Dennis and Jen met in the most millennially traditional of fashions: on a dating app called Bumble, bonding over the appropriate use of the Oxford comma (he's anti, she's pro). They decided to set up their first date at a sushi restaurant halfway in between them. On the day of their first date, Jen ended up having a difficult decision to make: meet Dennis for the dinner or attend the birth of her good friend Deanna's first child. For better or worse, she chose the former...and showed up "4 hours late" according to Dennis (ahem, it was only 15 minutes). At least there were no false appearances... (and she went to the hospital afterwards to meet the baby!)

In August 2018 Dennis and Jen made plans to stay at Disney's Grand California Hotel for a brief one-night getaway over Labor Day weekend. After working a sleepless Saturday-Sunday 24-hour shift and attending an all-day baby shower on Sunday, Jen finally showed up at the hotel to find Dennis particularly excited about their adventures in store for them ahead. After watching the fireworks and going on a couple rides Sunday night (and eating several churros), Jen was finally allowed get her first sleep in roughly 36 hours. The next morning, Labor Day (September 3), like an eager 8-year-old, Dennis rousted the still sleep-deprived Jen out of bed at 6:30 AM to take part in "Magic Hour" at Disney's California Adventure (a benefit where hotel guests are allowed to enter the park 1 hour early). After an hour of racing around DCA, including being the first guests on Cars Radiator Springs Racers and riding Toy Story Mania (Jen’s favorite ride) 3 times, Dennis suggested they go over to Disneyland for a breakfast macaron and coffee. Upon entering Disneyland, Dennis started dragging Jen in a direction away from her beloved macarons, which did not sit well with her. Feeling harried and "hangry," Jen resisted but nonetheless relented to Dennis’ misdirection. Upon reaching a particular spot at the top of Main Street, Dennis asked Jen “[d]o you know where we are?” to which Jen curtly responded, “yeah, we're at Disneyland ” (she had a few other choice words in her head, feeling like the question was superfluous). Dennis then reminded Jen that they were standing in the exact spot where Jen had taken Dennis 435 days before to watch the Main Street Electrical Parade for his birthday, the day Dennis first thought that Jen was "The One." Dennis then got down on one knee and asked Jen to marry him, and the rest was history.