Dylan and Libby are both from Crandon, WI. Although Dylan was a year older in school. It’s Crandon; everybody knows everybody. Dylan used his 14 yr old charm to pursue Libby via Yahoo Messenger (dial up internet days ugh). They exchanged phone numbers, stayed up late at night talking on the phone. And the rest is history. They dated all throughout high school, did long distance for a year while Dylan headed off to UW Madison, until Libby came down the next year. Cue present day!
Dylan and Libby headed to Chicago for a weekend getaway to include shopping and eating (or so she thought). Dylan surprised her by making dinner plans on the Odyssey- a dinner cruise on Lake Michigan. At this point, she still didn't necessarily think anything was up (after that many years together, you do this kind of stuff sometimes). After dinner, the waitress insisted that they go up to the Captain's deck to look at the view and take some pictures. Upon entering, it was filled with candles and rose pedals (this is when she thought something might be going on). Staff asked if they would like a picture with the skyline view in the background, and during the picture Dylan got down on one knee and asked Libby to marry him! The night ended with a fireworks show and two bottles of champagne!