Jess and Bennett met in August 2016 during analyst training for their first jobs out of college. Bennett, the experienced former summer intern, was already staffed on a project and that impressed Jess. Bennett immediately noticed her confidence and how she wasn’t afraid to speak up or ask questions. However, Bennett was based in Boston, and Jess in San Francisco, so there were few opportunities to interact.
Fast forward to February 2017, they got staffed on the same project which was no coincidence, and became fast friends. Their professional relationship grew over coffee runs, whiteboard brainstorms, 1:1s and late nights at the office creating PowerPoint slides. Jess loved hearing about Bennett’s three sisters, Dartmouth days, and nerdy, yet endearing, sci-fi book obsession. Bennett was drawn to Jess’s warmth, and enjoyed learning about her competitive skiing glory days, upbringing in Telluride, and sorority life at Cornell.
Two months and many tequila shots later, they bonded over a mutual love for games. From bowling to skeeball and giant connect four, they found each other’s competitive sides, but also quickly realized there was more than just a work connection. A week later, Bennett asked Jess on a proper date to Oak bar for drinks. The conversation flowed easily and was surprisingly deep. Near midnight, Jess asked Bennett if he wanted to go to SoulCycle with her at 7am the next morning. Exclaiming ‘I love SoulCycle!’, Bennett committed, excited to see Jess again yet worried because he had never actually been on a spin bike. But Bennett showed up on time and with a smile, and Jess was impressed that he made the effort.
They kept their relationship hidden from coworkers and most of the public for 9 months, though in that time they managed to fall in love, travel to the Amalfi Coast, Croatia and Rome, and meet each other’s close and extended families. In November 2017, Bennett told Keystone he was planning to move to San Francisco for Jess, and that he hoped to keep his job. In February 2018, the long distance late-night FaceTimes had finally come to an end.
The couple fell into a great rhythm in San Francisco, finding new mutual hobbies like rock climbing and tennis, exploring nearby towns like Napa, Tahoe and Big Sur, and acquiring two precious Siberian cats, Ajax and Ivy. Jess and Bennett have both since left the consulting world in favor of tech startups, but will always be thankful that work brought them together.
Bennett knew he wanted to marry Jess after enduring a very challenging year together during Covid. The support, enthusiasm and motivation Jess brought to Bennett’s life made him optimistic about the future. Jess knew early in the relationship that Bennett was the one she wanted to build her life with, maybe it was his well-rounded Minnesota values, his easy going attitude, or his kind, gentle heart.
Bennett proposed in February 2021 in Telluride, Colorado, surrounded by Jess’s family. While most of the details were a secret to Jess, Bennett did draw suspicion the day-of when he had her mom suggest a nice dress for dinner and he asked if she had her nails done. A day later, they got off the gondola in Telluride and came across another surprise, Bennett had a custom ski run sign made, saying “Marry Me Jessica” that happened to be in the exact spot where they will get married next fall, on September 24, 2022.
