Will and Taylor both attended Newbury College. They had classes together here and there but rarely spoke. Will graduated in 2012 and went along with his life, while Taylor was still in college and graduated in 2014.

While Will was in college, he played soccer. Taylor's friend had a boyfriend who was also on the soccer team and friends with Will. In 2018, Taylor's friend and Will's friend from soccer got married. At their wedding, Taylor and Will connected and started dating a few months later.

Fast forward to 2022, about 8 days before Taylor's 30th birthday. Will tells Taylor they are going to meet someone in Boston for dinner. She agrees to go and doesn't think anything of it.

They drive into Boston, park in a parking garage, and Will says they have to walk a little bit to the restaurant. They walk to Rowes Wharf where there's a big archway and usually an American flag hanging, but there was no American flag that day. They walk towards the center and Will tells Taylor to stop. Will gets on one knee and says "I'm gonna ask you a question but you have to say yes" and displays a beautiful ring. Taylor says "Yes!", they kiss and hug and Will tells Taylor that there are family and friends in the corner that were able to watch the whole proposal.