On an early December day, Andrew and Jenna were idly passing their time swiping through Tinder, with no clue what it was about to lead them to find. Initially, Jenna swiped right as she found his tagline funny. It said: "I am actually a 55-year-old woman named Gertrude trying to catfish you". When Andrew saw her profile with her glowing smile in each picture, he decided to swipe right, and to his delight, the "It's a Match" message appeared. To begin their conversation, he congratulated her on being his 100th match, and she asked what prize she won for it, expecting some perverted retort. He caught her off guard when his response was PG and more philosophical. They continuously chatted for the next 2 weeks and decided to meet in person on 12/21/14. They took a late afternoon/early evening walk around Moore Mesa, where they traded stories and talked about life and their families. Although Andrew can be reserved, he had no problem conversing with Jenna. They went their separate ways for winter break but continued texting and sending photos from Jenna's trip back home to Sacramento and Andrew's trip to New York. On the night of January 3rd, 2015, Jenna returned to UCSB, and she and Andrew decided to go on a moonlit walk at Ellwood Beach. They now consider that date their anniversary. There they shared their first kiss, and since then they have been inseparable.

Andrew planned for months on end on how to propose to Jenna. He knew he wanted it to be in Hawaii when they were there with her family to celebrate Jenna's parents 25th wedding anniversary. So, he decided he was going to make an app that depicted the story of their relationship. The app would have a series of photos that told the "story of us". One night in Hawaii, Andrew took Jenna for a moonlit walk along the beach, much like their second date. He showed Jenna the "Story of Us" app and she scrolled through, happily reading their story. Towards the end of the story, he used pictures of Jenna and her family to help ask this important question. First showed a picture of Andrew, Jenna, and her parents, who were discretely holding a small sign with the word "Jenna". Next was a picture of Katie (Jenna's sister), Andrew, and Jenna, where Katie was slyly holding up the word "Will". Then came a picture of Steven (Jenna's brother) , Andrew, and Jenna, in which Steven was holding the word "You". That was followed by a picture of Jenna holding a Trailblazers sign but Andrew had photo shopped the sign to say "Marry". Lastly, Jenna looked down and Andrew was on his knee holding a box that said "Me" and inside of it was a beautiful ring. Jenna smiled and said, "Yes!" so quickly that she is not sure if he actually said it out loud first.