For many of us, high school is a time that we’d prefer to forget, rather than celebrate. Unlike most versions of it we see on shows on the CW, generally speaking, high school for most was an awkward, gangly, acne-scarred mish-mash of memories good, bad and ugly. Thankfully, writer-director Maggie Carey’s new coming-of-age comedy (or cumming-of-age if you’re nasty), The To Do List, doesn’t shy away from the uncomfortable moments that make our high school years such a formative experience. The film follows Brandy Clark (Parks and Recreation‘s Aubrey Plaza), a straitlaced, straight-A student who is determined to give herself a sexual education that will rival her academic expertise before shipping off to to college in the fall. The sex comedy was originally titled The Hand Job, just to give you a sense of the kind of experience you’re in for.

Carey, married to SNL alum and The To Do List co-star Bill Hader, padded out the cast with a hilariously endearing ensemble including Alia Shawkat, Scott Porter, Rachel Bilson, Connie Britton, Clark Gregg, Donald Glover and more that embraced the film’s early ’90s aesthetic and hit the ground running with it to complete the film in only 24 days. At last week’s San Diego Comic-Con, Nerdist News’ editor-in-chief Brian Walton and I sat down with Carey and stars Aubrey Plaza, Alia Shawkat, Rachel Bilson and Scott Porter to talk about what they geeked out to in the nineties, and their embarrassing early sexual experiences. Plus, we’ve got an exclusive new trailer for the film, which opens in theaters nationwide on Friday, July 26th.

Nerdist: So, The To Do List takes place in the Nineties, and it’s about you, [Aubrey], going out and trying to fulfill some needs before going off to college

Rachel Bilson: That’s a nice way to put it. Just fillin’ some needs!

Scott Porter: I don’t know if she’s filling some needs or filling some other things…

N: Unlocking achievements?

Scott Porter: Yeah, some cheevos. Handy J – that’s a hundred g’s.

Rachel Bilson: We all have needs that need to be fulfilled.

N: Duly noted. What appealed to you about doing the movie? How did you relate to the character?

Aubrey Plaza: Well, I never read a script about a girl going through all of her firsts before that portrayed it in such an honest and funny way, so that’s what appealed to me about it. Also, it’s just really funny in general and I relate to a lot of things about the character. I think every girl goes through a point in her life where she has to give a handjob for the first time. I remember that moment in my life and I just wanted to do that on screen and have everyone watch.

Alia Shawkat: That’s why you’re so special, Aubrey.

Aubrey Plaza: Thanks.

N: The sex comedy genre has been very male-dominated for years and movies like American Pie have created so many clones over time. When you’re crafting a film like that, how do go about making it more intelligent and gearing it towards an audience with a different perspective? Did you look at other movies? Were you trying to avoid certain things?

Maggie Carey: Well, first of all, I love American Pie. I think that’s an awesome movie and I remember seeing it in the theaters and really liking it. I’m absolutely a fan of this genre of movies – Dazed and Confused, Fast Times at Ridgemont High, American Graffiti – and I also grew up on John Hughes movies, so Breakfast Club, Pretty in Pink, Sixteen Candles…come on! Honestly, when I was writing, I was just writing a story and Aubrey already talked about the handjob thing. I think that you write what you know; I know Boise, Idaho in 1993 and I know…I know handjobs.

To be frank, the first handjob I gave had a bigger impact on me than when I actually lost my virginity, so there was something slightly inherently funny or odd about that, so I kind of held on to it and then wrote from there. I didn’t set out to change a genre. I was merely writing and I think because I am a girl that it came from that perspective.

N: Very nice. Catch us up a bit – who are you guys playing in the film?

Scott Porter: Rusty Waters, grunge rock lifeguard. He’s out of college and he’s a lifeguard at a community pool. He has huge aspirations to be a grunge rock superstar and he’s doing so by serenading girls at high school parties. He’s kind of that guy who left high school as the top dog and couldn’t move on in a way. But, he’s got long golden locks and that can get you pretty far in this world.

N: Continuing your trend of playing musicians.

Scott Porter: Yeah, it’s my third time singing or playing guitar in a movie and I dig it every time. This one especially because I felt like I was in a Whitesnake video with Aubrey doing her step-touch-sway movement. I felt like I had that girl that was just looking at me so longingly and I’m up there with my guitar, just rockin’, with a fan on me, backlit. Yeah, that’s pretty amazing. This might be my favorite video I’ve shot.

Maggie Carey: He requested all of that in the studio when we recorded it too. He was like, “I will sing, but only with a fan,” so it got on the audio a little bit.

N: When you’ve already done what you did at the beginning of Music and Lyrics, you kind of have to bring your A-game, right?

Scott Porter: Yeah, I’ve done a couple of decades worth. I did an ’80s pop star, a ’90s grunge rocker and a Bruce Springsteen cover band called Ben Wheatley and the Glory Dogs, so I’ve done some pretty fun stuff.

Rachel Bilson: You’re typecast.

Scott Porter: I’ll be typecast as a bit of a rockstar. Why not?

Aubrey Plaza: There’s worse things.

Scott Porter: There’s worse things for sure.

N: And you, Rachel, what attracted you to your character?

Rachel Bilson: Well, my character…

N: We’re not saying you were attracted to your character…

Rachel Bilson: I was extremely attracted to my character. I’m Aubrey’s older sister; I’m very smart when it comes to sex, so I definitely impart some wisdom on her. I don’t know…

Aubrey Plaza: You did. You still do.

Rachel Bilson: I still do.

Maggie Carey: Give us a tip right now.

N: Straight out of UrbanDictionary.

Rachel Bilson: “Circular motions.” No. Never mind. Anyway, my character is very funny, very stereotypical 90210-era of ’90s – the hair, the outfit, everything.

N: That was the decade we all bought in. Everyone was copying everything, so it’s kind of awesome you guys had that level of detail.

Maggie Carey: Yeah, I gave the production designer photos of my high school girlfriends and me in our rooms and they really ran with it. [Rachel’s] room is like mint green and peach. It looks like it came straight out of Miami. I think that’s what we were wishing for in Idaho – anything on either coast was cool.

N: Feel free to pass on this one – tell us about one of your earliest sexual experiences, be it a kiss or otherwise. Was it awkward? Memorable? Did it inform how you approached the film?

Scott Porter: There was a girl I had a crush on across the street – I was like eleven years old – and I wanted to kiss her, but I didn’t know how to go about asking to kiss. You couldn’t just go to the movies or anything, so we had this game of tag, but then we morphed it into a game where in order to tag the other person, you had to furiously make out with them. And it was like an eleven year-old orgy – I just wanted to kiss one girl, but suddenly it was like forty kids all making out. None of the guys would tag the other guys; it was a really interesting…I learned a lot that day at eleven.

Maggie Carey: It’s that sort of Truth or Dare-style safety in numbers. We would play something called Chicken and this was in tents in Idaho; it was how we snuck boys over. You would play Chicken in front of your friend and basically the boy would take his hand and slowly work his way up your body while saying, “Chicken? Chicken? Chicken?” Maybe he’d go under your shirt, maybe he’d touch your padded bra from K-Mart. There was safety in numbers. I think for us it wasn’t as much sexual as it was about curiosity. Let’s just say it wasn’t pleasurable.

Scott Porter: We played that game too, but we called it “Do You Trust Me?” and you had to get a yes or no answer. If the girl was like, “Yes” then you moved up and once you got to the point of no return, it was like, “It’s on!”

Maggie Carey: Alia? What about you? You’ve been quiet.

Alia Shawkat: [whispering] I lost my voice.

Aubrey Plaza: Safety in numbers…I never experienced that. Group…sexual…

N: The Eighties pretty much showed how that works. Why don’t you tell us about your character, Alia? You’re the wingman, correct?

Alia Shawkat: Yeah! My name’s Fiona – let’s start with that. She’s kind of a board you bounce things off of and she has a little more experience than Brandy, so she’s kind of pulling her down and building her up, which is the kind of thing that friends do to each other in high school.

N: Is it the type of thing where she’s trying to one-up her?

Alia Shawkat: Yeah, kind of. That stuff doesn’t happen in the film, but I like to think it happened off-camera. It’s the sort of thing where she’s a good friend and a bit flabbergasted – that’s a big word – by the fact that her friend’s moving so fast sexually because Brandy’s not like that.

N: You guys all seem to be getting along quite well and have a good dynamic. What was the tenor of the set like? 

Maggie Carey: They’ll probably have a different perspective, but it was a really low-budget indie movie and we shot it in 24 days and did 6-day weeks and all of our cast is also on TV shows, so we were begging them to come back. Some of them were coming back and forth from their shows. I had a lot of fun, but I also know it was like 110 degrees in the Valley in the heat. It was hot. For me, it felt like film camp, like summer camp in a way.

Aubrey Plaza: It was kind of like summer camp. It was at a community pool in the Valley and everyone was running around…

Maggie Carey: The food was summer camp quality.

N: We’re talking Chatsworth-level Valley, right?

Rachel Bilson: Yeah, like Woodland Hills.

N: So, were you able to do any improvisation on set in spite of the shortened schedule?

Maggie Carey: Yes! The movie is definitely scripted, but absolutely with a cast like this? Yes, please. We try to leave room for improvisation or have certain conversations beforehand. Like Aubrey, the husband pillow – the way she humped it wasn’t scripted.

Aubrey Plaza: Yeah, a little bit of physical improvisation.

Maggie Carey: I’d say there’s a lot of scripted jokes, but the cast rose to the occasion.

N: Do you have a favorite unscripted bit that didn’t make it into the final cut? Or just a favorite moment on set?

Scott Porter: I like the supercuts of me playing with juggle sticks.

Scott mimes a very intense move with his devil sticks.

Maggie Carey: He actually learned how to use them, juggle sticks – devil sticks for some people – and Scott actually learned how to do it. There’s a lot of wonderful moments, but I really love the subtleties between the characters like when the three best friends are sitting at the table talking about the pearl necklace and Aubrey gently caresses her neck. Or Scott, when he was using the devil sticks, you did it with such sincerity. I really like those moments.

N: One final question to wrap things up – Cameron Crowe or John Hughes?

Scott Porter: John Hughes.

Rachel Bilson: That’s a tough one, that’s really tough.

Maggie Carey: I’m John Hughes. However, Singles is so incredible. Almost Famous…

Rachel Bilson: Say Anything!

N: Fast Times at Ridgemont High.

Alia Shawkat: Not the Orlando Bloom and Kirsten Dunst one though. No one saw that right?

N: Elizabethtown? [Brian] grew up in that area, so [he] saw it.

Alia: Yeah, that was a winner.

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You can catch The To Do List in theaters nationwide on Friday, July 26th, and watch an exclusive Old People Reaction Spot. Are you excited for the film? What was your favorite part of the Nineties? Let us know in the comments below!

Additional reporting by Brian Walton.