Bailee Henderson, known for her appearance on the ninth season of Summer House, is celebrating a major milestone in her personal life. The New York City-based influencer announced her engagement to her boyfriend, who goes by Shiv on social media, during a romantic trip to Kenya. Henderson shared the joyful news in an Instagram post on Monday, June 16, captioning a series of selfies with her fiancé, “I get to spend the rest of my life with my best friend🥹❤️.”
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The couple’s engagement photos captured their undeniable happiness, with Henderson proudly displaying her sparkling engagement ring. In one image, the pair gazed lovingly into each other’s eyes, radiating joy. A follow-up video offered a closer look at the stunning ring as Henderson and Shiv held hands, sealing the moment with their shared excitement.
Henderson also took to TikTok to share the news, where she has been documenting their unforgettable safari adventure. In a heartfelt video, she exclaimed, “Guys, it happened. I’ve been crying all day,” while showing off her ring. When asked how it felt to have a fiancée, Shiv responded with a smile, “It feels the same. Honestly, I knew you were going to be mine the moment I met you.” Henderson captioned the post, “I’m so happy you have no idea!! This week has been beyond magical.”
In a second TikTok video, Henderson expressed gratitude for the outpouring of love from her followers, admitting she “still can’t believe it.” Playfully, she added, “Who would’ve thought that a man would want to put a ring on this?” before expressing her overwhelming joy, saying, “I can’t get over this.”
Despite her brief time on Summer House, Henderson remains close with several castmates, who were quick to celebrate her engagement. Amanda Batula commented, “Yayyyy congratulations,” on her Instagram post, while Ciara Miller wrote, “Congrats Bailee!! ❤️❤️❤️.” Lexi Wood, another former Summer House star, added, “Soooo happy for you!!!!!!!❤️❤️.” Paige DeSorbo also joined the celebration on TikTok, commenting, “I’m so happy for you !!!”
Henderson has frequently shared glimpses of her relationship with Shiv on TikTok, including a video in May where she predicted the engagement. In the clip, which marked the start of her “countdown to Kenya,” she told followers, “I think I might be getting engaged.” Reflecting on their love story, she revealed that the couple first met at Tompkins Square Park in New York City. At the time, both were casually seeing other people but bonded over feeling like something was missing in their relationships. “We talked to each other, like, about our relationships and everything, how we were just … we felt like we were missing something,” she shared.
Their connection quickly deepened, and soon after they began dating, Henderson confided in Shiv about her lifelong dream of going on a safari. Little did she know, that dream trip would become the backdrop for a life-changing proposal. What started as an adventure to explore Kenya’s wildlife turned into a moment Henderson will cherish forever—a sparkling ring and a promise to spend the rest of her life with her best friend.