Jimmy and Emma met while working at the Kittansett Club in Marion, MA. After a first date at Mirasol's Cafe, a few staff parties, and the infamous trip to Boston where Emma got food poisoning, they were hooked. The couple dated long-distance while Emma was at Wheaton College and Jimmy pursued a career as a golf professional in Florida. Then, they dated longer-distance while Emma studied abroad in Germany for 6 months. Jimmy made the trip to visit her and they explored Bavaria, and even took a trip to Paris! They both returned to Wareham in 2018 for a summer before Jimmy returned to Florida, and Emma went back to Germany for a year. Jimmy once again trekked to Germany, this time making a stop in Amsterdam for a weekend together. They planned their next chapter in Washington DC, where Jimmy landed a year-round position as a golf professional at Columbia Country Club, and Emma started her masters degree at the George Washington University. They fell in love with the city, and have lived there ever since. Jimmy even proposed to Emma at the Eleanor Roosevelt Memorial, where they visited when first scoping out DC.