It all starts with Caitlin and Ryan's first date in downtown Chicago back in late January, 2016. They decided to be tourists for the evening at the Bean in Millennium Park. While watching the ice skaters and grabbing Starbucks to warm up, they quickly learned about all of each other's favorite things. After their date, Caitlin spent the entire walk back to her dorm calling her sister Bridget to share how amazing this super cute and tall guy named Ryan was.

After another couple dates, as well as day in and day out constant texting, Caitlin invited Ryan over for a pre-Valentines dinner. When the delivery driver dropped off their food in the lobby, he told Ryan and "his girlfriend" to have a good night. When heading back upstairs, Ryan looked at Caitlin and said, "I like the sound of that," and asked her to officially be his girlfriend.

Over the course of the next 7 years, Ryan and Caitlin continued to grow in their relationship and with their families. Caitlin joined many events in Delavan with the Roycroft's and even got initiated at a 4th of July party by being thrown into the pool. Ryan quickly became Uncle Ryno to their 4 nieces and nephews and been a victim of many moonings from the Boyle sisters. They both started their careers in central Illinois, bought their first home with Daisy Doggy, and try to spend as much time possible with their friends from home and school.

Come August 6th, 2022, Ryan let Caitlin know that they had plans to go visit the Chicago Botanical Gardens and then later were going to get dinner with their friends Daryl and Kayla to celebrate their upcoming wedding. Ryan had already been up north due to work training, so when Caitlin was packing for the weekend, he called her and reminded her multiple times to make sure she packed something nice to wear for the gardens and dinner. Caitlin began to grow slightly suspicious on this and immediately called her mom, Laurie, and sister, Bridget, questioning if Ryan was planning to propose. After both telling her no way, Caitlin agreed and thought nothing of it moving forward.

As Caitlin and Ryan were walking into the Gardens that afternoon, Ryan pulled Caitlin aside towards a larger pond and asked her what she thought about the sculpture in the middle. Caitlin was very confused and turned to look at it, when turning back to respond to Ryan, Caitlin saw him down on his knee with the largest smile and her jaw dropped. The easiest yes! Ryan and Caitlin were able to celebrate with a surprise engagement party that evening with all their family and friends.

The future Mr. & Mrs. Roycroft are looking forward to continue building their relationship and love with many fun memories along the way!

Things to Do

Things to Do coming soon!