The Meet Cute

In 2024, Jess and David both found themselves headed to Cancún, Mexico over Labor Day weekend — thanks to a group trip that would end up changing everything.

Jess had planned her travel with precision… until her flight from Charleston to Charlotte was suddenly cancelled the night before. Cue a last-minute dash to Charlotte to catch her connecting flight, she finally made it to Mexico. David, meanwhile, was simply proud that he booked a flight from San Francisco to Cancún, and not Cabo. 😅

They met the first night at dinner, while sharing in some jokes and light banter. Jess seemed fun, but David would later joke that she “definitely wasn’t giving single vibes.” The next day, one of David’s friends gave each of them an encouraging nudge toward the other. Jess brushed it off enjoying some drinks while floating around the pool, completely unbothered. David, however, took it as a clear green light.

From then on, he turned up the charm to 11. They played games, shared drinks, danced, and David did A LOT of talking (something Jess quickly learned he excels at). Despite the unpredictable circumstances, they both realized the other was genuinely interested in seeing where this fun adventure could lead them.

How Would They Do It?

Jess was living in Charleston, David in San Francisco — basically an entire country apart. Dating long-distance? Yeah… not exactly convenient or easy. But somehow they both knew there was something worth exploring.

A month later, David flew to Charleston for a week, and by the end of the trip, they were “official.” Jess then invited him as her date to her sister Megan’s wedding the following month.

From there, they became pros at cross-country travel. David heading East, Jess heading West, and both going places in between over the next several months, traveling so much they basically lived at the airport.

Finally in June, the grand plan came together: Jess packed up her life — including her two cats, Sadie and Leo, who were not exactly thrilled about the idea — and David helped move them West to San Francisco. They’ve all been happily settling into life under one roof ever since.

The Proposal

Things moved quickly for Jess and David — but always with intention. From the start, hard conversations were had to ensure they were on the same page. So when June rolled around and David helped move Jess to California, he took the opportunity to ask her parents for their blessing. They didn’t just say yes — they were thrilled that their daughter FINALLY found someone who loved her so much and was willing to accept the responsibility of taking care of her.

Once David had the ring, he enlisted Megan’s help to plan a Labor Day weekend proposal while the family was in Atlanta for Battle of the Birds (USC vs VT — Go Hokies 🦃!). The plan was solid… until it wasn’t. The chosen spot was suddenly swarmed by people in cosplay who were attending DragonCon, and every backup idea kept coming up short. A packed football game, crowded dinners, even the Georgia Aquarium (all while carrying the ring in his pocket during every opportunity) — the universe simply said, “Not this weekend.”

When they returned to California David had to start over. And, with a joint vacation to Japan coming up, he knew one thing for sure: he wouldn’t risk carrying the ring around on another trip, let alone an international one. So on September 9th, the night before the trip, his new plan went into motion.

Of course, it was one of those chaotic days where both of them were drowning in work, packing, and stress — they barely had the chance to speak to each other all day. As the sun began to set, David suggested they go on a walk to get some fresh air. Jess agreed, but in true Jess-fashion, made David agree that they would be productive when they got home to finish prepping for the trip. They headed out on their usual route toward the boardwalk behind Oracle Park (Go Giants ⚾️!), a spot where The Bay meets the San Francisco city skyline. There, standing by the quiet dock with San Francisco glittering behind them, David started asking Jess questions about their upcoming trip…then a few about their life together…and the final question, “Will you marry me?” as he got down on one knee. Jess says she immediately blacked out — but eventually said “Yes.”

Everything Else

After saying “yes,” David and Jess jetted off to Japan as a newly engaged couple — but apparently, jet lag is no match for wedding planning.

Between sushi, sake, and sightseeing, they somehow found themselves making notes, tossing around ideas, and plotting their dream day. Who knew bullet trains and ramen could be so inspiring?

They couldn’t be more excited to bring their family and friends together, celebrate the love they’ve found in each other, and share all the laughter, joy, and happy tears with everyone in Temecula in August 2026!