Entertainment

Kaitlyn Bristowe Reveals Unforgettable First Time to Colton Underwood

Kaitlyn Bristowe Reveals Unforgettable First Time to Colton Underwood
Editorial
  • PublishedAugust 23, 2025

Kaitlyn Bristowe candidly shared her experiences about losing her virginity during a recent episode of the new Hulu dating show, Are You My First?, co-hosted by Colton Underwood. The conversation unfolded as they played a game designed to explore their first experiences, with Bristowe describing her inaugural encounter in three words: “scary, painful, and terrible.”

During the discussion, Underwood, 33, prompted Bristowe, 40, for more details. She reminisced about her first kiss, recalling a significant moment marked by the song “When the Lights Go Out” by the British boy band Five, released in 1998. In stark contrast, Bristowe described her first sexual experience as an awkward silence on the couch, specifically on a “hand-me-down” couch from her sister, which had been a remnant of their parents’ divorce.

Bristowe explained that the experience, while meaningful with her high school boyfriend, was overshadowed by her struggle with a condition known as vaginismus. This medical issue, characterized by involuntary muscle contractions causing pain during penetration, added a layer of difficulty to a moment she once envisioned as romantic. “Honestly, it was like a horror film, and I say this with love,” Bristowe remarked, emphasizing that while it was with someone she loved, the reality did not match her expectations.

She further elaborated on her reflections about intimacy, offering advice to those navigating their own romantic journeys. “It’s not going to be sexy. It’s messy, but so is love,” she stated, highlighting the often-unspoken truths about first experiences. Colton responded positively to her insights, acknowledging their value for the audience.

Bristowe and Underwood, both veterans of the Bachelor Nation, have taken on the role of guides for contestants in Are You My First?, which aims to explore the nuances of first romantic experiences. Underwood clarified that the show’s objective is not solely to facilitate sexual encounters but to foster meaningful connections. “The goal is to connect with somebody, to experience these things,” he noted.

The show also aims to promote self-love and acceptance among participants, encouraging a deeper understanding of their virginity and personal journeys. “People experienced their firsts on Are You My First? in different ways,” Underwood explained, reinforcing the notion that each individual’s path is unique.

As the series continues to stream on Hulu, Bristowe’s and Underwood’s discussions resonate with viewers, providing a blend of personal insight and entertainment that aims to normalize conversations around first times. Their shared experiences and openness contribute to a broader dialogue about intimacy, relationships, and the complexities that often accompany them.

Editorial
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Editorial

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