SS: Okay, so first thing’s first. How are we going to get The Mighty Flynn made? From what you know, what’s keeping it from being produced?
LS: Thanks for keeping it alive for me, Carson! I think I'm ready to cast it out again and see if it gets any actor interest. When “Up In The Air” was made, it felt like I had to put the story of an efficiency expert to bed, but now that some time has passed, and honestly thanks to your vote of confidence, I’ve come up with a few potential ways to make it new and interesting. One possibility is changing the time period, which could work thematically while also allowing me to keep devices like the phone book and resumes at Kinko's without feeling dated. Also, the relationship between Flynn and Boaty is one I’ve been trying to tell for a long time, so I found myself naturally drawing from it for Dodge and Penny in “Seeking a Friend”. I like a male character who's anything but a man-child and then prying him open with the help of a free spirit who's anything but type-A. It's basic storytelling, I guess, but it's actually personal for me. As long as it feels different, I'll pursue it. You'll have to help me fix the ending!
SS: Do you need me to call anyone?
LS: Please call Jason Reitman in 2008 and ask him to make Juno 2 instead.
SS: Could you tell us a little about your emergence as a screenwriter? How many scripts had you written before you got your first job?
LS: I was always in love with plays and movies, so I started writing psuedo-screenplays when I was a kid. I still have many of them, including "Ripple", a romantic dramedy about dying dolphins, "starring Lorene Scafaria and Ethan Hawke". With those delusions of grandeur, anything was possible. I wrote a few plays, put up my first in the greater New Jersey area, and eventually put up a relationship play in New York called "That Guy And Others Like Him". I was answering phones at a film company, doing an embarrassing amount of extra work, and decided to adapt the play into my first true screenplay. I wrote two other scripts, then started looking for an agent and moved to LA. Five scripts deep, I teamed up with my then-roommate on a children’s adventure called “Legend Has It”. It wound up being optioned by Revolution Studios so that was technically my first job. Two years later, I wrote “The Mighty Flynn”, which was number eight, and got it set up at Warner Independent. I was basically hired off of that to adapt “Nick and Norah’s Infinite Playlist” and that was the beginning.
SS: Was that first job how you got your agent?
LS: When I first moved to LA, I was talking to a smattering of agents who never called me back. My very very first agent came from sending a query letter, so I still believe that a well-written, well-intentioned letter is a good way to reach out, especially in this era of accessibility. I looked up which agents sold scripts from first-time writers. She said she liked my letter and the title of my script and asked to read it. She later sent me a rejection letter and then called a few days after that to say forget it and could she read anything else. I sent her my other two scripts and she suggested I move to LA. She almost immediately switched agencies and I got lost in the shuffle. My old writing partner and I were working with an agent-in-training who helped set up "Legend Has It", so he became our first official agent and we became his first clients. I changed agencies a few years later and have been at the same place since.
SS: Looking back at those first (paid) experiences in the business, what did you learn from them? What kind of mistakes were you making as a screenwriter then that you’d never make today?
LS: I’m sure I’ll continue to make the same mistakes. I'm lucky in that I've had a variety of different experiences, from writing on spec and pitching original ideas, to adapting a novel or real life story or an all-too familiar musical. I've also failed at selling pitches and been fired and rewritten. I've spread myself too thin. I've quit. So hopefully I've learned from those larger mistakes. I try to work with people I like and I try not to get involved in anything unless I think I'm the right person for the job.
SS: What would you say is the hardest thing about screenwriting for you now? Why do you struggle with it and what do you do to conquer it?
LS: I struggle with feeling burnt out and uninspired. Even though I only have a few produced scripts, I feel like I've been writing a long time. Sometimes it's hard to live in LA. The same things that make it great can also make it feel overwhelming. Thinking as a director now, it's harder to write a first draft freely, beginning to end, warts and all, and then give myself the space to fix stuff in later drafts. I find myself rewriting as I go, which can be helpful, but slower. Now I struggle with "what's next". I feel like I threw the kitchen sink at "Seeking A Friend". It explores so many of the themes that swim in my head, and the high concept made it easier to write character-driven scenes within set-pieces. Point is, I'm in my head too much and should probably get some fresh air.
SS: I really love your characters. Especially the ones in Mighty Flynn. Everybody’s so unique. How do you build your characters?
LS: Thanks for saying so! I went through a phase of thinking in terms of a character's job, like in "Mighty Flynn". I like exploring someone's psychology and thinking of what kind of person would do this for a living... what could be in that person's history and how that could reflect the themes I was interested in expressing. That script sparked "Man and Wife", again exploring an immigration officer and what a job does to a man when he is "the man". For both of the male characters, as well as Dodge in "Seeking A Friend", I was exploring a specific archetype; men who are in need of an awakening. For Flynn, he was a fairly heartless bastard who only moved an inch, but all that he needed to go through to get that far. I've always been interested in people and relationships, psychology and sociology, how people react to different scenarios. In the case of "Seeking A Friend", I thought about everyone facing their own mortality differently, and then came up with the various characters to best articulate that. I think it helps that I look at myself with a critical eye and I look at the people around me with a sympathetic one, so I try to love every character but also know what they're doing wrong.
SS: What about dialogue? What would you say are the 2 or 3 things you focus on most when writing dialogue? What’s most important in getting it right?
LS: Write how people talk.
Not everyone talks the same.
Keep it specific.
SS: I notice you have a lot of setups and payoffs in your script. My guess is that this means you outline a lot. Do you think outlining is important and what’s your process?
LS: I don’t like to outline that much. I usually prefer to write a first act without outlining so that the characters feel and sound a little more authentic before making major plot decisions. I think then if you write something specific in your first act, it becomes a natural setup, and something you can follow through the script. If those specific things can relate to the theme or the journey that the character goes on, it becomes easier to set it up and pay it off, without feeling like a forced characteristic. In "Man and Wife" I remember the traveling orange was something that became a set up and pay off. In "Seeking A Friend", the harmonica took on meaning as I went along.
SS: One of the most difficult sections of a screenplay for young writers is the second act. Can you give us any secrets about how to dominate the second act?
LS: I still battle with the second act and I suppose it varies for different genres. I think it's easier if you break it up as much as possible. I like to think of the page numbers like the minutes on a clock and at every ten to fifteen minute mark, something should change, so the second act has three major shifts to go through... 30-45, 45-60, 60-75... I think those are the points to present conflict and tension so that something changes in your characters. It has to constantly build and unbuild and build again. It should have a big page 60 high and a page 75 drop. I think it has the shape of an EKG or a really good roller coaster or even a song. If a song goes verse, chorus, verse, chorus, bridge, chorus... or something like that... you can sort of see the shape of a screenplay.
If on page 30, your main character has a mission, like Dodge going in search of his ex, then your second act has direction. Then he's tested, facing various highs and lows, obstacles along the way. Even though I tried to mix it up in terms of genre-bending and surprising moments, it's actually a very straight forward structure. I remember hearing a complaint that "Nick and Norah's" didn't have enough of a ticking clock, so I was sure to give it a huge ticking clock.
SS: Lots of beginning screenwriters focus on getting a script purchased. Lots of purchased screenwriters focus on getting a script made. In your experience, what’s the difference between a script that’s good enough to get bought and a script that’s good enough to get produced?
LS: That’s an amazing question. I really couldn't tell the difference for a long time, but when I look back at old scripts, I can see how things got ignored. I still think it's important to write what's in your head, because even if it doesn't get produced, it could end up being your best sample of your voice. Even though I liked exploring characters, it took a long time for me to figure out structure. I still grapple with it. A book called "The Writer's Journey" and a very patient Dana Fox taught me some phrases and tricks. I still resist convention between the second and third act, which accounts for the change in pace in "Nick and Norah's" as well as "Seeking A Friend.” I think it's most important to concentrate on theme and tone. Those will make your story distinct and reveal the "trailer moments" of your script. After that, I think pacing is key. Hearing a script out loud is a good indicator of its possibilities.
SS: Can you give us a couple of “aha” moments in your career– those classic moments where you’re writing and some unforeseen force shoots into you and you realize what you were doing wrong all this time and understand screenwriting so much better now?
LS: The biggest "aha" I can think of was when I was working on the third draft of "Seeking A Friend". Even though I was thinking of it as an end-of-the-world romantic comedy, I still wasn't taking the two genres and colliding them within the scenes themselves. That's when I realized that the riot scene needed to be a break-up scene, and that the scene at Friendsy's is a date / is an orgy. I realized that at all times, the genres needed to be working for each other, and against each other, and it definitely outlined the larger set pieces and propelled the second act.
SS: A lot of writers say their perspective on writing totally changes once they direct a movie. Now that you’ve directed a film, are you joining the chorus? How did your perspective change, if at all? What did you learn?
LS: My perspective definitely changed. But it doesn't make it any easier. I always knew that editing was another form of rewriting, but I never realized how much so. There definitely was the script I wrote, the movie we shot, and the story we edited. I wish I had had the foresight to know which scenes we would later cut but we needed to see it all together, with an audience, to know what was affecting the tone in the wrong way. I ended up cutting a few scenes in the first act to make it a more streamlined story about relationships. A few amazing actors were cut out of the film, but it was for the benefit of the larger story. A couple scenes in the third act also were lifted to give it a stronger final push for Dodge and Penny. I definitely learned that sometimes less is more, that something can be done with a look. Not everything needs to be said. I'm going to try to apply this lesson to life.
SS: Knowing what you know now, would you have done anything differently as a young screenwriter in order to break in faster?
LS: I think I was lucky in breaking in fairly quickly as a screenwriter, but because I wanted to be a filmmaker, I wish I had the nerve and capacity and overall wunderkind-ness someone like Lena Dunham had to make a film like "Tiny Furniture" at such a young age. I had a real breaking point six months before "Seeking A Friend" got going. I remember threatening my agent that I was going to start auditioning for indies and pilots, as if this would prove more successful, because I was tired of being a hired hand, or seeing a project through many years and various iterations and only have it fall apart. I was tired of everything being on paper, so I guess I wish I wrote and directed a feature, no matter how small, a long time ago. But I think sometimes you have to reach a breaking point in order to figure out what you really want. Such is life.
SS: And finally, do you have any future romantic comedies planned about a female screenwriter who meets and falls for a really awesome screenwriting blogger?
LS: Boy reads girl. Girl reads boy. Girl does interview for boy and only hopes she didn't blow it.