Connor and Siobhan met at a picnic table at The Playwright in South Boston in 2020 on a triple date set-up by Siobhan's cousin, Sophie. After a successful first date, Siobhan asked Connor for his number, but due to Connor's tuna-fishing schedule, Siobhan had to wait several weeks for a second date. Siobhan and Connor spent the following years getting to know each other. Connor taught Siobhan how to ski and Siobhan showed Connor what a Cape Cod summer is all about. In October 2023, Connor proposed at the Boston Harbor Hotel, during a rainstorm...a true Irish engagement.