Tyler and Jesse met on OKCupid, after Jesse spent an hour trying to come up with a space-themed pun to try to impress Tyler, but ended up asking about aliens instead. Two days later, they had their first date together at a sports bar to watch the Stanley Cup final. Over the next 3 hours, Tyler explained (probably too much about) the hockey game while Jesse dutifully listened and asked questions, and together they bonded over their shared interests in traveling, music, books, and love of Excel spreadsheets. Their next date was planned almost right away!

Jesse and Tyler had talked many times about the future and both knew that they wanted to always experience it together. Jesse surprised Tyler with dinner at home from the same restaurant as one of their first dates, and told Tyler of all the places where he had further fallen in love with her. At the end of this list, in their shared home together where they learned to love each other more every day with the little things in life, Jesse proposed to Tyler. She said she would be the happiest person of all time.