The couple met through their mutual friend at a soccer game for the rec league she and Nick play for. She had been telling them about each other for months, and thought they would make a cute couple. The second time Olivia came to watch their game (because she had forgotten to introduce them to each other the first time), the two were introduced and started to chat, resulting in Olivia suddenly having an interest in soccer ;) After about a month of soccer game sideline chats and sitting by each other at church, Nick asked to take Olivia out on a date sometime. And well, we see how that went.
The day after asking Olivia out, the two went to Lakefront Park in Hobart, which happens to be across from the wedding venue! They walked and talked for hours, (throughout which Nick tried to not-so-subtly hold Olivia’s hand, and Olivia kept dodging his attempts because she was too nervous), and ended the night having dinner at Tavern on the Lake.
After a nice breakfast at Olivia’s favorite restaurant on the morning of their 7 month anniversary, Nick, Olivia, Nick’s sister Mel, and their friend Liz headed out to hike at the Indiana Dunes…or so was the cover story. They started to head up a small hill (the same hill Nick and Olivia watched the sunset from the day Nick told Olivia he loved her) with Olivia in the lead, and upon reaching the top, she turned around to see Nick on one knee with a big shiny ring in hand, and asked her to marry him. Obviously, she said yes!