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Tyler & Kylee

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Tyler Hayden

and

Kylee Lessard

June 29, 2025

Hood River, OR
47 days47 d12 hours12 h49 minutes49 min58 seconds58 s

How We Met

A Modern Fairytale

Tyler and Kylee's love story began on January 1, 2020, with a right swipe on Hinge. Tyler had a “rule of three” for first dates: interact in three different environments to get to know someone better. He took Kylee out for tacos, ice cream, and a walk near Dolores Park. Kylee’s first thought? “Whoa, he’s tall!” Tyler was impressed by Kylee's commitment to Dry January and joined her. The date was wonderful, but Kylee was puzzled why he didn’t kiss her goodnight. Tyler, ever the rule-follower, also had a “no kiss on the first date” rule. By the third date, though, Kylee knew Tyler would be her boyfriend. Her intuition didn’t fail her. It seemed Tyler’s rules were working out well, after all.

Our First Years Together

A Tropical Love Story in the Time of COVID

Though the world shut down within their first few months together, the pandemic only brought them closer together. They spent a blissful month seeing only one another, and about six months into dating, decided to move to Hawaii together. They settled into Kylee’s grandparents’ empty house in the remote, idyllic Kaneohe Bay, where life was a dream—kayaking, exploring lush hiking trails, and reading on the beach to reggae music. It was on a moonlit kayak ride that Tyler first knew he would be with Kylee for the rest of his life. They loved their time in Hawaii so much that they signed a lease on an apartment in downtown Honolulu with stunning ocean views.

The Proposal

TyKy Adventures & A Malibu Surprise

After a year in paradise, they moved back to San Francisco, filling their days with community, reading in the park, yoga, new restaurants, and trying every monthly flavor at Salt & Straw. They traveled internationally for the first time to Costa Rica, Europe, and Banff. Despite Tyler’s allergies, Kylee convinced him to start fostering kittens, bringing endless joy to their household. After four years together, Tyler planned the ultimate surprise proposal during a "girls’ trip" to LA. He met Kylee at the end of a pier in Malibu Beach with a ring in hand, a photographer to capture the moment, and eight of her best friends there to witness it. It was the proposal (and ring!) of Kylee's dreams.

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For all the days along the way
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