5 hours ago
Benito Skinner and Terrence O’Connor End Nine-Year Relationship
READ TIME: 11 MIN.
On October 22, 2025, Benito Skinner—known professionally as Benny Drama—revealed during an episode of his podcast Ride that he and Terrence O’Connor had ended their romantic relationship after nine years together . Skinner paused the recording to deliver the news privately before resuming, a decision he explained was intended to prevent the moment from circulating widely on social media. “Terry and I are no longer together,” Skinner told listeners, adding, “I will say that we both just love each other so much and have so much love and respect for each other, and we treated each other with love and respect until the end” .
The announcement was met with an outpouring of support from fans, many of whom had followed the couple’s journey through social media and public appearances. The pair had become symbols of a modern, supportive LGBTQ+ relationship, with their breakup prompting jokes—and some genuine dismay—among followers who had invested emotionally in their story. Skinner addressed this directly, urging fans not to let the split shake their belief in love. “I think that if us breaking up makes you stop believing in love, I think it should be the opposite,” he said. “I was with someone so special to me for nine years in a committed relationship with my best friend. We loved and championed each other, we grew up together in so many ways” .
Skinner and O’Connor first met at a party in New York City in 2016, both newly out and navigating their early careers in the creative industries . Their relationship quickly became a source of inspiration for many LGBTQ+ people, who saw in them a model of mutual support and creative collaboration. O’Connor, a creative director, played a role in shaping the Brat era with musician Charli XCX, while Skinner’s work as a comedian and writer, including his series Overcompensating, benefited from O’Connor’s input on marketing and creative direction .
The couple’s visibility was notable in an era when public LGBTQ+ relationships, especially among men, remain less common in mainstream media than their heterosexual counterparts. Their openness about their partnership—shared through social media, interviews, and public appearances—helped normalize same-sex relationships for a broad audience. This visibility also carried a sense of responsibility, as both men acknowledged the impact their relationship had on fans who looked to them for representation and hope.
Skinner and O’Connor have been careful to frame their separation as amicable, with no suggestion of wrongdoing or conflict. “There was no foul play,” Skinner emphasized on Ride, with co-host Mary Beth Barone echoing the sentiment . Both expressed a desire for the other’s happiness and continued success, underscoring the maturity and mutual care that characterized their relationship’s conclusion.
This approach stands in contrast to the often sensationalized coverage of celebrity breakups, particularly those involving LGBTQ+ couples. By prioritizing privacy and respect, Skinner and O’Connor have set a precedent for how such transitions can be handled with dignity, even under public scrutiny.
As both men move forward in their personal and professional lives, their legacy as a couple who modeled respect, creativity, and openness will likely endure. Skinner has indicated that O’Connor will remain “a friend of this pod,” referencing his podcast Ride, and has affectionately referred to him as “Grandpa Terry forever,” a nod to their shared history and ongoing connection .
Their story is a testament to the evolving nature of LGBTQ+ representation in media and culture. While their romantic partnership has ended, the impact of their visibility and the example they set for healthy, respectful relationships will continue to inspire.
