Chengsu and Will met for their first date at a restaurant called Surisan after having it planned for two weeks due to schedule conflicts (very common in the Bay area dating scene). They walked along North Beach and continued sharing their stories at Maritime Wine, where they were the first two customers at the wine bar. Neither of them wanted the date to end and Chengsu insisted on meeting Will's dog, Chief. The two spontaneously bought movie tickets before Chengsu caught an Uber back home, and the rest was history.

Will had surprised Chengsu with a trip to Hawaii in September for her birthday in March. She had never been to Hawaii before, but she had plenty of time to prepare for the trip in 6 months. Within the 6 months, Will had accepted a job based in Los Angeles starting in October, which meant a long distanced relationship for the foreseeable future. The evening after arriving in Maui, and before their dinner reservation, Will decided to stop by a secluded beach at the Ritz Carlton hotel to take photos during the sunset. With no on else on the beach, Will prepared his camera and distracted Chengsu before proposing (you can ask Chengsu about the distraction, it may or may not have involved a whale).