Darren and Tess met at Housatonic Valley Regional High School were Tess was the Girls Varsity Soccer Coach and Darren was hired as the new Athletic Trainer while he is in his off season working for the Washington Nationals MILB. Darren and Tess started dating in February 2015. Darren proposed in December 2016 at Equinox Resort in Vermont on a weekend get away. Tess's parents use to vacation to Sandyport Beach Resort in Nassau, Bahamas for many years, which is the reason for Darren and Tess having their destination wedding at Sandyport. They have recently purchased a home nestled in Southern Berkshire Country close to Tess's family.