At the classiest bar establishment in Lincoln Park, Glascott's, Molly went for a Friday night out with her coworkers (who happened to include Ryan's brother and sister in law) under the premise of a charity event for Ryan's alma mater the University of Dayton. Little did she know that after she and Ryan had locked eyes on each other and toasted to shots of fireball, the rest would be history. After chatting the night away over drinks, the couple had decided to exchange numbers. The night ended with Ryan buying Molly tacos from her favorite late night spot and winning her heart.

After a few months of planning, Ryan and Molly had been eager to jet set off to their Italian vacation this past summer. Although the excitement turned into a bit of uncertainty when they hit some bumps in their travel plans. After a nearly missed flight and delayed baggage, the couple chose to make the most of their first day in Rome by doing some sight seeing around the city. It was while Molly had been admiring the view of the iconic Trevi Fountain that she turned around and saw Ryan down on one knee! It was a picture perfect moment with a tear filled "yes" and cheers to be heard from the crowd surrounding the scene. They were able to continue the celebrations throughout the rest of their trip (thankfully with their luggage in hand) and enjoy the remainder of their adventure engaged!