The Story
This may come as a surprise in a world full of dating apps, but Brett and Ash met in real life. They were both at the Sundance Film Festival in January 2018 doing “work stuff” (We put work stuff in quotes because anyone who knows Sundance also knows that half of the “work” is having fun.)
Unbeknownst to them, they had a mutual friend in Ashley’s co-worker at Snapchat, Ryan Gordon. Ryan, Ashley and a group of their colleagues were all at the No Name Saloon Park City for happy hour, when Ryan told Brett to stop by and meet them. Never turning down a good time, Brett showed up.
When they ended up on opposing teams, standing side by side, Brett immediately noticed Ashley, but didn’t make the best first impression as Ashley trounced him in multiple shuffleboard games. Or, so he thought. “I was immediately drawn to how funny Brett was during that game of shuffleboard,” says Ashley. “I kept winning and winning, and his reactions were so over the top, mostly just to get a laugh out of me.”
Later that night, the two met up again, so Brett could get Ashley’s Snapchat colleagues into a party at TAO Sundance. (Now, Brett usually gets around five names on the guestlist, but the Snapchatters always show up with way more people than they say they will – and Brett was eager to impress Ashley after the shuffleboard disaster – so he managed to get 25 guests inside.)
While at the TAO party, Brett made his way to Ashley. Assisted by a few vodka sodas, he worked up the courage to get her number, and asked if they could hang out back to LA. Ashley didn’t really give Brett a firm answer on that, but he knew he would keep trying.
Back in LA the following week, Brett asked Ashley out on their first date to Soho House West Hollywood.
While it took just that one first date for both to know that there was something special between them, there was never just one moment where Brett knew Ash was the one. “Our relationship progressed in such an easy and natural way, that each time we took the next step in our relationship, it was like it had always been that way,” he says. Adds Ashley: “The sense of humor we share and just how much fun we can have together in any situation is one of the things I love most about our relationship. I know that Brett always wants to make me smile.”
The engagement
Brett’s Instagram caption of Brett and Ashley’s engagement perfectly sums up the proposal: “You knew this was coming!!!” Ironically, everyone knew it was coming except for Ashley.
Under the pretense that this was just an effort to uphold Ashley’s long-standing tradition of traveling on her birthday, they had set off for a long weekend getaway to Big Sur. One thrilling two-seater plane ride via a single engine Cessna later, Brett and Ash landed at the Monterey airport.
“We just need to make one quick stop at Fedex in Monterey, to pick up your last-minute birthday gift,” Brett told Ashley. (By this point in the relationship, Brett knew that the Jackson family does not mess around when it comes to birthday gifts – Jackson family gift ceremonies can last up to an hour – so to Ashley this was a perfectly reasonable detour.).
On Day Two of their trip, Ashley and Brett found themselves on a gorgeous seaside hike, that Ashley had planned for them (Smart tactic, Brett?). Highly distracted by the majestic beauty of Big Sur, Ashley completely failed to notice Brett’s increasing nervousness and insistence on finding a lookout point with no other people around.
Unsatisfied with the lack of privacy, Brett guided Ashley inland on the trail, where they stumbled upon a stream that led out to the ocean. With nothing but the sound of the water behind them, and the shade of the forest shielding them from the summer sun, Brett turned to Ashley and uttered this now infamous quote: “Soooo, guess what?” as he pulled a ring out of his pocket and proposed. Ashley couldn’t stop laughing and smiling as she finally understood the ruse. Brett had to clarify that she indeed said “Yes!”
A passersby was quickly flagged down to snap a photo that immortalized the moment (“Hi! We JUST got engaged!”), after which a celebration ensued at the Big Sur Bakery for a good ol’ pizza party. Brett and Ash spent the rest of the weekend popping champagne and basking in their excitement and the congratulatory texts and phone calls from friends and family. Big Sur will no doubt always hold a special place in their hearts!
