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Benito Skinner, Known as Benny Drama, and Terrence O’Connor Break Up After 9 Years

Benito Skinner and Terrence O’Connor ended their nine-year relationship with mutual respect and love, emphasizing privacy and positive memories, Skinner said on his podcast.

  • On Wednesday , Benito Skinner announced on his RIDE podcast that he and Terrence O'Connor have split after nearly a decade together.
  • They first met in 2016 at a party where creative director Terrence O'Connor said he immediately felt he would marry Benito Skinner, and the pair were last seen publicly at Charli XCX's wedding last month.
  • Skinner framed the split as amicable, saying they treated each other with love and respect until the end and urged fans not to lose faith in love.
  • Though separating, Skinner said O'Connor will `always be a friend of this pod` and asked for privacy as O'Connor has not publicly commented on the split.
  • O'Connor's role behind the scenes shows he helped build Skinner's online career, advising on strategy as Overcompensating was renewed for a second season at Amazon Prime Video.
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Just Jared broke the news in on Wednesday, October 22, 2025.
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