September 19, 2018: First Day We Met November 11, 2018: First Kiss November 15, 2018: First “Official” Date November 30, 2018: Andrew's First Time Meeting the Olson Family December 14, 2018: Taylor's First Time in Oregon & Meeting the Meyers’ Family January 15, 2019: Andrew and Taylor Started Dating Long-Distance May 3, 2019: Andrew Picked Taylor Up From the Airport December 13, 2019: Andrew Asked Mr. Olson for His Daughter's Hand in Marriage January 3, 2020: Andrew Bought a Ring February 16, 2020: Andrew Popped the Question
If you know anything about Taylor, you know that she is almost impossible to surprise, but Andrew did it. Taylor’s 21st birthday was on February 16th so they had already planned on going on a safari wine tour in Malibu. Little did Taylor know, but Andrew and Michelle, her mom, had been in contact planning, for weeks in advance. Knowing that Andrew wanted Taylor's core people there for the immediate reaction as well as an after party, her birthday seemed the best possible option to surprise Taylor. The day came, and Andrew had hidden the ring inside his camera bag, which he had brought along so Taylor could have as many pictures as possible. Taylor, being as inquisitive as ever, was extremely curious as to why Andrew insisted on bringing the bag everywhere. Shortly after, Taylor and Michelle were wanting pictures together with Andrew as the cameraman. Andrew kept asking to have them move to different locations, where he knew the pictures of him proposing would be up to her standard, only to have Taylor say time and time again, "No. Right here is fine." Andrew finally settled on one spot and had him and Michelle switch and as soon as he stood next to Taylor and swallowed some liquid courage, got down on one knee and asked. Taylor, being caught off guard, immediately responded with a sea of tears and forgot to answer Andrew. Andrew knew this was a yes and put the ring on her finger