SHORT EDITION: Andrew went on a blind date with a friend of a friend's coworker's little sister, Maddie! LONG EDITION: Two parallel lives were being lived in Boston. One in South Boston. The other in the North End. One was enjoying the espresso martinis at The Broadway a little too frequently. The other was enjoying enough pasta that even James Gandolfini would tell him to pump the breaks. Well, their two paths crossed because of a wedding in West Palm Beach, FL and a few degrees of separation. While Andrew and his friends were attending a wedding down in Florida in March 2018, a college friend of his friends, who also happened to be Maddie's eldest sister's coworker in NYC (bear with us), Jen, also happened to be vacationing nearby. With the help of a pool party and some painfully good-looking snapchat stories, Jen recognized that the boys were in town and invited them all to meet up. After being introduced to Andrew by their mutual friends and learning that he was riding solo up in Boston, Jen recalled that the one girl she knew in Boston (who also happened to be single) was her coworker's little sister, Maddie! She got Maddie's number from Chelsey and told Andrew that he would be crazy not to reach out. Andrew played it super cool and waited a few weeks to reach out (oops). Maddie, being easily plied with some tasty sushi, forgave him for his tardiness and the rest is history!