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Jake & Ryley

August 2, 2025 • Elkhorn, WI

Jake & Ryley

August 2, 2025 • Elkhorn, WI

Our Story

Ryley meets Tommie Trewyn (Jake’s dad)

Picture of Ryley meets Tommie Trewyn (Jake’s dad)

In 2016, Ryley was talked into joining the high school softball team by coaches Steve, Tommie, and Hughy.

Long story short, Ryley and Tommie became fast friends — and before long, it became a running joke that Tommie would say, ‘You should date my son Jake.’

Well… turns out Tommie had a pretty great idea. Thanks, Tommie!

Rugby

Picture of Rugby

Jake’s parents, Tommie and Sara, continued to cheer Ryley on throughout her collegiate rugby career — and they didn’t let up on trying to convince her to date Jake!

Pictured here after a rugby match at Sobelmans in Milwaukee, WI.

Jake & Ryley finally agree to a date!

Picture of Jake & Ryley finally agree to a date!
In May 2023, Jake finally took Ryley out on their first date in Milwaukee, WI. He always said he was waiting for her to graduate before making his move — and sure enough, this photo was taken right after Ryley’s college graduation.

Dating

Picture of Dating

Jake and Ryley quickly became inseparable.

Pictured here at Gabbie (Jake’s sister) and Zach Wollert’s wedding.

Jake & Ryley get engaged!

Picture of Jake & Ryley get engaged!

In December 2023, Jake proposed to Ryley at a Christmas lights festival, surrounded by their parents — Tommie, Sara, Rick, and Gina. It was cold and rainy, but to Jake and Ryley, it couldn’t have been more perfect.

They both agree it was love at first sight and knew shortly after their first date that they had found ‘the one.’

Truly, the best day ever!

Purchased a home!

Picture of Purchased a home!

In February 2024, Jake and Ryley closed on their first home (with help from Aunt Mindy — thanks again!) in Beloit, WI.

With the engagement and rent adding up, they figured it was the perfect next step to start their life together.

Our baby Winnie

Picture of Our baby Winnie
In May 2024, we welcomed a Golden Retriever puppy named Winnie into our lives. Since then, we’ve been enjoying our home, our puppy, each other’s company, and all the fun (and chaos) of wedding planning! We can’t wait to celebrate our special day with you.