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Caroline & Lyla – A Romantic Proposal at Tiehack Mountain

Caroline & Lyla – A Romantic Proposal at Tiehack Mountain

Jessica Sinatra Photography captured a North Andover lesbian proposal (1)

On top of Tiehack Mountain, Aspen, Lyla gave Caroline a personalized cartoon book about their relationship – a perfect proposal.

Tell us about planning your proposal together.

We planned some logistics together but wanted to have some surprises. Lyla surprised Caroline with a personalized cartoon book of our relationship. Caroline surprised Lyla with a long letter about our love story.

We hiked to the top of our favorite mountain in Aspen. At the top, when Lyla gave Caroline the personalized book, our dog Ollie got too excited and knocked coffee all over it. We had a good laugh, and it now has memorable coffee stains on it.

What led you to Aspen?

It’s our favorite mountain, Tiehack Mountain, and we’ve hiked it together almost every year of our relationship. Lyla lost her dad in 2020, and we spread some of his ashes at the top of the mountain. We wanted Lyla’s dad to be part of the day, as he was one of the biggest cheerleaders of our relationship. That mountain, and Aspen in general, are really special to us—it’s a place where we get to spend lots of time with Caroline’s family.

Tell us about the engagement ring experience.

We worked on the rings together—designing the style and picking our center stones (or, for Caroline, five stones), but we left the final design as a surprise. Lyla’s best friend introduced us to her grand-uncle, Brad Gamss, who owns Rahl Jewelers. He was incredible and worked with us on each step to create our perfect rings.

What does your engagement mean to you both? Has anything changed?

We’ve known for a while that we would be together forever (Lyla knew from the start), so our engagement was really a formal promise and the fruition of what we’ve known. We’ve both done a lot of growth as individuals throughout our relationship. And our engagement signals our progress and that we will always work on ourselves.

How is wedding planning going? What do you hope for your wedding to be like?

Thanks to our wedding planner, and our moms, it’s going smooth and has been a hugely enjoyable process so far! We want our wedding to be a time for the people we love to all come together and celebrate one of life’s greatest joys—true love and partnership. It’s been both a joyful and challenging time since the pandemic—we both lost people in the past few years whom we love dearly. Time is a precious commodity, and our wedding is a special moment to all be together. It also signifies our lifelong commitment to each other and the life we’re building together.

How are you going about choosing your key vendors?

We’ve been prioritizing women-identified vendors and businesses. Supporting vendors and businesses of color has also been important to us. Our wedding planner has helped us find both classic and unique approaches to the important things—capturing the memories and making sure everyone has fun.


Photography by Jessica Sinatra

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