Refinery29.com — In a world full of rom-coms, when was the last time you cried over an onscreen breakup that actually stuck? No grand gestures to save the day, just pure, raw, lust and heartbreak. If you want to get so deep in your feels you forget if you’re actually heartbroken or just bleary-eyed over someone else’s love story, then you may need to subscribe to the church of Drake Doremus.

The director is known for his mostly improvised, chill-inducing romantic dramas (Like Crazy, Newness, Equals) and his latest is a tender-to-the-touch look at a modern love triangle in Endings, Beginnings, which premieres Sunday at Toronto Film Festival. Much like his previous work, Endings, Beginnings is clever and cutting, but also soft and quiet. Shailene Woodley is at the heart of the film playing Daphne, a thirty-something artist (her specialty is hand-painted tea pots, which she sells on Etsy) who recently and abruptly quit her job and ended her long-term relationship with her boyfriend (Matthew Gray Gubler, in his third Doremus film).

Looking for a hard reset on life, Daphne moves into the pool house of her much more together older half-sister. She also stops drinking, focuses on looking for a new job, and cuts men out of her life. Until, of course, she meets two men at a New Year’s Party. One’s brooding, asking her for a light of a cigarette in the most drunken and charming of ways. He’s wearing a shearling jacket, worn-in with adventures. The other’s in LA’s version of a suit — he’s put together, and looks at her with the steady intentness. Daphne should be avoiding both, but she quickly becomes enamored with bad boy Frank (Sebastian Stan), a nomad who drinks absinthe, and good boy Jack (Jamie Dornan), an academic who has a dog and dreams of moving to Europe. What starts as innocent text-flirting evolves into two full-blown relationships. Oh, and the guys are best friends.

When Stan first read for the film, he read for both Frank and Jack’s role, but what really attracted him to the heady rom-dram was Dormeus himself, of whom he’s been a huge fan. “I met him and I said, ‘I gotta tell you, I don’t know which one of these people you are seeing me as, but I really relate to both of them. I love both,’” he says over the phone to Refinery29. Stan’s in London where he’s filming the spy-thriller 355, a movie he says is “stylistically and tonally very different,” than Endings, Beginnings, but with “a couple of similarities here and there.”

“And we just got very deep. We got into relationships and being in our 30s and the world we are in right now, and all our experiences.” The vulnerability seen on-screen between Woodley, Stan, and Dornan is something special, and almost entirely improvised, based on just 80 pages of notes. Endings, Beginnings is a far cry from the big budget Marvel movies you’re used to seeing Stan in (he plays Captain America’s pal Bucky Barnes in seven Marvel movies and one upcoming spin-off series.)

It’s those real adult experiences and emotions that come through in the film, along with the clever text message visualizations that pop up between the three romantic leads, that make this film both timely and nostalgic. Ahead, Stan talks about the vulnerability of improv, being type-cast as a “bad boy,” and the weird, but totally plausible, idea of him appearing in the Gossip Girl reboot.

This interview contains mild spoilers for Endings, Beginnings.

I was reading your Instagram post earlier gushing about working on this film with Drake. When did you become a fan of his, and why did you two think Frank was the role for you? 

“I was aware of [Drake] for awhile. Like everyone else, I loved Like, Crazy, and then I also like his recent movie with Nicholas Hoult, Equals. I was also just really interested in doing a movie and improvising  —  because the entire movie is practically improvised. I never worked in that medium before. I got a call saying, Hey do you want to meet with Drake and talk about this movie [and] read the draft?, which was basically like 80 pages. There were two guy [parts] at the time. I met him and I said, ‘I gotta tell you, I don’t know which one of these people you are seeing me as, but I really relate to both of them. I love both.’ And we just got very deep. We got into relationships and being in our 30s and the world we are in right now, and all our experiences. Again, I didn’t really know that is where we were gonna go, but he was very honest with me and I was honest with him. We parted ways, and the next thing I knew he called me to have a session with somebody at the time that he was thinking of for the role as Daphne, and I went in and had a 3-hour improv session with him, then he called me and told me that he wants me to do the Frank role and I was fine with that.”

Only 80 pages. Everything else is improv? All the film’s dialogue?

“Yes, that is all literally on the day, in the moment, happening real-time. Basically, the script that he had was just the outline: Daphne comes out a recent relationship and moves in with her best friends. They’re having a New Years Party, and she runs into Frank who asks her for a cigarette. It was all outlines, but in terms of the dialogue and how we would get there, that was all improvised. That was an interesting experience because I had never worked that way and no take is ever the same. I walked away from that experience feeling very vulnerable. You’re not hiding behind any lines.”

The improvisation really added to the film. I left it feeling more emotional than I expected. 

“We’ve all had relationships, and we know how tricky they are. They’re complex and there’s many layers. I don’t know — I have always loved romantic comedies. I grew up on When Harry Met Sally and all that, but I sometimes feel that relationships aren’t entirely depicted as messy and as raw and as painful as they are. That’s why I loved working with him because I feel like he gets to the core of situations. I’m happy to hear you related to it because that is what he wants. He wants you to go, ‘I’ve had that conversation…been in that situation.’”

There’s been a resurgence in romantic comedies, but not so much romantic dramas like this. Do you think there’s a reason why?

“I love romantic comedies and there is a space for them, but [rom coms] are hopeful. Sometimes when I go to the movies, I don’t want to necessarily see what my life is. I want to be like, Hey! It’s nice to think that maybe that could be that way. If you want to be inspired, or laugh a little bit — there’s that element of it. And sometimes you want to see a movie that makes you feel less alone in your experience. A lot of European films are much closer to this, and I think Drake loves a lot of European films and is influenced by them and the personal quality. Structurally in romantic comedies, you have bigger things happening, right? Whereas [in this movie], there are big things happening, but there’s a much more subtle transition through everything.”

Frank is the “player” of the film, while Jack is the “good guy,” for lack of a better phrase. You’ve said before that you didn’t really know why you were often cast as the “bad boy.”  Do you still not know why?

“I don’t know! [Groans] I don’t know. The truth is, the reason I was saying [I could play] Jack was that I talk a lot in my life. I philosophize a lot. I try to read things. Then I think about it, and then I wanna talk about it. I relate to that [aspect of Jack]. And actually, there was a lot to Frank and Daphne that we shot that was funny. They had a lot of their own back and forth, but what ended up being in the movie —  I think Drake never forgot the vision that he had for Frank — [was him] being much darker than we shot. I am happy it ended up that way because there needed to be a contrast.

But I don’t know! I am glad they think I can do this. I am one of the most over-thinking, neurotic people I know. So I don’t know how it happens, but it keeps happening.”

I thought a big part of Frank also was his big shearling jacket. Since most of the movie was improvised, did you have anything to do with his outfits?

“Oh yeah, I kept that jacket, first of all. It’s a great jacket. What’s great about Drake is that he was like, ‘Hey, listen, people wear the same stuff all the time. If something works, let’s just it.’ I was like yeah, the guy probably kind of flies by the seat of his pants anyways so he just has a few things. I think I wore some of my own jeans. The boots I wore were mine. Drake definitely wanted us to wear our own stuff so we could feel comfortable in it.”

This was originally called No, No, No, Yes and ended as Endings, Beginnings. How did the title change shape the movie?

“It was always a working title. I saw that it was paired up with her experience — every no and every yes was paired to one of the relationships that she was going through. Endings, Beginnings is a little more specific. I know for awhile he was even contemplating a title that was even just made up of emojis which I thought would have been really fun.”

Oh yeah. I loved the texting aspect in this movie.

“There is an element of texting in the time period we are in, and there is this new language to it. They got it in the sense that both Jack and Frank have their very specific ways of texting. Jack probably uses punctuation, and Frank does not. [Laughs]”

You’ve worked with a few of the Big Little Lies women now. Do you have plans to work with the others like Zoe Kravitz, Reese Witherspoon, or Laura Dern?

“That has not hit me — that’s kinda funny. I don’t think I have ever met Reese Witherspoon and I’ve met Laura Dern. If the opportunity presents itself then great. I certainly wouldn’t have had a problem if there had been a role in the second season. I would have done it in a second. I loved the first season.”

I have one more that I have to ask about — obviously Gossip Girl is getting rebooted, and Chace [Crawford] said it made him feel “old,” but he’d be down. Have you thought about it at all? 

“[Laughs] I don’t even… it’s so weird. Somehow a lot of people talk to me about Gossip Girl, and I always thought I was just a guest star. It was a very special show. It certainly defined those years, and we all got our start there in a way. It would be hilarious and weird and crazy. He’s right — we are old! I don’t know what business they’d have with me, but, Jesus. If there was some funny little witty thing and they called and we’re like, ‘We’re doing this thing and we have everybody….’ I’m not gonna be the asshole that says no. Maybe I’ll be in the background scooping some ice cream.”