Photo by David Lanzenberg, Courtesy of Sony Pictures Classics.

From her long tenure as Jim’s (John Krasinski) girlfriend on “The Office,” to her now current starring role as Leslie Knope’s levelheaded best friend Ann Perkins on “Parks and Recreation,” Rashida Jones has quickly become one of the most sought-after actresses in Hollywood.

In between her stints on “The Office” and “Parks and Recreation,” she’s done a handful of feature films (mostly big budget comedies and the ilk), but her most recent film, “Celeste and Jesse Forever” — which she also co-wrote with Will McCormack — is her first passion project, and one that represents a change of pace for her career.

Jones stars opposite Andy Samberg – in a surprising dramatic turn – as a separated couple and lifelong best friends who just can’t seem to let go of each other.

It’s both a very funny film and a surprisingly emotional – and at times dark — take on marriage, going through divorce, and going through life changes when, frankly, that’s the last thing you want to do.

Meets Obsession sat down with Jones and co-writer and co-star Will McCormack just before it’s D.C. opening to discuss the excellent new film, the process of making the movie, and the often blurred line between ‘friendship’ and ‘romance.

MO: So how did you get the idea for the movie?

Rashida: We had a lot of friends who were in similar situations to this and, I guess, stole from their lives. You know, what good friends do [laughs].

We both had unhealthy relationships with long-term exes and it just felt like something we kept seeing. This type of guy and this type of girl — a guy who’s just sort of chill and not too interested in getting out there and pursuing his career, and a girl who’s sort of on top of it all; that sort of dynamic.

MO: How did you end up casting Andy Samberg? He’s usually known for more comedic roles and this was a lot more of a dramatic role than we’ve ever seen from him.

Rashida: I think Andy’s sort of had this inside him for a while. He said he wanted to do this and we were like “I don’t know…”

Will: Yeah, we sent him the script and we were like: “Can you do this?” and he was like “I got this.” We said, “No, really, can you?” Then we went to New York and we read with him and he was incredible.

Rashida: He really crushed it.

Rashida Jones as Celeste and Andy Samberg as Jesse. Photo by David Lanzenberg, Courtesy of Sony Pictures Classics.

Will: It was fun to watch because you were sort of watching an actor do this for the first time in his life; it was amazing.

MO: So, did you write the characters with particular actors in mind?

Rashida: A few of them…yes. The ones that we played. And we wrote that part for Chris Messina because he’s a close friend of ours we knew that he would just nail it, which he did.

Will: We wrote Celeste for her.

Rashida: [laughs] Yeah. But everyone else we sort of had a wish list, and we did pretty well with it.

MO [To Will]: Were you ever slated to play Jesse?

Will: No, well maybe originally when we first wrote the movie…

Rashida: Four years ago…

Will: [laughs] I read Jesse a lot in the beginning; I read a lot of characters, I even read Celeste a lot too.

Rashida: You would have made a good Celeste

Will: [laughs] I guess for a moment I was, but no, not really.

I’m a character actor, I always have been and that’s what I want to do when I act. I was really happy to play Skillz, that’s the part I wanted, and I was happy to get the part [laughs]. But I sort of feel like I’m older than that now, and Andy was perfect in the role.

Andy and Rashida have been friends for a long, long time so they already had a sort of built-in dynamic, little idiosyncrasies; a really great connection, so it seemed like a natural fit. And it felt fresh, since he had never done anything like this before.

MO: There seems to be a central theme in “Celeste and Jesse Forever” about the difficulties of letting each go. Was there ever a certain project or certain character that either of you had a hard time letting go of?

Rashida: [laughs] We have a thing called ‘Character Island’ where all of the characters that used to be in our movies or in our scripts get exiled to ‘Character Island’. There were some characters in “Celeste and Jesse” that didn’t make the cut. There was a little girl…

Will: Yeah, there was a little girl.

Rashida: There was a sister and a little girl…

Will: They got cut.

Rashida: Jesse had a sister and she had a daughter who was kind of a sagely little girl who sort of became Riley. She was supposed to be, like 6 years old. But I think we were both totally fine cutting her out of the script, right?

Will: [laughs] Yeah.

Rashida: We were ruthless about that…

Will: Wait, do you mean like characters we’ve played in other movies?

Andy Samberg as Jesse and Will McCormack as Skillz. Photo by David Lanzenberg, Courtesy of Sony Pictures Classics.

MO: Yeah, if there’s a certain character you’ve played that you’ve had a hard time letting go of…

Will: No, I’m usually so psyched when I’m done [laughs]. I’m like “I don’t have to come back tomorrow? We’re good? You’ve got it? Great…” I’m like that when I act too, “Good? We’ve got it? Great, moving on…” [laughs].

Rashida: With comedy, you don’t have to get in deep with a character that it becomes hard to let go. Although, I remember after finishing my one episode of “Freaks and Geeks,” I cried so hard. I was so upset…

Will: [laughs] Seriously?

Will: I’m barely in “Celeste in Jesse Forever,” but I wish there was more scenes with Skillz because it was fun to act with [Rashida]. It was particularly fun to watch Rashida because she was so locked in to the part, and for me — I’m biased — but it was watching a really good part and a great actress intersect, which was very exciting to watch. It was also emotional, because that part, you had to do a lot, and I’m sure you were exhausted but psyched.

Rashida: Afterwards I went to Asia and just, like, sat in white pajamas [laughs]. It was like a retreat I went by myself to Thailand and just sat in white pajamas for, like, a week [laughs].

MO: Sounds like you were really done with Celeste.

Rashida: I was so done.

Will: I just went to the mall [laughs].

MO: I’m curious to know about the writing process, specifically, when you were writing it, how much did you judge the characters as you wrote them, if at all?

Rashida: We were just talking about how in one of the early drafts, Will was like, “is Celeste too unlikeable? Are we just screwing ourselves because people won’t find a way in?” So we did some work to sort of soften her, but I don’t think you can judge your characters. We really tried to create a balance with all of our characters so nobody was villainous or reprehensible.

Will: I think it’s good to make your lead unlikeable as well, because as people we all have flaws. I feel like people can relate to a flawed protagonist, but we wanted to make sure you weren’t too unlikeable.

Rashida: Right, of course, and you were right — we did soften her. She’s still unlikeable, but then she gets hers, so you start to feel bad for her.

Will: We wanted to make it realistic in that people don’t change a lot, they change a little, which — in turn — is a lot.

Rashida: They change a little when they’re forced to change. All these things happen to her and then at the end of the movie she just doesn’t yell at somebody for a change. That’s all she did.

Andy Samberg As Jesse And Rashida Jones As Celeste
Andy Samberg as Jesse and Rashida Jones as Celeste. Photo by David Lanzenberg, Courtesy of Sony Pictures Classics.

MO: Rashida, your character makes a huge career mistake that ultimately works out for her, has that ever happened to either of you personally?

Will: Maybe our writing career?

Rashida: [laughs] This was a huge mistake.

Will: But look, it’s actually coming out!

Rashida: It would be so cool if it were true.

MO: Like a movie you didn’t get, but ultimately it led to better opportunities?

Rashida: Oh, that happens sometimes. There have definitely been some parts that I was torn up about not getting, and then I see the movie and I’m like “I’m good” [laughs].

I remember there was a movie I was up for and I thought it was going to change my career, and I was devastated when I didn’t get it. I don’t even think the movie ever came out.

Will: Or got made.

Rashida: [laughs] Or got made. I kind of believe that nothing’s really a mistake. I recently did that thing where you accidentally send an email to the wrong person.

But I feel like that’s never a mistake. Like, it was clearly something I needed to say to that person, and I didn’t even apologize, I just continued the conversation as if I meant to write it [laughs].

MO: Celeste and Jesse have a lot of hilarious idiosyncrasies with each other in the film — especially in their cringe-worthy couples speak, so I was curious what’s the silliest thing you’ve ever seen or heard a couple do or say.

Will: I don’t know, um, I was on vacation with some friends that were maybe slightly vapid and I heard a conversation that went like this:

“You’re so tan.”

“No, you’re so tan.”

“You’re so hot.”

“No, you’re so hot.”

And that was the entire conversation [laughs]. I was like, “I wonder if these should be my friends?” I mean, they were tan, and they were pretty hot.

MO: It was a truthful conversation.

Will: [laughs] It was pretty honest, like that to them was there reality. They were tan and hot.

Rashida: [laughs] I don’t know specifically, but I definitely have friends that I catch sometimes just speaking like a little bit higher to each other.

Will: Like baby talk.

Rashida: Yes, and I’m like, don’t do that…like ever, definitely not in public. But everyone does it anyways.

MO: I recently watched a similar film, “Friends with Kids,” and it seems like the idea of films that explores the often-blurred line between friendship and romance is becoming a trend — a sort of update on “When Harry Met Sally” — so I’d like to know, do you think it’s possible to still be friends with an ex?

Rashida: Ours is like a slightly different version because there’s the added complexity that they were married, so I feel like maybe our version is begging the question, can exes be friends?

MO: Exactly

Rashida: I feel like my answer is it depends: A) Were you friends to begin with? I’ve dated people that I shouldn’t have dated because I wouldn’t have been friends with them in the first place.

And B) You need to leave a little time for healing. I don’t think you can go right into being friends with someone you just broke up with.

Will: “Without recognition there can be no healing”. – Sinead O’Connor.

Rashida: [laughs] Or Biggie Smalls.

Will: I think they can. I’m friends with most of my exes because I’m sort of proud of my ex list, I’ve dated some really great girls…

Rashida: But with time…

Will: Right, with time. I think the interesting thing about our movie — I hope — is that they’re hasty; they sort of try to be friends without doing the necessary emotional work that needs to be done after a break-up. Celeste doesn’t even think she needs any, and I think that’s why her descent is funny, because she’s like “Oh my god, I have to do feelings?” No one’s exempt from that, you have to go through it. So, I think you can, but I think you need to communicate first.

MO: You mentioned earlier that you went through and picked all these actors for the film, so I was curious what sort of process did you go through to pick a director? Also, what was he trying to achieve with all this gorgeous cinematography? It was one of the best looking romantic comedies I’ve ever seen.

Will: Made for under a million dollars, $840,000 actually. David Lanzenberg [ed. note: the film’s cinematographer], he’s a genius.

Rashida: He’s the jam, he’s so good, and he’s never done a feature film before.

But anyways, we saw “The Vicious Kind,” Lee Krieger’s last movie, which is a fantastic film. If you haven’t seen it, definitely see it, it’s very different tonally from our movie. It’s a dark family drama with Adam Scott and J.K. Simmons, and the performances are so good and it looks fantastic.

So we met with Lee and he’s so charming, so smart, and so talented and immediately got the movie. He’s 28, so he’s of the generation who gets it and had been through some similar morphing himself. He’s also this refined aesthete and has this fine taste.

Will: I was obsessed with “The Vicious Kind,” I was like “Oh my God, this is one of the best indie films I’ve seen.” We weren’t looking for like a big comedy director, we were looking for a dramatic director because we wanted that part of the movie to be excavated. He was talking about the movie in terms of films like “Husbands and Wives,” “Annie Hall,” and “Broadcast News,” and we were like “Yes! That’s it!” He really tonally wanted it to have heft, and so did we.

Rashida: He’s very sensitive and a good communicator on set, and he’s great with actors, and knows how to make the scenes about the emotions — that was something that was important to us. Between Will, Andy, and I, we had the comedy stuff covered, we didn’t need to force anyone to be funnier than they already naturally were.

MO: There’s a great line in the film that goes something like, “You have to crawl before you can walk.” As actors and writers you’re always growing with each experience, but is there one movie or project you’ve done where you’ve felt that big transition?

Rashida: That’s a good question.

Will: Prior to this? This was the biggest growth spurt of my life.

Rashida: It was huge for me too; as an actress, as a writer, as a producer, as everything.

Will: This was professionally and personally the hardest thing I’ve ever done, but also the most gratifying

Rashida: Me too.

Will: It’s really intense to write, produce, and make a movie, and have it come out in the world. It’s a very vulnerable thing, and we tried to write a comedy about heartbreak to the best of our ability. We weren’t trying to be cynical or satirical at all in the emotional parts of the movie. It doesn’t take guts to do that, but it does take some measure of vulnerability, and this is how we felt it; this is how we put it out into the world.

As an actor I’ve never really had a lot of fear, but as a writer I’ve had a ton of fear about exposing myself. It was great to go through the process, and I would do it again, but it was hard; I had a lot of fear about it. This movie, for me, by far is the hardest thing I’ve ever had to do.

Rashida: Same. As an actress I’ve never had to carry anything before, and we wrote this part that was challenging; to be likeable and have some levity, but also to have some gravity, it was a tough balance — and I was in it. I was feeling every emotion in a way that I don’t really like to feel emotion, because they’re scary [laughs]. So it was challenging, but great.