Jenna and Jesse both work in higher education and regularly attend college fairs and professional conferences. They initially met at the Boston Latin School College Fair in 2015 and ended up sitting at adjacent tables at Sweet Cheeks Q for dinner that night. Several years later, Jenna and Jesse attended the NACAC/NEACAC Super Conference in Poughkeepsie, NY where Jenna was living and working at the time. In a very crowded gymnasium, Jenna immediately saw Jesse and re-introduced herself. They continued to run into each other throughout the conference and eventually matched on Tinder. Jesse invited Jenna to go on a hike the next day and the rest is history!

Every year, Jenna and Jesse take a Chrismukkah (holiday) photo. They bought a little tree and decorated it with fun ornaments and fake presents. They set up a tripod and put Jenna's phone camera on a timer. After taking close to 30 photos, they still wanted to take at least one more. As the timer was about to go off, Jesse reached behind the tree and pulled out a ring box. The camera captured the moment perfectly and of course, Jenna said yes!