On a hot July day in 2020 while socially distancing, Missy and Phil matched on a dating app called Bumble. After exchanging messages for a couple of weeks, Phil finally asked Missy out for a drink. Their first date was at City Mouse (which is now permanently closed), where they were having so much fun chatting the bar kicked them out at closing. When Phil found out Missy was a golfer that pretty much sealed the deal.

Phil pulled off the nearly impossible task of surprising Missy. She had been in Lake Geneva Friday evening with some college friends and was planning to be home for a late dinner reservation Phil had made that he promptly cancelled after forwarding the email confirmation. From the minute Missy got home, she was foiling the plans Phil had put in place. She noticed the gate to the back patio was unlocked and immediately locked it when she got out of her car. Missy then went out to water the flowers and found a camera installed on the fence and came running inside to ask Phil about it and he claimed to be concerned about security (despite the alarm system they have connected to the police on every door and window in the house). Eventually Phil asked Missy to have a drink on the patio before dinner and as soon as they went outside, she noticed their front door was open (a signal to those hiding outside in the driveway) so Phil went back inside and pretended to close it. Phil proceeded to raise a toast that took Missy a good 30 seconds to realize he was proposing and then he got down on one knee and pulled out the ring box he had hidden under the fireplace table. Missy of course said yes! Phil arranged for Missy's parents to come back to Chicago (they had just been visiting the prior weekend) and after proposing suggested to call them. Missy wanted to enjoy the moment together for a few minutes until Phil decided they couldn't wait any longer. When Missy Facetimed her Mom, she was holding the camera suspiciously close to her face and Missy realized they were in the driveway and both Phil and Missy's parents, siblings and best friends/neighbors were waiting to surprise them to celebrate. It was a fantastic evening and more friends came over to celebrate later that evening making for a night Phil and Missy will never forget.