Geography: Brian UMass Amherst, Jen Colgate July 2013: First photograph of Brian and Jen together, sticking their tongues out on Nick’s 21st birthday. Spring 2014: Jen Visits UMass. April 2017: “Hardcore flirting in the corner of a bar”- Our friend Lisa. March 2018: St. Patrick’s Day in Southie before Brian shipped off for the Secret Service academy. Brian and Jen share whiskey. Jen shows Brian her sister Kristin's hidden engagement ring. May 2018: Brian starts with the Secret Service. Geographically: Brian in Brooklyn and Jen in Boston September 2020: Jen moves to Poughkeepsie as part of PA school. October 2020: Brian and Jen message all Halloween about life. June 2021: Single Brian drunk texts Jen while she is at her sister Kari’s bridal shower. October 15, 2021: Brian confesses his long-harbored feelings for Jen at Nick and Kari’s wedding. November 17, 2021: Double date dinner with Nick and Kari, Jen now single! Brian did not know. November 20, 2021: The NYC night that changed everything! Brian tries using chopsticks. Jen and Brian karaoke duet to “Start of Something New”. November 27, 2021: First date at Mother Anna’s in Pembroke, MA. Brian is still in Brooklyn and Jen in Poughkeepsie. February 12, 2022: Officially Boyfriend and Girlfriend! March 2022: Jen goes to St. Thomas for school, Brian tags along. Box Bar and snorkeling fun! May 2022: Jen graduates PA school! June 2022: Jen moves to Marshfield, MA. Gets new job with Dana Farber. July 2022: Group trip to Cancun, Brian fake proposes one night… November 2022: Brian passes CAT school! Geographically: Brian in Virginia, Jen in Massachusetts. October 10, 2023: Brian and Jen hike Machu Picchu. Brian proposes for real. They get engaged!