since the beginning.
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Known For: Being the only brother in history to never get into a fight with his sibling.
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Met Jason: Literally at birth.
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Wild West Superpower: Long-distance endurance (from cross country trails to keeping a bond strong across state lines).
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Favorite Western Spirit: Whatever is being served when the Cleveland brothers finally reunite.
Mike Saunders
Despite a nine-year age gap, Mike was never just the "little brother"—he was a full-fledged member of the crew, often seen being towed behind Jason and Tyler in a Radio Flyer wagon. Mike famously refused "playdates" with kids his own age because he only wanted to hang out with the big guys. From spending college spring breaks in Denver to enduring the perpetual heartbreak of being a Cleveland Browns fan, Mike has always stayed loyal to the brand. He may have gone to the "wrong" school (Indiana!), but he’s the first one Jason wants by his side in Big Sky.
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Known For: Trading beach spring breaks for mountain trips and refusing to hang out with "babies" since 1996.
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Met Jason: Since birth
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Wild West Superpower: The "Browns Fan Resilience"—able to handle any disappointment with grace and a sense of humor.
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Favorite Western Spirit: A cold drink to settle the Purdue vs. IU sports banter.