Katelyn + Ryan

October 12, 2024 • Boston, MA

Katelyn + Ryan

October 12, 2024 • Boston, MA

How it Started

It all started in March 2021 when Ryan correctly answered Katelyn's hinge prompt "I bet you can't guess what sport I played in college". Slightly impressed that a handsome guy actually got it right (Lacrosse and ambitious enough to ask if she played midfield or attack), Katelyn replied and the conversation progressed. After the small talk dwindled, Ryan asked Katelyn to meet in person and... silence...


Katelyn's busy life got in the way of Hinge and she didn't answer for days until Ryan sent her another message saying something along the lines of "its okay, I understand if you're nervous." Now on the defense, Katelyn replied saying she wasn't nervous (she secretly was extremely nervous) and ultimately agreed to meet up with Ryan.

The First Date

Ryan suggested they meet up halfway at Game On by Fenway Park at 8:30pm on a Tuesday (way past their bedtimes for a week night!) Katelyn agreed and in true fashion showed up 30 minutes early because she was afraid of being late due to the unknown city parking situation. To calm the nerves (and kill time), she FaceTimed Matron of Honor Abbie. At one point Katelyn said I think I am just going to go back home and cancel, I dont want to go in. Shoutout Abbie, and Nick, for being stern with Katelyn and pretty much forcing her to go in.


8:30pm finally rolls around and Ryan and Katelyn both stroll into Game On and get a seat at the bar. Somehow they were the only ones in the whole place! When the waiter asked their drink order, and they both simultaneously ordered a Blue Moon with an orange please. Green Flag #1! The conversation never stopped. They talked about sports, travel stories, work and many other topics until the restaurant was closing. Green Flag #2! Lastly, Ryan walked Katelyn to her car to make sure she was safe AND texted her to ensure she got home. Green Flag #3! Lets say they both knew that wouldnt be the last they would see each other!


Ryans favorite line nowadays is I rented out Game On for our first date! because the whole place was empty.

Their time in Boston

As time passed since their first date, Katelyn and Ryan spent more and more time together, turning their meetups into a daily occurance. So many memories were made in Boston, where Katelyn grew up. Long walks through the city, past the Boston Harbor Hotel, their frequent visits to the seaport, runs around the charles river, going out with friends and everything in between, their time is Boston is something they will always cherish!

Katelyn and Ryan are so excited to welcome everyone to one of their favorite cities to celebrate their marriage!

The Proposal

What an adventure this was for Ryan and family! With zero pressure from Katelyn, of course ;)


Each year, the Keeney Family visits one of their favorite places - Maui, Hawaii. In 2023, Katelyn was finally going to get to experience Maui, with the Keeneys! The trip had been planned for months, with Ryan secretly planning the big proposal to be during their trip. Sadly, Maui was struck by wildfires that ended up canceling their vacation.


In comes the change to go to the Keeney family house in Coronado, California. A beautiful place that never disappoints and Ryans hometown. Katelyn and Ryan arrived Saturday and there were loose plans for each day. Every day except for Wednesday, September 20th, the day we were celebrating Ryans 30th Birthday as a surprise that had occured a week prior. Susie and Carly were including Katelyn on all the plans and even had Katelyn send 30th birthday decorations for the surprise party!


The plan was to get Ryan out of the house by going to Happy Hour at Bluewater Grill on the island so the neighbors could decorate while we were out.


Unknown to Katelyn this is when the real proposal plan took over! The five on vacation together sat down, ordered drinks and apps and the manager of the restaurant, who Ryan went to high school with, walked over to say hi. Mike and Susie requested to see the view on the roof, but she said only two people can go up a time, so Mike and Susie went on up to the roof.
Little did Katelyn know, they went up to make sure the photographer was in the right spot on the sidewalk and executed a test run. The Keeneys came back down and then Katelyn and Ryan went up. Once on the roof, with Ryans heart racing, they took pictures on the bay side of the restaurant, then went around to the other side with the Hotel Del Coronado in the background, and Ryan knew it was GO TIME! They took a few pictures and all of a sudden Ryan was down on one knee asking Katelyn to marry him. She said yes!!


Moments later, there was cheering from the sidewalk. Katelyns whole family had flown in from the East Coast to celebrate and witness the moment! Tears were flowing and the celebration of Katelyn and Ryans future as one began.


We had dinner, went back to the house and not only were the 30th birthday decorations Katelyn bought hanging up, but the house was beautifully decorated for Katelyn and Ryans engagement. A great night commenced!