Back in 2001, Mike Lupo and Tom Slimak were colleagues at Progressive. The Slimak's and the Lupo's were good family friends who had always joked about Will and Alex dating when they were older. Fast forward to 2018, and Alex is going over to Will's dad's house for instructions on how to dog sit while they are on vacation. Will is at a friend's house. While standing in the kitchen with Alex, Tom calls Will and says "I'm here with your future girlfriend, Alex Lupo." Will says (while on speaker phone) "no thanks" yet immediately speeds home. When Will arrived home, they had seen each other for the first time since they were about 7. Alex couldn't get over the fact that she was unreasonably rejected and Will couldn't stop thinking about Alex. The next morning, Will had left for vacation and Alex went over to feed the dogs. Alex opens the dog food container and sees a note that reads "Add me on snapchat @willslimak." Will spent his entire vacation talking on FaceTime with Alex for hours on end. They had their first date the day after Will got back. Five and a half years later on Christmas Day, 2023, Will and Alex got engaged in Mexico and are now planning a June 2025 wedding.