For Lucy Hale & Nat Wolff, What Started With a Tweet Led to a Rom-Com

[Editor’s note: The following contains some spoilers for Which Brings Me to You.]

The Big Picture

• ‘Which Brings Me to You’ has a unique story structure with flashbacks and candid confessions that sets it apart from typical romantic comedies.
• Both Lucy Hale and Nat Wolff were drawn to the script’s generosity and warm-heartedness during such a dark time in human history.
• The on-screen chemistry between the two actors was enhanced by their involvement in the script, improvisation, and shared sense of humor.

In the romantic dramedy Which Brings Me to You, Jane (Lucy Hale) and Will (Nat Wolff) have a chance meeting that leads to them spilling their relationship guts over the next 24 hours. As they share honest recounts of the past loves and heartbreaks that shaped them, bearing their flaws and messy histories bonds them in a way that feels like it could be the real thing, if they decide to take the chance on each other.

During this interview with Collider, co-stars Hale and Wolff talked about the appeal of doing a different kind of romantic comedy, their determination to work with each other, wanting to tell a warm-hearted story at a dark time, what led Hale to tweet about Wolff 10 years ago, how they were able to bring some personal touches into their characters, the scenes that stood out the most to them, getting to sing a duet together, whether they think their characters relationship lasted beyond the end of the film, and which projects they’ve got lined up next.

Lucy Hale Says It Was the Relationship Flashbacks That Drew Her to ‘What Brings Me to You’

Collider: Because this isn’t your typical romantic comedy and the story structure is quite unique, when you read the script, what was the first thing that caught your attention and made you see this was something a bit different and made you want to keep reading?

LUCY HALE: For me, it was those flashbacks. We actually got to live out the backstory that usually is just exposition within the story. And I thought the dialogue was very quick and smart. It felt real and it felt grounded. But the element of living out these love stories with each other was what hooked me initially.

NAT WOLFF: I just saw an email that said, “Lucy Hale,” and I said, “Sign me up.”

HALE: Exactly. That’s exactly how it happened, let me tell you.

Nat, we often hear about how guys get dragged to romantic comedies, but is it the same thing with reading a script for one? Do you go into reading it thinking, “Oh, God, what is this going to be?,” until you realize that it is something different?

WOLFF: Yes, actually, in a great way I think. In the last 10 years, I feel like I haven’t done any project where I haven’t been killed or killed somebody. And in such a dark time in human history, I actually felt really excited about being involved with something that was so generous-spirited and warm. At the same time, I think it’s good for any couple, or people who are falling in love, to examine their past relationships and their past selves in order to have a pure relationship in the future. And then, honestly, I’ve been dying to work with Lucy, especially in a movie like this. I think she’s incredible. We’ve wanted to work together forever, so it was a no-brainer.

HALE: For me, I had worked with the director, Peter [Hutchings] before, on a film called The Hating Game, so I was excited about the chance of working with him again. You get scripts sent to you that are in this genre and there’s a formula for these types of movies. This one threw me from the very beginning, so that’s why I wanted to be a part of it. And then, obviously, I wanted to work with the great Mr. Wolff.

WOLFF: I’ve been offered so many stupid romantic comedies that are just like all the exact other ones that you always see. Whereas this one still has the warm-hearted accessible feeling, but there’s also something interesting going on.

HALE: It feels more human than a lot of rom-coms. When we get to live out these flashbacks, we see that Jane and Will are hopeless romantics. They do want something real and sustainable, but they’re damaged by the idea of romance and love.

Lucy Hale Planted the Idea of Working with Nat Wolff With a Tweet 10 Years Ago

Lucy, you recently did an interview promoting this movie where you talked about having tweeted about Nat in 2014. When you do something like that, was it just a throwaway comment, or were you hoping it might lead to working today at some point?

HALE: It was 10 years ago. The story behind that is we had met earlier that night at an award show and it was late in the night. I don’t know why I was tweeting. I don’t know what I thought was gonna happen. But I guess I did plant the idea in the ether of Nat Wolff and I working with each other, 10 years later. We’d seen each other around town a little. I worked with Nat’s brother [Alex Wolff] on something. We were due our time to create something. I think that’s exactly why Nat wanted to do the movie. He goes, “You know what? I think she tweeted about me 10 years ago and said I was the cutest. So, I think that’s why I should be a part of this movie.”

WOLFF: She didn’t say that I was the cutest. She said I might be.

HALE: Might be, and the verdict is still that Nat Wolff might be the cutest.

WOLFF: But I’ll go on record and say that Lucy Hale is the cutest.

HALE: You get some good points in my book.

How close is the finished film that we see now to what you guys first read? Changes often get made whether it’s during shooting or during editing. Were any major changes made or was it always pretty close to what you read?

WOLFF: Peter let us be involved in the script very early on. It was a beautiful script, but we got to make it much more personal and bring in things from our past relationships and our lives. And then, we also did a lot of improvising, Lucy and me. That’s actually a lot that’s different. There’s a freshness to it that I think came from me, Lucy and Peter being on the same page, but he also let us off the leash.

HALE: Also, in the original draft of the script, we still had the flashbacks, but our characters didn’t intercept the flashbacks like we do in the movie. That was probably decided pretty last minute, to keep their love story alive. I think that’s what really makes everything more seamless, having that love story stay alive within all the other love stories.

Does it also feel like it really helps with chemistry when you get to be more involved and you do get to make the characters more personal?

HALE: Oh, yeah, definitely. A lot of the time with these movies, you meet someone three days before. Peter thought it would be a great idea that the first scene we shot was the coat closet, which ultimately worked because that is right when the characters are meeting as well. I had a sense of who Nat was and how he worked. I was very familiar with how talented he is. It’s just one of those situations where Nat and I are very similar in a lot of ways and it was very easy to have chemistry with him.

WOLFF: Lucy could have chemistry with a wall.

HALE: Is that a compliment?

WOLFF: Yeah, it’s a compliment. You’re so good that you could have chemistry with anybody.

HALE: Also, when you meet people who get it, with Nat and I, it was very seamless. We have a similar sense of humor and getting to have these creative conversations beforehand established a foundation of respect and trust from the get-go. Once we had that, it made it very easy.

Nat Wolff Had an Awkward Sex Scene in ‘Which Brings Me to You’ That Lucy Hale Had to Watch

Because it is so unusual to have this thread throughout where you get to explore these past relationships, did you have a favorite moment from the different ages and relationships for your characters?

WOLFF: Honestly, my favorite was probably playing the age that met Lucy in real time, only because it’s closer to my age in real life and I felt like that was really exciting and revealing and scary to play somebody that’s at the same life stage as you. I loved doing that. But then, also, with the flashbacks, you got to go in a time machine and delve into these past selves and things that I hadn’t explored in a while, and that was really exciting. I also loved getting to enter each other’s flashbacks, but sometimes it was so uncomfortable. I had to do a sex scene and Lucy was just in the corner. A sex scene is already awful enough, and then Lucy was like, “Hey, sorry guys.”

HALE: I loved that moment. I don’t know about you, but I loved the discomfort of it all.

WOLFF: That’s a lie. She did not love it.

HALE: I loved that moment. I’m 34, and I never thought I’d be playing a teenager again, but it somehow worked. I loved playing all the different ages, especially the Catholic school girl. That was just so ridiculous. I don’t even know how a 16-year-old acts anymore, but that was fun. We wanted each relationship to feel a little different.

Lucy, your character is very direct with expressing what she wants. What was that like to play? Is that an aspect of her that you enjoyed? Is that a quality that you have or is that something that you find hard to access in yourself?

HALE: I feel like it’s a quality I have embodied recently. The last couple of years, I’m much more comfortable being direct about what I expect from people. I think Jane is a little too aggressive. When she says, “I wanna have sex with you in the coat closet,” I don’t imagine myself ever being that direct, but it is a quality that I do admire in people. It is something that I respect and that I did love about Jane. I think that’s something, throughout the flashbacks, that she learns.

There’s that fun moment in this where you guys get a little duet together with “It Had to Be You,” which leads to a kiss between the characters. What was it like to shoot a dreamy romantic comedy moment like that?

HALE: We shot that at a really famous bar in New Jersey.

WOLFF: It’s a really beautiful venue and we got to do this romantic kiss. I loved getting to lift Lucy up and turn her around. It felt like I was in a movie.

HALE: It felt very dreamlike and whimsical when we were filming it. The music element was a last-minute thing.

WOLFF: “It Had to Be You” is a famous rom-com song that was in Annie Hall and then When Harry Met Sally. It’s a romantic comedy tradition.

HALE: Having us both be a part of that was a last-minute decision. Peter texted us and went, “I have a crazy idea. What do you think?” And initially, I was like, “No.” But then, I thought, “What a cool risk to take?” Ultimately, it works because we’re already intercepting each other’s flashbacks. Hopefully, it’s seamless.

I’m someone who always wonders if the romantic comedy characters would stay together after the movie ends. When you play characters in these types of movies, do you think about that? Do you feel satisfied that you’re leaving the characters in a place where they’ll just go on living their lives together or do you think they’ll break up again?

WOLFF: We’re in the process of making Which Brings Me to Two. No. Even if they don’t end up being together for life, they are approaching a relationship in a more mature place than they ever have approached a relationship before. It’s a big growth. But I like that you don’t really know if they’re gonna be together forever.

HALE: Will even says something like, “We don’t have to decide right now. We don’t have to decide if we’re gonna be together. Let’s just keep talking, at least for today.” I think that’s a really healthy mindset. But I believe, in my version of the continuation of the story, that they’re still together. I think they’re in a really healthy place. It’s very evolved what they did with each other. I think they’re still together.

WOLFF: I think Jane murdered Will in cold blood. No. I think they’ll end up together forever. I think they have seven kids. They have way too many kids and now they’re just like, “Oh, my God, how do we make enough money?” That’s a whole other movie to be made that’s like Cheaper by the Dozen.

Do you guys each know what you’re going to be shooting next?

WOLFF: Yeah, I’m doing two things. I can’t really say what they are, but I get to do these really exciting supporting parts in these movies with some bigger casts and a music element that I’m really excited about. I’m going on tour for six dates, starting on [January 22nd]. And Alex Ross Perry made a movie, called Range Life, about Pavement, and I’m playing one of the guys in Pavement. That’s coming out soon.

HALE: I shot a movie over the summer, called Fuck Marry Kill, which will not end up being called Fuck Marry Kill. It will probably be F Marry Kill. That was really fun. It’s a Lionsgate movie that I think is coming out in the summer. And then, I have two things I’ve been developing for like a year, that I’m excited about. It’s flexing creative muscles in a different way.

Which Brings Me to You is in theaters. Check out the trailer:

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