As a medevac helicopter pilot and a critical care transport nurse, Orla and Jess’s love story began at work. While their story started with friendship, over time their bond grew into the relationship they both had been waiting for their whole lives!

Jess introduced Orla to the show The Office, where the love story between Jim and Pam unfolds. In so many ways, Jess and Orla are the Jim and Pam of their own love story. (Love that!) The couple got engaged in Ireland, which holds deep meaning for Orla, as both of her parents were born there, and her mother was buried there. Jess proposed on the Cliffs of Moher, a stunning and unforgettable location for the both of them.

A Pink-Themed Party with Heart Sunglasses, Bluegrass Beats, and All the Joy

As a couple who spent so much time outdoors– skiing, hiking, and embracing every season and activity together- picking  Vermont, and ultimately, Squabetty as their wedding location was an easy choice; it truly felt like home! Jess and Orla knew from the start that they wanted their wedding day to be vibrant, joyful, and full of personality. To set the tone, they chose a lively bluegrass band that kept the energy high throughout the celebration. They also encouraged guests to lean into a playful pink dress code—and let’s just say, everyone understood the assignment! Before the festivities kicked off, Orla got ready with her bridesmaids in matching robes and fun heart-shaped sunglasses, setting the stage for a morning filled with laughter and anticipation ahead of the couple’s sweet first look.

Moving violin music played as Orla and Jess came together for their ceremony, sharing vows that expressed a love deeper than they had ever imagined before meeting one another. They stood beneath a unique triangle arch (its shape mirroring the surrounding mountain peaks!), creating a striking focal point. Following the ceremony, guests enjoyed a relaxed cocktail hour complete with lawn games, cozy lounge seating, and a spread of delicious bites from Caja Madera. With gorgeous pops of color and vintage charm, courtesy of Orla’s epic thrifting and collecting skills, this wedding was truly an event bursting with charm! 

The celebration continued in a beautifully decorated event barn, adorned with lush florals by Pistil Production, personal photos, and vintage glassware collected throughout the planning process. One of the most important elements of Orla and Jess’s wedding was a memorial table dedicated to Orla’s mother and best friend. We also love the couple’s epic dessert display, crowned with a custom cake topper that paid homage to the couple’s shared careers, a personal and meaningful detail that guests won’t soon forget.

While their wedding day was certainly memorable on its own, the most unforgettable moments were the love, support, and help the couple received from their friends and family. Congratulations, Orla and Jess!