If you’ve spent any time scrolling through Instagram or TikTok in the last decade, you know Benito Skinner—better known as Benny Drama. He’s the guy who can transform into a Kardashian, a Lana Del Rey fan, or a frantic corporate assistant with just a wig and a dream. But for the longest time, there was one constant in his world that wasn't a character. His boyfriend.
Terrence O’Connor, better known as Terry, wasn't just a partner. He was the secret sauce. For nine years, they were the "it" couple of a very specific, very cool corner of the internet.
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But things changed recently.
On October 22, 2025, Benito dropped a bombshell on his RIDE podcast. He and Terry called it quits. It wasn't some messy, dramatic Hollywood blowout with leaked texts and shade. It was, in Benito's own words, "amicable." They basically grew up together, and then, they just... didn't.
Who Is Terrence O’Connor?
A lot of people think Terry was just "the boyfriend." That’s a mistake. Honestly, the guy is a creative powerhouse in his own right. Terry is a photographer and creative director who has basically shaped the visual identity of modern pop music.
Ever heard of a little album called Brat by Charli XCX? Yeah, Terry was deeply involved in that. He’s worked with:
- Charli XCX (he shot the Crash cover and helped with the Brat rollout)
- Lorde
- Troye Sivan
- Olivia Rodrigo
- HAIM
They met at a party back in 2016. Both were new to New York City. Both were newly out of the closet. Terry told Nylon that he had a "That’s So Raven" moment the second he saw Benito. He literally thought, I’m going to marry him. At the time, Benito was just a guy with a private Instagram who wanted to be an actor. Terry was the one who told him, "I don't know how to help you be an actor, but let's get you a following." He helped edit the early videos. He ran small ad campaigns. He was the strategist behind the Benny Drama empire before there even was an empire.
Why the Split Matters to Fans
Nine years is an eternity in internet time. When you’re together for nearly a decade, you’re not just a couple; you’re a brand. Fans were obsessed with their elaborate, high-production Halloween costumes (remember them as Ben & Jerry?).
When the news broke, the internet went into a bit of a tailspin. Some fans even joked about "not believing in love anymore." Benito actually addressed this directly on his podcast. He said that if anything, their breakup should make people believe in love more. Why? Because he spent nine years in a committed, respectful relationship with his best friend.
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The Terms of the Breakup
Benito and Terry seem to have the healthiest breakup in history. They even made a "parting promise." Benito joked that he made Terry "spit-shake" on a promise never to date an actor younger than him. It’s that classic Benny humor, but it also shows there’s still a lot of love there.
They were even seen together at Charli XCX’s wedding just a month before the announcement. No tension, no weirdness. Just two people who realize they’ve reached the end of a chapter.
Life After the Breakup
Benito is busier than ever. His show Overcompensating was recently greenlit for a second season on Prime Video. It’s a huge deal. The show is a semi-autobiographical look at his college years—a time before he met Terry.
Meanwhile, Terrence is stepping into his own spotlight. He recently did his first solo podcast interview on The Cutting Room Floor, where he reflected on the transition from being a "behind-the-scenes" force to finding his own voice.
What You Should Know Now
If you're looking for gossip or "tea," you won't find much here. This is a story about two guys who moved to LA together, conquered the internet together, and then decided to let each other go.
Here is the reality of the situation in 2026:
- Status: Single (amicably split).
- Duration: 2016 – 2025.
- Collaborations: They still respect each other's work; Terry even shot the cover art for the RIDE podcast.
- Privacy: Both have asked for space as they navigate their 30s as single men for the first time in nearly a decade.
If you’re a fan of either of them, the best way to support is to just keep watching the work. Watch Overcompensating Season 2. Follow Terry’s photography. They aren't a package deal anymore, but they're both doing pretty incredible things on their own.
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Sometimes the most "human" thing a celebrity can do is show us that not every ending has to be a disaster. Sometimes, you just finish the book and start a new one.
Actionable Insight: If you're going through a long-term split yourself, take a page out of the Benito/Terry playbook. Focus on "growing up together" rather than what went wrong. Prioritize your own creative projects and give yourself permission to be a "solo act" for a while.