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    Home»Money»I Went on a Friendship Anniversary Trip With My Best Friend; Worth It
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    I Went on a Friendship Anniversary Trip With My Best Friend; Worth It

    Press RoomBy Press RoomAugust 21, 2025No Comments3 Mins Read
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    Although many milestone vacations celebrate romantic anniversaries, my recent trip to Jamaica honored something I feel is just as important — 20 years of friendship with the girl I met in fourth grade.

    We were just 9 years old when we first became friends, and at the time, we bonded over “High School Musical” and a mutual distaste for the boys in our classes. From there, we grew up side by side, supporting each other through graduations, heartbreak, big moves across the country, and chasing our dreams.

    Now, on the cusp of turning 30, we decided to celebrate two decades of friendship with a 20th anniversary trip. My only regret is not doing something like this sooner.

    The trip allowed us to bond in ways that aren’t possible over FaceTime


    Chloe and her friend sip cocktails at an outdoor bar.

    One of the best parts of the trip was how much uninterrupted time we had together.

    Chloe Caldwell



    As bicoastal best friends who are both in long-term relationships, it’s not often we get to see each other one-on-one. When we do get together in person, our plans typically include larger groups of mutual friends or our significant others, which means less alone time to catch up.

    One of the best parts of this trip, however, was just how much uninterrupted time we had together. We spent our days sipping piña coladas, dancing on the beach, relaxing at the spa, and reflecting on how far we’ve come.

    We laughed a lot on our trip, but we also cried a little, too. Although we FaceTime often, it’s hard to have the same kind of deep conversations that we have in person over the phone.

    Things like how overwhelmed you’ve been feeling at work, how you’re struggling to find joy in things you used to love, or how weird and confusing it is to be almost 30 and still figuring things out don’t always come up organically on a call.

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    But by the end of the week, we were sharing new goals and aspirations we hadn’t gotten around to sharing during our FaceTime catch-ups.

    Our time away reminded me that platonic love is just as worthy of celebration as romantic love


    Chloe and her friend smile with their arms around each other on a beach.

    I believe we should be celebrating our friends just as loudly as we do our romantic partners.

    Chloe Caldwell



    Although romantic relationships are important and fulfilling, in my opinion, they aren’t the only ones worthy of commitment, communication, and celebratory milestone moments.

    We’re used to attending engagement parties and weddings to celebrate romantic connections, but I wholeheartedly believe that friendships should be equally celebrated.

    Whether it’s a birthday gathering, promotion, running a marathon, publishing a book, or “just because,” we should be celebrating our friends just as loudly as we do our romantic partners.

    During our time in Jamaica, it felt like my best friend and I were still those 9-year-old girls, making up dances on the playground. The familiarity and longevity of our relationship brought out the playful, giggly inner child in us both.

    Twenty years later, not much has changed between us. But this trip was a reminder that friendship is worth every plane ticket, late-night phone call, and piña colada shared on the sand.

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