Benito Skinner Peppered Overcompensating Season 2 Easter Eggs in Season 1

“As far as Benny's story, I'm still really sticking with the things that feel true to my queer experience,” says Skinner, part of Teen Vogue's New Hollywood Class of 2025.
Benito Skinner illustrated by Laura Passalacqua
Benito Skinner, illustrated by Laura Passalacqua.

Growing up in Idaho, Benito Skinner never thought he would be where he is today. That is — the creator, star, and writer behind Prime Video's Overcompensating, his semi-autobiographical show that depicts his coming out journey in college.

“I think the gay thing would scare him a little bit,” Skinner says when I ask what his teenage self would think of his life now. “Definitely a lot,” he immediately reassesses. “But I think he'd just be like, 'No f*cking way. That's literally, like, so gas.'”

Gas might be an understatement. Skinner has created a burgeoning comedic empire for himself, and it seems nearly impossible not to root for his continued success. He has a clear creative vision, a contagious passion for what he adores, and a quick wit matched with the type of bashful humbleness that can only be attributed to those of us who grew up in the Midwest. Now, as he looks to Overcompensating, season two, he's finding joy in the creative process.

Below, we speak to Benito Skinner as part of Teen Vogue's New Hollywood Class of 2025.


Teen Vogue: Congrats on a well-deserved season two order of Overcompensating. Now that season one has been out in the world for several months, how are you reflecting on it? Where are we at with season two?

Benito Skinner: I've been meeting with writers this week to finalize our writers' room, asking them what excited them about the show, what they latched onto. Everyone has a different answer, and I feel really proud of that.

It's been so overwhelming and the most gratifying creative experience that I didn't even know I could have. It's really hard to get people to sit down and watch a full show. I feel really lucky that people chose ours and championed it, and that we get to do it again. I'm so excited.

TV: As you go into the writers' room, where is your inspiration going to come from?

BS: It's very much still autobiographical in a lot of ways. I learned so much through making the first season. And now I also get to write for my cast, and that's really exciting for me.

As far as Benny's story, I'm still really sticking with the things that feel true to my queer experience. But for everyone else, we have so much more to say about college, and just wanting so badly to be loved, and being such a fool. Everyone's such a fool — so much so it kind of makes you sick writing it at times, and I just have to take a deep breath and be like, we're all fools. We just need someone to love us.

TV: When you say that you're writing for the cast, I'm reading between the lines and wondering if you're gonna make Grace gay. That's what I'm asking for.

BS: This is so funny. I can confirm I'm not.

I've loved those fan theories — those Miles bi-truthers, Grace bi-truthers. There was also a Benny/Peter fanfic, which I sent to Adam [DiMarco] and said, “Something to consider.” It's just funny, what people take away.

I will say, there are a few things that I did pepper in, and people have not picked up on. So I'm excited for them to watch season two and be like, “You told us this would happen.”

TV: That was one of my questions! If there were any Easter eggs you put in that people missed. Or something insignificant that you put a lot of thought into for no real reason, other than it made you laugh.

BS: No one's brought up the fact that Riley asked Grace to get mocktails and did the hands-covering-eyes monkey emoji. There's a lot within Hailee world that I haven't seen people pick up on.

Posters on walls are always telling you something, and also websites. If you look at what other people are saying, or other tabs open, I'm always having fun pitching jokes for that.

There's one kind of glaring thing, but it would give away something, so I'm not gonna say it.

TV: How many iterations of Overcompensating did you go through before you landed on what it is today?

BS: I wrote 98 drafts of the pilot. I could write it forever. I just love this world and pitching for it.

We reshot an extra scene of Hailee and Carmen meeting, and I remember writing that in two minutes — the “Latinx” joke, and roomie-a*s-bitch. I hadn't written for six months because we had shot it and edited it, and then we reshot this. That was the first time I had written a new scene knowing who the cast was, and knowing I was writing for Holmes and Wally, and the reactions that they would give each other. That was so much fun.

TV: You're a writer, an actor, a podcaster, a comedian… Is there anything else you want to try?

BS: A lot of the things I've been looking at right now are producing. There are a couple of projects that I've signed on to produce.

I really fell in love with writing and acting. I just did a few acting projects that I didn't write and had no part in the process of, and it felt so freeing. [Overcompensating] is so emotional to me in every way, and the passion I have for it is all-consuming at times, so it's so exciting for me to go into someone else's words and play with them. And now, having seen the other side of it — all the decisions that go into making a character — being able to make someone else's vision come to life… I think I still have so much to say within those categories before I jump ship.

I would love to be in the theater. I never allowed myself that in my life because I thought people would call me gay. But now, I say I'm gay, so it's time to let it rip.

TV: Can you tell me about the other projects that you're working on?

BS: I did a couple of cameos in some fun things coming out next year by people that I love so much. It felt like such a dream, and I'm excited for people to see that. I got to play very
character-y characters.

I'm writing a script right now with Mary Beth [Barone] and Owen Thiele that I'm very excited about. Kind of like a gay best friends comedy/dramedy. I'm just having the time of my life writing it.

The other projects I'm producing, I wish I could tell you, but I'm very excited about them. For one, I'm not even on camera. Can you believe it? It's business stuff.

TV: What inspires you when you're in a creative rut?

BS: Music helps me a lot, especially for Overcompensating because, listening to old playlists from when I was in school, I can immediately tap back into these emotions.

And then it's going to things, talking to people, having them say weird things to me, and I'm like, “Hailee would say that.” You have to go outside, go on a walk, play music, go to a weird event, and feel uncomfortable for an hour. I force myself to do that.

TV: What part does fashion play in your life? Where do you find your inspiration for putting things together?

BS: Fashion has always been such an outlet for me. I felt so lonely and strange growing up in Idaho, and then going to college, I was so inspired by American prep and this athleticism that I grew up with, and it was fun for me to take that and make it a little queer and sexy. Kind of like “boy next door,” but he's got a secret. I love a Pinterest board. I love finding an old catalog on eBay and just ripping through it—old Versace, Abercrombie, J.Crew catalogs.

TV: What do you think your teenage self would think of you today?

BS: Oh my God. I try to think of this a lot because it all goes by so fast. The fact that I get to do what I do and be out, and I love it… I feel really lucky to get to do this. This was just not on the menu for me, growing up in Idaho. I never thought that I would be an actor or writer and really do this and tell stories in this way. So whatever I did to have this, hell yeah.

This interview has been edited and condensed for clarity.