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This Terry And Benny Breakup News Just Ruined My Day

Home> Entertainment

Updated 11:14 24 Feb 2026 GMTPublished 18:16 22 Oct 2025 GMT+1

This Terry And Benny Breakup News Just Ruined My Day

Please check in on your friends who listen to 'Ride' and/or Charli XCX.

Ilana Frost

Ilana Frost

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Featured Image Credit: Getty

Topics: Celebs, Social Media

Ilana Frost
Ilana Frost

Ilana Frost is an entertainment writer at Betches. As a teenage girl in her twenties, she spends her time stanning Olivia Rodrigo, baking cakes for award shows, and refusing to ever leave her Reputation era.

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Everyone in my life needs to be gentle with me today as I mourn the loss of Benny Skinner and Terry O’Connor’s romance. Yup, the Overcompensating creator and the creative director just broke up after nine beautiful years together.

The two icons first crossed paths at a party back in 2016, both newly out of the closet and newly arrived in New York City. Sparks flew instantly, and a real-life rom-com followed. “I really had a That’s So Raven moment where I was immediately like, ‘I’m going to marry him,’” Terry told Nylon earlier this year. While they won’t be walking down the aisle after all, their relationship was filled with love, creativity, and mutual support. (Benny got to cheer on Terry as he helped shape the Brat era with Charli XCX, and Terry consulted on the marketing for Overcompensating.)

I’m devastated and need to know: why did Benny and Terry break up? Here’s what they’ve shared about the split so far.

Why Did Benito Skinner And Terrence O’Connor Break Up?

Benito Skinner’s Statement About Terrence O’Connor Breakup

Terry O'Connor and Benito Skinner
Terry O'Connor and Benito Skinner
Image Credit: Getty

Benny addressed the breakup right at the beginning of the October 22 Ride episode. He cut cameras for a few minutes in order to avoid that clip making the rounds on social media (so understandable). “Terry and I are no longer together,” the writer and comedian revealed. “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.”

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Unfortunately, fans of the show have previously joked(?) that they would stop believing in love or even unalive themselves if Benny and Terry ever broke up. During the pod, Benny strongly discouraged fans from doing either of those things. “I think that if us breaking up makes you stop believing in love, I think it should be the opposite,” he told Ride listeners. “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.” Benny added, “I feel so unbelievably lucky to have met him and be a part of his family.” ‘Scuse me while I go sob.

The silver lining? This sounds like the most amicable breakup ever. “I really feel so lucky to have met him and be around his genius,” Benny said about his now-ex, Terry. “He is always a friend of this pod. Grandpa Terry forever.” He and his Ride co-host, Mary Beth Barone, emphasized that there was “no foul play” and they all just want the best for each other.

While it’s difficult for me to believe in love after this particular breakup, I’m gonna try because Benny said to. Wishing both of them all the best!

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