Beloved internet personality and Overcompensating star Benito Skinner, known to many as Benny Drama, and creative director Terrence O’Connor have announced their separation after nine years together. Their relationship, built on love, respect, and even professional collaboration, has been a significant part of their public personas, leading to an emotional announcement that has deeply resonated with their dedicated fanbase.
The internet was abuzz on October 22, 2025, when Benito Skinner, the charismatic force behind Benny Drama and star of the hit series Overcompensating, shared a deeply personal update. On an episode of his podcast, RIDE, co-hosted with his friend and fellow comedian Mary Beth Barone, Skinner revealed that he and his long-term partner, Terrence O’Connor, had decided to go their separate ways after nine years of dating.
The announcement quickly traveled through social media, touching the hearts of countless fans who had followed their journey. Skinner, 31, emphasized that the split was “amicable” and rooted in a continuing profound love and respect for one another. “Terry and I are no longer together,” Skinner stated, adding, “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.”
A Decade of Shared Growth and Enduring Connection
Skinner reflected on the significant role O’Connor played in his life, particularly throughout his twenties. “We grew up together in so many ways,” he shared, expressing immense gratitude for their time together. “I feel so unbelievably lucky to have met him and to be a part of his family. I love his family. I love the cousins. So I hope that if anything, you should believe in love, because I really had it and I really feel so lucky to have met him and to have been around his genius.” This heartfelt sentiment underlined the deep bond that characterized their relationship, a bond that clearly extended beyond romantic partnership to genuine friendship and familial connection.
Their story began in 2016 at a party, a meeting that Terrence O’Connor, a talented photographer and creative director, once described as an instantaneous connection. In an April interview with NYLON, O’Connor recalled, “I really had a That’s So Raven moment where I was immediately like, ‘I’m going to marry him.’” He even played a pivotal role in Skinner’s early career, suggesting they work on building his Instagram following when Skinner expressed his aspirations to be an actor.
Professional Partnership and Public Persona
Beyond their personal lives, Skinner and O’Connor also collaborated professionally. O’Connor notably consulted on the marketing for Skinner’s acclaimed series, Overcompensating, which premiered in May. Their relationship was a visible and celebrated aspect of their public lives, frequently featured across their social media platforms.
The profound investment of their followers in their relationship was not lost on Benito Skinner. He acknowledged the comments he had often seen: “Over the years, I’ve seen comments that say, ‘If you break up, I’ll stop believing in love.’” Skinner then offered a powerful counter-narrative, urging fans to find hope rather than despair in their separation. “I think that if us breaking up makes you stop believing in love — I think it should be the opposite because I was with someone so special to me for nine years in a committed relationship with my best friend.”
A Glimpse into the Future: Continued Success and Mutual Respect
Even amidst the emotional announcement, Skinner injected a moment of characteristic humor. “Yes, I did make him promise that he will never date an actor younger than me,” he joked, adding, “That was my one request, and he spit-shook on it. So I would love a little bit of privacy and respect for both of us.” This lighthearted remark highlighted the ongoing affection and understanding between the two.
The news of their split comes just a month after Prime Video greenlit Overcompensating for a second season, a testament to Skinner’s rising star power. The series, which follows the journey of a former football player coming to terms with his sexuality, has garnered critical acclaim for its humor, storytelling, and LGBTQIA+ representation, holding an impressive 93% rating on Rotten Tomatoes. This continued success ensures that both Benito Skinner and Terrence O’Connor, in their respective professional endeavors, have bright futures ahead. Their journey together may be ending, but the respect and love that defined their nine years will undoubtedly continue to inspire both them and their fans. People.com reported on the breakup and details of the announcement.
