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Rashida Jones filtered her own relationship history — and a few heart-wrenching break-ups — into this weekend’s Celeste and Jesse Forever , an L.A.-set look at one couple’s struggle to remain besties through separation, divorce, and the complicated disentanglement that follows the world’s best-worst break-up. Co-written with fellow actor Will McCormack, whom Jones dated for three weeks years ago, the sweet, affecting dramedy is peppered with moments inspired by real life events that carry Celeste through her journey of painful but necessary self-discovery — including one legendarily awful date with a guy who turned out to be, in Jones’ words, “a serial masturbator.” Like Celeste, Jones, who looks back on her past relationships as life lessons, has learned the hard way that not all love stories are meant to last. “I’m no better at break-ups,” she admits. “I haven’t gotten any stronger, I just try to learn my lesson in a way where I don’t have to re-learn it, and that’s the only thing I can do,” she says. As I was watching, I realized these are revelations you can only really have by experiencing them firsthand. Yeah, totally. Will always says, “The cure for the pain is the pain.” I hate when he says that, but I definitely feel like it’s the first step in real adulthood, when you’re like, “Oh, things are not going to be the way I thought they would.” In some ways they’re going to be better, and in some ways they’re going to be way worse. But regardless, I have no control over it, and my need to control it only makes it worse. It definitely came from a real place. It’s a very personal story for me, and hopefully it’s the kind of thing I can leave in the movie and leave behind. There’s so much truth in this movie. For instance: The crushing wisdom that is contained in Boyz II Men’s “On Bended Knee.” Was there an actual best-worst break-up for you that inspired the story? It’s definitely a composite of a lot of relationships for me, for Will, and for family members and friends. We just stole the best-worst parts. I definitely loved somebody for years, and it didn’t work out. We grew up together, and it was really hard to let go. We spent years not being friends and now we’re friends and it’s great — but that’s because it took years. And I’m no better at break-ups. I haven’t gotten any stronger, I just try to learn my lesson in a way where I don’t have to re-learn it, and that’s the only thing I can do. It gets a little better every time I get out of a relationship, I know I’m never going to do that thing again. You and Will wrote this together, but the press notes tell us you two dated for a few weeks way back when. I assume you were able to be good friends after that? We were. We dated for three weeks and then he kind of dumped me. I was like, “Ugh, whatever.” Then we became friends a couple months later. He reminded me recently that he had apologized to me for not treating me well, and then we became friends. That’s nice! I think that was obviously an essential part that I had blocked out, but… so we were friends for a long time and talked about writing, and started things but never finished them. But the Celeste and Jesse relationship, that dynamic is very close to the one that Will and I have — except we don’t still have that “will they/won’t they” tension. We’re basically brother and sister now. So that’s what happens, huh? Well, listen — not with everybody! I have people with which that thing will never go away. That’s the crazy part about being an adult: when it’s like, [your feelings for another person] are never going to go away. But it doesn’t mean I should be with that person. I have somebody that I love and will always love, and we’re friends, but we’re never going to be together. That sucks, but you can’t always reward the connection with a lifelong relationship. Sometimes it is what it is. You’re so wise! Ugh, not really! [Laughs] There’s a line in the film that stuck with me: “Would you rather be right, or be happy?” That’s the kind of thing that really sucks to hear until you realize that it’s true. I know. To me, that was really the key to turning to adulthood for me. For so long when I was precocious and in my twenties I thought, “If I take right action, if I know what’s right, I’m going to be fine.” And then shit happens, because shit always happens to you. Then you have to learn how to be flexible and see grey and not hold onto a concept, or not fight for a mission that’s going to make you unhappy. For a long time I was convinced that I could will whatever I wanted to into being. Me too. My Will and I bring this up all the time — free will versus destiny — because I think when you feel like you have control over your life you do think, “Well, if I just do this, I’ll make it better.” Then you’re like, “Oh my god, maybe there is no free will, because things happen and if you try, you’re going to be miserable.” [Laughs] Well, you’ve given us all a lot to chew on. In terms of tackling the romantic dramedy genre, how did you and Will approach it, and what did you want to do differently than what had come before? The kinds of romantic comedies that I’ve always responded to, that I’m obsessed with, that I watch incessantly, are When Harry Met Sally… , Manhattan , Annie Hall , Broadcast News . And what I love about those films is that, yeah, maybe they’re hilarious, but they also have these rich insights and complicated relationships, and you walk away feeling something. You’re left with something. The humor comes out of the pain of the reality of the relationships. Mainstream film doesn’t have as much of that element anymore, so we kind of wanted to do something like that and hopefully touch upon some kind of socio-cultural trends that relate to people, that they feel haven’t been represented in movies. What are some of those trends? There are a couple of things: One is the Peter Pan-syndrome boy and the Type A woman relationship, and I think that has been touched upon — that’s, like, a Judd Apatow model. That’s his thing. But then more it’s growing up with somebody and feeling like they’re a family member, somebody that you loved, and trying to transition into friendship. Can you be friends with your ex? What does that actually look like? How do you get past a relationship that has defined you for so many years and try to keep some part of it but not throw all of it out, just because you’re not going to be together anymore? Right — and that would be the typical immediate reaction to most break-ups. To throw it all out? I think there’s some survivalist protection thing involved, too. I personally don’t think you can go right into being friends with somebody right after so long being together. You have to have a break. You have to heal, you know? [Laughs] People say this to me all the time and I fucking hate it, but you’re only ready when you’re ready. Chris Messina’s character says it in the movie and it’s so annoying, but you go back as many times as you need to go back before you’re done with that lesson. You’re going to do it until you’re not going to do it anymore. So true. Meanwhile, Celeste and Jesse also manages to feel very authentic to L.A. — not just the local landmarks and spots, but even something in Celeste’s constant plugged-in multimedia engagement. Maybe that’s something of the contemporary female experience, in an age when everyone’s consumed by email and the ego-driven Twitter mentality, all these things pulling you in different directions at the same time. For sure. Also, her job in the movie is to stay connected. And to be smarter than everyone else, in a way — to be able to forecast the future, to predict trends, which is exactly what she has trouble doing in her own life. Exactly. If we were being really simple and cliché one of the themes that we were going for was, she can predict everyone else’s future, but she can’t predict her own. She picked a job where she can always be right, and she can prove to herself that she’s always right. Then life happens and she can’t be right about it. Some of the more comic scenes — the awful date Celeste goes on at Chateau Marmont with the celebrity photographer, for instance — were those inspired by terrible dates in real life? That happened to me. No! It did not! It did ! Horrible, horrible dating story. The whole thing? The whole thing. Yeah. That’s amazing. Is it? [Laughs] It was less amazing when it happened, and then like six months later it was okay, I could tell the story. The worst part was that I had a friend that I told the story to and I knew that she had dated him briefly, and the same thing happened to her! He was, like, a serial masturbator. I want you to know that makes that scene so much better for me as a viewer. I know, it’s so sad. Also: Was Ke$ha not available to play the trashy pop starlet played by Emma Roberts? [Laughs] You know, there’s obviously a little bit of that in there but it’s another kind of composite. It’s her, a little early Britney Spears, a little Taylor Swift, a little Miley Cyrus… Sure, but there is a nod to the unexpected wisdom in that character. We didn’t want it to be this superficial, shallow girl. We tried a little bit to buck convention. Every character in the movie, we tried to do a thing where you expect one thing from them and they surprise you, which is hard to do. Next up for you is another re-team with Will, adapting your own project? Frenemy of the State, yeah. We’re doing an adaptation of a comic book that I co-wrote, for Universal and Imagine. It’s about a socialite who is recruited to be a spy in the C.I.A. Are you thinking of starring in it? No! It’s like a 20-year-old girl. I could be her mother. I could legitimately be her mother. If you were a teen mom, or something. Yeah, if I was a teen mom. So we’ll see. Hopefully they make it! Follow Jen Yamato on Twitter . Follow Movieline on Twitter .

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Rashida Jones on Celeste and Jesse Forever, Break-Ups, and The Worst Date Ever: ‘He Was A Serial Masturbator’