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Nick was in Chicago for the Windy City Smokeout event. Jessica was in Chicago for a friend's Bachelorette Party. The girls had just finished dinner and stopped to check out a random bar, the Boss Bar in the River North area. Nick noticed the group of girls walk into the bar and he and his buddy decided to skip waiting in line where they were and follow the girls in. The guys took a seat at the back bar, no girls in site. But! Eventually the girls made their way to the back bar and were ordering drinks next to the guys. The guys kindly bought the girls a round of shots (Pineapple Upside Down Cake shots), and also continued to buy drinks for them the entire night. Jessica approaches Nick at the bar. Starting off by ridiculing him for having a Chevy logo as the background on his phone (although she has nothing against Chevy's). As the conversation continued, Jessica's crush on Nick was growing, she got his phone number (although it was later discovered he typed in the wrong number) and they became friends on Snap Chat (which saved the day). As the night went on and it was time to leave the bar, Nick mentioned to Jessica that he'd really like to kiss her but didn't want to in front of her friends. Jessica cleverly suggested that Nick had to use the restroom... in which he was sharp enough to realize what she meant. So he walked towards the restroom and following shortly behind was Jessica skipping down the stairs to give Nick a kiss (awww).
After getting the phone number confusion figured out, Nick and Jessica chatted daily for weeks. After 3 weeks, they decided it was time to meet up again. They planned to meet on a Sunday for brunch in Indianapolis which was halfway between Nick's home in Lisle, Illinois and Jessica's home in Dayton, Ohio. On the day before their scheduled date, Nick had quite a crappy day and decided to just go to Indy a night early. He told Jessica and she just decided to go ahead and go to Indianapolis early too! They had some Mexican food for dinner and checked out the sites in Downtown Indianapolis. Continuing their date on Sunday, they had brunch at a brewery, then went to the Indianapolis Museum of Art, and also adventured around to find a cute little ice cream shop in an old railroad station. Needless to say, it was difficult for them to say goodbye and head back to their homes.
After months of back and forth trips to see each other, the decision was made that Jessica would eventually move up to Illinois to be closer to Nick. The major thing standing in her way was selling her house in Dayton. After mentioning to friends that she was looking to sell her house, some close friends mentioned that they would be interested in checking it out as they were looking to buy soon. Her friends thought the house would be great for them and this propelled the activities to get Jessica moved to Illinois (which included Nick taking several loads of boxes and also filling a racing trailer with her stuff). She put her notice in at work, closed on her house, packed up her car on the 20th of April and moved in with Nick!
Nick was strongly suggesting that he and Jessica go to Ohio for St. Patrick's Day weekend. She planned for them to stop for dinner at a seafood restaurant in Indianapolis on Friday night and then continue to Ohio to see all of her friends and her immediate family. Yet she didn't know that a proposal was going to happen. They pulled into the restaurant parking lot around 9 PM, it was a dark and chilly night. Jessica being hangry by that time of night, decided to hurriedly start walking towards the front door. Nick made an attempt to slow her down but it wasn't working. He finally says, "Will you just stop and turn around?". As Jessica turned, Nick gets down on one knee, opens a ring box which lights up to show the ring, and he asked her to marry him. Jessica was completely shocked that he was proposing at this moment since she had planned the dinner and the weekend. She walked towards Nick and just stared at the ring and asked, "Well are you going to put in on my finger?". Nick responds, "Well are you going to say yes?" and she of course said Yes! Then they had a tasty seafood dinner and were able to share their engagement the next two days with their friends and family!