Catherine and Matty go way back, meeting at Holten Richmond Middle School in 2007!

From the young age of 11 to the time they graduated Danvers High School in 2014, they were always friendly and thought highly of each other.

Fast forward 5 years to when things got interesting! After not hearing from or seeing each other following high school graduation, the silence was broken with a simple Instagram Direct Message from Matty to Catherine: ‘how do I get a ticket to the reunion?’ Catherine thought to herself, ‘wow Matty Flynn? Doesn’t he have a million people he could’ve asked other than me?’

On December 27, 2019, the infamous five-year DHS class of 2014 reunion was a night to remember. Many friends can attest, the two didn’t leave each other’s side all night.

In January 2020, Catherine and Matty went on their first official date to Lolita in Back Bay for a margarita (or three). Since then, they have never looked back <3

The COVID-19 pandemic is highly relevant to the beginning of their relationship. Those first few months consisted of lots of movie nights, game nights, wine nights, and pool days where they got to know each other rather quickly. While it was a scary and unpredictable time, Matty managed to make it really fun and memorable, as he always does.

As the world slowly got back to a new normal, Catherine and Matty had a chance to integrate into each other’s lives. Catherine got to know and love Matty’s friends from URI, and they welcomed her with open arms as she attended many fun nights out with them in Southie. Meanwhile, Matty got to spend lots of time with Catherine’s Holy Cross friends, including wine nights with her roommates and several ski trips with the crew. One of the most beautiful things about their journey was getting a chance to re-bond with old friends from Danvers. Both having long-lasting friendships from childhood, Catherine got to reconnect with Matty’s “crew” and he with hers. They are very grateful that they all get to be a part of each other’s lives forever.

As far as families go, Matty fit right in with Catherine’s family (besides needing to put in a little work at the driving range). They have gained two adorable nephews and one beautiful niece during their relationship who are so special to them and have brought them many fun memories and family trips.

Meanwhile, Matty’s family welcomed Catherine and made her feel like part of it from Day 1. From backyard games in Cambridge to summer days at Long Beach, it has been nothing but fun and love uniting the two families.

On July 13th, 2024, what Catherine thought to be a normal, hot summer Saturday turned into one of the best days of her life. Matty got down on one knee and popped the question at one of their favorite places to walk – Fresh Pond in Cambridge. Two amazing friends were behind the scenes capturing the moment and popping Champagne. The proposal was followed by an epic surprise party filled with family and friends, which turned into an all night affair in Boston. It was a meaningful celebration Catherine and Matty will always cherish.

The couple is so grateful to their families who are beyond excited for the wedding and making it all come to life, especially the moms…. For Joan, her one baby girl is getting married, and for Kelly, her one baby boy is getting married, and the love and excitement is certainly felt from them.

The countdown to 9/20/2025 is on...don't forget your dancin' shoes!

Things to Do coming soon!