If you know us, you know we're obsessed (bleep it) with Benito Skinner. From his podcast to his Instagram skits, we eat up everything the comedian puts into the universe. Naturally, news of his debut series, Overcompensating, was music to our ears, and we were quick to watch the first season in its entirety. But an Overcompensating-shaped hole has loomed large in our lives since the credits rolled on the final episode, and we've been dreaming of the day season two might finally get confirmed. Now, it's finally been filled — with season two en route. Here's what we know.
Filming has wrapped on season two
All is (nearly) right in the world again. Benny confirmed that filming had wrapped on season two, but also warned that there was still editing to be done. In the meantime, Ride the podcast (finally) returns on July 15, so at least there's that to keep us entertained.
View this post on Instagram
Zedd is set to make a cameo
Season one gave us Charli XCX, so it's only fitting that someone equally iconic takes the reigns in season two. Who better than Dj and producer Zedd? Speaking on stage at Prime Video's Obsessed-Fest, Skinner gave a little more insight into the guest role.
“I was thinking about the time period that inspired this show,” he said. “So, we do have a special guest, and it’s Zedd. We have Zedd for Spring Break, so Zedd will be playing ‘Clarity’. I can’t tell you where he plays it, but it’s inspired a little bit by Fyre Festival.”
Benito plays two characters in the upcoming season
Look, we don't know what this means exactly, but it came from Skinner's mouth at Obsessed-Fest. “I do play two characters this season,” he told Deadline, adding, “Yeah, there’s something coming, something sinister.”
Australian Aisha Dee was just added to the cast
She's one of several new recurring cast additions, including AnnaSophia Robb and Tom Francis.
Dee is playing a character called Naomi, while Francis will play Declan Bishop, and Robb will play Chels.
The other major casting news is that Holmes' iconic character Hailee, has been promoted to a series regular. Thank god.
View this post on Instagram
Season two was confirmed in late 2025
Skinner took to Instagram to share the news, finally putting an end to mounting speculation about the fate of the series.
"WE’RE OFFICIALLY GOING BACK 2 SCHOOL," he wrote. "Thank you so much for all your insane love for this show. And thank you for being so patient while Daddy’s been cooking season 2."
View this post on Instagram
Long before season two was made concrete, rumours were swirling that a writers room had already been formed. Film Updates reported that a writers room for the second season was "in progress" back in July, and Amazon had been "praising the show’s passionate fanbase and strong completion rates." They were quick to temper this news by saying that show hadn't been formally renewed, however the outlet also said that conversations were ongoing, and an outcome was expected imminently.
When will season two come out?
This much remains to be seen. The latest update comes courtesy of Kyle McLachlan, who starred in season one as Skinner's dad. Speaking on the red carpet at the premiere of Fallout season 2, he said, “I know that Benny and the group are in the writers room, and I know they’re working away. But I am as curious as you are about what they have up their sleeve, so we’ll see. I mean, whatever it is, it’ll be great.”
We know season one (which is loosely based on Skinner's own coming out story) took around five years to develop. We're hopeful that the season two timeline might be a little shorter, but we'll keep you updated when we know more.
Benny teased a second season on TikTok
Skinner soft-launched the idea of a second season on TikTok, where he posted a video with friend and Overcompensating cast member Owen Thiele dancing, writing simply: "Benny in season 2..."
It goes without saying that the comment section went into overdrive, with users commenting, "Is this how you confirm season 2???" and, "This better be your way of announcing a season two."
@bennydrama7 so there’s this bottom… @owen thiele ♬ Originalton - theholyfabio
Season two could feature a cameo from Terry's mum
If you're a fan of Skinner, chances are you also love his ex-boyfriend, Terry O'Connor. O'Connor is a photographer and creative (credited with Charli xcx's Brat rollout), and he (and his mum) are a frequent topic of conversation on Skinner's social media. When we chatted with Skinner about the possibility of a cameo from Skinner's mum, he shared: "We tried to get Terry's mum in this, but she had a tee time.... She's very busy right now."
@russhmagazine Petition for @terrencefoconnor’s to mum make an appearance in #Overcompensating season two @Benito Skinner ♬ original sound - RUSSH Magazine
Feature image via Instagram.
