Danielle

Today, I am super excited to have Pilar Alessandra with me. I first came across Pilar’s work through her fantastic podcast On the Page, which is just such a warm, fun space full of really practical writing advice that is just a lovely part of my week, and I’m super grateful for it. And I also then went on to read Pilar’s books, The Coffee Break Screenwriter, and also The Coffee Break Screenwriter Breaks the Rules, which I’m holding up for those of you who are watching on video, which again, is super fun, super practical, highly recommend.

So I’m really looking forward to talking to you about craft and all things comedy today, Pilar. But before we dive in, is there anything else you’d love people to know about you and your work?

Pilar

I guess that I am a teacher, that I do lots of classes on Zoom and in person. I’ve had the pleasure of travelling around the world, training writers at schools and film festivals. So..I think probably among all those things, as much as I love the podcast and I enjoyed writing my books, teaching is my absolute number one. So I would want people to know that.

Danielle

Yeah. And I think that really comes through in the podcast that you’ve just got such a lovely way of sharing those perspectives and really supporting and helping people in the way that you’d want a very best teacher to. And I also read about you that you’ve read two scripts a day for 20 years, which also gives you such phenomenal insight. I’m really looking forward to having that perspective.

Pilar

At this point, I consult a little bit differently. So I actually have five clients a day where they’re spreading out their script over four to five sessions. But yeah, it really comes out to the same thing. It’s a lot of scripts. It’s a lot of content, but it’s also like the coolest job because, you know, imagine if you got to binge-watch for a living or just watch an episode of your favourite TV show for a living. That’s kind of the work that I do, only on paper.

Danielle

Yeah. Which is wonderful. And again, gives you just such a great perspective of seeing different patterns. And I think that’s also why a lot of the advice that you give is so practical and so useful. So I’m going to pull out some different things today for people who haven’t had the benefit necessarily of that advice, or so we can put it all in one place here.

And where I’d love to start is with characters. I really loved in the Coffee Break Screenwriter Breaks the Rules, that you brought up the rule and then also the discussion of breaking it with regards to characters being likeable or unlikable and had your own terminology around that. And I wondered if you’d speak a little bit more to it. And I can confess a bit of a vested interest here, which is that I’m really interested in young adult fiction too. That’s what I’m writing in comedy. And there are some really interesting discussions sometimes, particularly around female teen protagonists or non-binary protagonists around likeability and unlikeability. And I found how you dug into that really helpful. Could you speak a little bit to them?

Pilar

I found it a really annoying note for so many years that my clients would work really hard at humanizing their characters and then inevitably get the, I don’t like her and it was usually a her. The judgments that we were doing for so many years on female characters and what makes a female character likeable to the rest of the world. I would say I do feel like that’s easing up. Thank goodness that people are. And you know what made it ease up? It’s the amount of content. For years, my feeling was…of course you want your female character to be likeable when she’s the only one you’re going to see in the movies that season or on TV.

You know, now we have a glut of female characters in all of their imperfections. So it’s become more normal for us to go, oh, a human being is on screen. I’m interested in what makes them human. Therefore it doesn’t always have to be a positive quality. I understand that I will get all the shades of that human, that humanness if you will, that humanity, and I will eventually come to empathize with the characters. And that to me is what you’re really going for. You’re going for empathy. You’re not going for likability. We often empathize with the least overtly likeable characters by relating to their situation. When a bigger jerk comes along and does something to them, when something’s exhausting them, when they’re being frustrated, sometimes we’re that jerk and we realise, oh yeah, I empathize with that person even if I wouldn’t necessarily hang out with them or don’t think that they’re making a positive choice. That was a very rambling answer to your question but I hope you got to an answer there somewhere.

Danielle

Yeah, no, totally. That wasn’t rambling at all. And like you say, that empathy being key is such an interesting point. And also in the book, you mentioned that relatability, which I think is akin to, because we don’t always act, well, no one acts perfectly. I certainly don’t. So like you say, being able to empathize for those things. I think that’s wonderful. And I’m interested, because you have got such a great view of all the scripts that you read and so many of them, and you mentioned things changing in relation to women and comedy and tropes. Are there any that still drive you mad, or that you wish could be dealt with differently within the industry, or where you think there’s still much space for development?

Pilar

I’m, well, it’s not that they drive me mad. It’s just that sometimes people lack imagination. And the first thing that they do with a female character is make their stakes a child immediately. And it’s funny, like, you know, with a man, that’s not exactly the first thing. It’s always sort of like, how are they going to balance being a mother and working? Like, it’s still a thing. Now, as somebody who balances being a mother and working, I get it. But I also think that there are women out there where, you know, their relationship with a child is not what defines them. There are many people who don’t have children. And to always look at women as child bearers or child nurturers, it’s part of what of a lot of females experience, but it’s not every female experience. So I would like to see people stretch a little bit more in terms of how they’re seeing women on screen that way.

Danielle

That’s super interesting. I’ve never thought about that before. And for example, I don’t have children. I’ve worked with young people in lots of different situations. And I find that particularly working with teens is super interesting and fascinating, but I’m not a mother. So yeah, I think that that’s a really interesting example. And I’m sure there are many, many more. That’s super interesting.

And I’m also curious then whether – because I had a really interesting conversation with one of my previous guests, Zanandi Botes, about different tropes in comedy and women’s roles and professions – if there are any professions that you feel like you see overused. Or situations or settings.

Pilar

Yes. And you know, it’s not just for women. It’s something, you know, if you watched…if we’re learning about the world only through movies, you would think that the only jobs people have are cops, special forces, and strippers. That we really enjoyed watching that woman on a pole who’s dancing to support her child and all that. And again, there is value in that, but it is not the only job, nor are cops the only job or special forces the only job for just a range of characters. So I love when I’m working with a client and saying, let’s start with an interesting job that we haven’t seen on screen before. What do you do for a living? And they’ll be like, oh no, what I do is really boring. No, it isn’t. You know, I’ll be able to say to them, what’s the worst, weirdest, funniest, oddest thing that would happen at work if you let it happen? What’s your worst-case scenario? And often they will, they will hit me with something that is really movie worthy. So it’s actually a great place to start… with a job we haven’t seen on screen before, maybe even your job, and then take that to the extreme. You could have something wildly original.

So in answer to your question, what jobs? Every job. We haven’t scratched the surface with what people do. And I would really love to see that on screen.

Danielle

Yeah, that’s wonderful advice. And like you say so much to really dig into and explore from our own lived experience. And that’s the advice again that I hear you mention on the podcast a lot too. And I think sometimes we rule it off as normal or boring or we’re so used to it that we undervalue some of those elements that could really bring life to a script.

Pilar

Absolutely.

Danielle

And that links a little bit in my head to to the Coffee Break Screen Breaks the Rules. You talk about writing what you know and breaking that rule too. So I know it sounds like it’s in contradiction to what you just said, but I don’t think it is in the sense that I love how you go into… things that you’ve learned, or that could happen, or what scares, or thrills you. So I wondered if you could speak a little bit to that and what you were thinking when you dug into that.

Pilar

Absolutely. It starts with what you just said, right? Of course, you’re always grounded with your perspective, right? But the what ifs, the going as far as you want, because if you only wrote what you knew, you wouldn’t be writing about things in space, right? So it’s the idea of you can still have a…what if somebody like you ended up in space? So there’s always a little tether to who you are and what you know and what your experience is.

But the whole, write what you know, thing, you know, come on, you, and use your imagination, go wherever you want. Now I think it’s different when you’re trying to capture somebody’s very specific ethnic, gender, race experience and going, well, I’m going to write that experience. I think in that case, there is the idea that maybe you should come at that with…,let’s say you still want to go for a historical character, okay, that is a different race than yours. Yes, of course, right? You’re going to come from, you’re going to say, this is an important story to tell. And my way in to tell it is this way. And I’m connected to it this way thematically, right?

in that case, you know, sort of speaking for everyone in a certain culture that maybe you’re not that connected to, sometimes that can get a little problematic. And in that case, you want to write from what you know, okay, with your way in being respectful of that other culture. But again, that story needs to be told. So stretch, stretch, stretch, and be tethered a little bit to your own perspective, if that makes sense.

Danielle

It does. It explains it really, really clearly. I love that. And I’m curious, when you’re teaching, and as you mentioned, you are such a great teacher, you run so many brilliant courses. Are there any particular shows that you find yourself going back to with regards to comedies, to use as examples? And if so, why do you pick those particular shows?

Pilar

Um, let’s see, well, in my feature class, I use an example from Booksmart. And I use that, I use a first scene where we get to know all of the characters all at once, because we get to know them through like tropes and archetypes. And then we break those things down over the course of the movie. And I think it does it brilliantly. And I also think it does it for young people in a way that feels real and contemporary. And it’s good for me to show some of my students who might not be young people, like, yeah, the world is not John Hughes anymore, you know? There are so many nuances to the way that young people are right now. So it’s entertaining, it’s informative, it talks about character and it talks about establishing and ultimately breaking the character’s own rules. So that’s one of the comedy examples that I use and feature.

In my rewrite class, I use a trailer from Bridesmaids because I like to talk about set pieces. And set piece is how you take a setting, how you turn a setting into an experience. And if you look at Bridesmaids, which is solely about like just, you know, bridal events that if you’ve ever been a bridesmaid, you have to do, right? So how do you make that interesting? They took every setting for a bridal event and turned it into an experience. So that’s another one that I show. Um, I love, I love showing comedy clips.

Danielle

Yeah, that’s lovely. I love that. And I listened to your recent episode with Rita, your daughter too, and there’s a really great discussion about Booksmart in there. So I’ll put that in the show notes too. It’s a really great episode.

And I loved the recommendation for Sex Education as well, which is again, such a great show. So lots of great recommendations in your podcast episode too. So yeah.

Pilar

Thank you. I’ll let her know.

Danielle

Yes. Great taste. All of them. I was like, yes, I love that show. I love that show. Because again, as you said, really great examples of representations that are not back in the era that we no longer need to be in. Things have moved on. Thankfully. Which is wonderful.

So when, and  this is not an easy question, but when you’re like looking at like… just the sheer volume of scripts that you read and the volume of students that you work with.. are there any particular patterns that you see emerging for students who are writing comedy or maybe they’re writing comedy dramas that you find yourself giving advice on again and again? And that  answer may be no, because it may be that it’s different for all students.

Pilar

Well, we just hit on one just in this last discussion. Like for example, if they’re writing a high school comedy, they will always use a John Hughes model, because we tend to write the thing that… in a way, we tend to copy the models that influenced us. And a lot of times writers don’t even realize they’re doing it. And while you can really learn from the movies that influenced you, and you should, you have to take all that plus your own experience plus what’s happening in the world, right? And put it in a blender and turn it into a great smoothie. And that part is something I sometimes have to push comedy writers to do.

You know, what comedy can come out of what’s happening right now, not like this buddy comedy formula that you grew up with. You know, you’re going to find yourself writing in a dated way if you’re just replicating what you grew up with. So I’m always kind of pushing people out of their comfort zone with writing comedy and making them really look around them and go, what’s happening right in the moment.

Danielle

Yeah, that’s such good advice. I think that’s really good advice for all genres too, but particularly as you say, with comedy. So I love all the things that you’ve covered so far. And what I’d love to ask about next is, in your book, you very simply but elegantly identify a model of trauma, training, trials and triumph, which I thought was just such a clear, practical way of not getting overloaded. Because again, you’re amazing at going into really forensic detail about things, but sometimes it’s also helpful to have those really broad structures too. How did you start to think about that model and do you feel like it applies as much to comedy as it does to drama?

Danielle

I think it absolutely does. I want to let you know something. So the Coffee Break Screenwriter that you’re referring to, the last edition I believe was 2016 or 2017. And there is an update I really want to make on many things. For one thing, I would change the pronouns. I was so proud of myself for all the he-she that I did and then my non-binary oldest child was like, yeah, there’s another way to go. So I wanna change the pronouns, I wanna change the examples. But the reason I’m bringing that up now is because I also want to change the model you just said, the structural model from trauma training trials and triumphs to trouble training trials and triumph. And the reason is when I said trauma, my feeling was, you know, Act one creates this sort of like we are sort of we’re shaken out of our comfort zone, you know. So it could be a positive or negative trauma, right? Something happens that’s negative or, you know, the trauma of falling in love. But a writer, just one writer wrote to me and said, you know, I’ve experienced real trauma in my life and I feel uncomfortable with this.

So I’ve changed it from trauma to trouble, which makes complete sense. And I’m not sure why I didn’t do that to begin with, okay? Except that maybe I was being a little dramatic. So I’d like people to think about it as trouble, training, trials, and triumphs, and actually might feel more comedy friendly that way. So yes, it absolutely applies to comedy, right? Because in act one, you know, a character either gets in trouble or has trouble thrust upon him or both. Okay. And that leads them to training, okay, where they’re kind of in this new experience and they’re trying to figure it out and they’re learning on the job, right? And they learn the rules of that and they learn who their friends are and who their enemies are.

And then in the trials part in Act 2B, right, now they’ve got to test all that out and they’re often on a mission and there’s a lot of pushback, you know, or the antagonist comes to get them. And so that’s why I called it the trials part. And the triumph part in Act Three is not movie, not Hollywood triumph, because if in a drama, sometimes people have to die to complete a mission. Okay. And in comedy, you know, often it is a series of awkward events that gets you to completion, but you do get to completion, you know? So it can be messy, but it’s still the triumph of completing a story of solving a problem of getting and completing a mission.

So that’s what those four things mean. And again, I apologize for the rambling answer, but I did have to say that because it’s bothering me that it’s there and I can’t fix it right now. I can’t go into everybody’s books and with my red pen and maybe I can sneak in in the night and, you know, like the tooth fairy.

Danielle

It’s great that you’ve updated it here. And that’s also just one thing that I massively respect about you as a teacher, that you spoke about really feeling like a teacher at the beginning. And you remind me of the very best teachers. Like the antithesis of that is someone who studies their subject for a period, say becomes an expert at college, and then that is what they continue to teach with sort of minor updates, whereas you, because you say you’re so actively involved with writers, and I get the impression from your podcast that you just learn from and respect everyone. Like it’s a wonderful podcast episode with Rita, your daughter, and I learned so much from listening too. Because you’re taking in all those inputs constantly.

It means that you are someone then who is able to change, in the way that you’ve said that we kind of need to as writers. We don’t want to be frozen in a period that was right for that period, but language changes, culture changes, our understanding changes. Like you say, there’s so many things thankfully now that we’ve had the opportunity to hear as feedback from people. And there’s so many things again, in my own experience like working and being on a board with different charities in the LGBTQIA plus space, where I’ve just done so many things where I think, oh my gosh, I wish I could time travel back and change how I wrote that or how I said that. But the opportunity now is that it’s like, oh…but now I get to, and that’s what’s the most important thing. So thanks so much for giving that update. And trouble for comedy. It’s fun. I like it.

Pilar

Right. It sounds more comedic for sure. And thank you for saying that about the podcast. You know, you’re a podcast host and I’ve been podcasting for 800-something episodes.

Danielle

Oh wow.

Pilar

Yeah. And I can’t remember at what point it was that I just realized like, oh, my only job on this show is just to sit back and learn. And once I had that philosophy of, yeah, I’m just going to be the student for an hour, the show got so much better instead of it always being about, yes, I know…I can’t say I’m not guilty of that still from time to time, but for the most part, if I just go, I’m going to sit back and learn, it makes me a better teacher. It makes for a better show.

You know, and everybody learns a little something and it’s just the easiest approach to podcasting, like my job it’s pretty easy on that show.

Danielle

I’ve not been doing this for 800 episodes, but there’s sometimes where it’s just like, is this even legal that I get to like hear all these things, write all these amazing notes, learn all these things and apply them. It’s just such a fun privilege. So awesome.

So I’m going to take a bit of a left turn now, back into craft and ask you a little bit about dialogue. So one thing I really loved from your books was this idea of verbal games. For example, you mentioned guess my secret, or tell me you love me. I wonder for those who haven’t yet read your books, if you could speak a bit more to what you mean by verbal games and how they can really bring comedic dialogue to life.

Pilar

Absolutely. And it is my favorite part of  teaching is talking about dialogue. Yeah, think about any dialogue-driven scene as a game in terms of the name of the game being the agenda of that conversation. So like you said, it could be tell me a secret, tell me you love me. That’s the name of the game. That’s the agenda. How do you play it? Well, that’s where your verbal strategy comes in of… maybe you play it by…sharing stories, maybe you play it by sharing jokes, maybe you play it by listing statistics till the other person corrects you enough. So there’s all these different verbal strategies, that’s how you play the game. So if you know what your agenda is, that’s the game. If you know what your verbal strategy is, that’s how to play it. And then you can ask yourself, well, who wins and how in this game of my dialogue?

And that will help you kind of plot out your whole dialogue-driven scene. Now even when somebody wins the game, sometimes they kind of lose the scene, you know? I always go back to, I haven’t actually mentioned this in class for a while, but when Harry met Sally, okay, there’s this moment where he’s trying to get her to believe that, you know, every guy that she’s friends with really wants to sleep with her. And they spar back and forth. That’s the game of it. The game is, I’m gonna get you to believe this thing. The strategy is she’s going to list certain people and he’s gonna come at her with all the ways they wanna sleep with her. Well, he wins that game. He wins it because he does convince her. But her line is, ‘well, that’s too bad because you were the only person I knew in New York’. So he loses the scene. He loses a friend. And it’s just a really great way to show that like, yes, you know, you get your point out there, it was really gamey, but it can land on something where it still pushes the story forward. He won the game, but he lost the scene.

Danielle

That’s wonderful. And that’s really, really helpful.

You’ve already mentioned sequences like the set pieces with the bridesmaids. Are there any other structural things that you love to teach when it comes to comedy? Or ways of helping people think about that bigger structure or pacing?

PIilar

Yeah, you know, I have changed my thoughts a little bit about that over the years too. So I used to make everybody take their acts, which is, you know, act one, act two A, act two B, and act three, right? And I used to make them break them up even more into sequences. So they had to think about the goal, activity, and complication of sequences in between acts. That really works for some people who love taking those bigger pieces and breaking them down and analyzing them and then writing. There’s a certain mindset of writer that loves that, but there’s a certain mindset of writer that gets overwhelmed by that. So sometimes, like when I’m working one-on-one in my one-on-one coaching with clients, I’m like, let’s just figure out your main act breaks. End of act one, you know, the midpoint between 2A and 2B, the end of Act Two, and what you’re going to do in Act Three. And then I make them write. I’m like, don’t break it down anymore. Because what happens sometimes is they write toward that first act break, and they’ll find things along the way instead of analyzing it. And so my, I guess my point is structurally, as long as you know where you’re going to…What’s going to be the event and the emotional reaction to that event that launches you into act two? Write your way there. What do you need to set up to show this person’s life so that when this event comes we understand it’s a disruption and that will launch them in? Great, write it, because you will find things out about your character, your world, their rules. You’ll see setups that you can pay off later on that if you’re overanalyzing it, sometimes you get stuck in that outline model. So structurally, I’m all for just go to your key points now.

Danielle

I love that. Wonderful. So just a couple of last questions before we wrap up. And again, I will say, I love that you make space for so many different kinds of writers too, and still manage to make it really practical. So thank you. That’s great for all those people listening. So I would love to just ask about any particular favourite comedy characters that you have. And I know that that can be really tricky to think of, when we’re like pulling up all the spectrum of them. But for example, you’ve mentioned Bridesmaids. I just wondered if you wouldn’t mind pulling out an example from those or from a different show, if you’d prefer…just for what it was that you found really worked about the character for you, just so we could have that live example.

Pilar

So I’m wondering if this isn’t me also projecting because I love her so much, but Julia Louise Dreyfus and like, yeah, so Elaine in Seinfeld turned into, oh God, what was her name? The lead in Veep.

Danielle

Yes. I love that show.

PIlar

If you look at it, Elaine in Seinfeld, when she grew up, right, I think became that character. I think they’re just, they’re, you know a spectrum of the same person. And what I’ve always loved about Elaine…Elaine in Seinfeld was a real person who had a job, okay, who had ridiculous male friends, who had sex with more than one person and didn’t feel guilty about it. Who had life goals that kind of changed from time to time. She was human. And it was again, very rare to see a human woman on screen. So I just loved her. I loved, loved, loved her. And so she, to me, still stays sort of my favourite character of that time.

And then…years later, she became Vice President of the United States in something called Veep. And she was terrible. Oh, I think it’s Selena. Right. Selena Myers. Okay. So she became Selena and that woman was awful. She didn’t start off that awful. That was definitely, you know, where we, we empathize with her because we’ve all been in a job that we are underappreciated. Right.

And what we saw in the first season was a Vice President who couldn’t even get a meeting with the president, right, who had to do all the crap jobs, you know, that the President didn’t want to do. We’ve all been there in a job where we felt undervalued and doing all the work for the boss, right? So that made us empathize with her. And then they gave her an arc that was reflective of our political system, so that by the end of the show, she had really crossed over from being somebody we empathize with to somebody who was a villain. And that may not have settled right with everybody, but it was very true. Again, it was shining a light on politically where we see some noble people in politics turn into monsters and show how power corrupts. So that doesn’t sound that funny. But watching how that happened to her, they showed the absurdity of it, which made it funny. And then lastly, her clothes. Oh my God, Elaine’s clothes in the 90s and Selena’s clothes in the 2020s. Oh my God, I just, I died. So I would dress like her all through the years. So yeah, those are my, so hats off to her. She’s my fave.

Danielle

She is incredible. And yeah, it’s lovely thinking about them in parallel like that, that arc. But yeah, that’s wonderful. Great example. So final question… I’d just love to know if there’s any advice you think given that you found helpful or find yourself applying.

Pilar

Any advice for what?

Danielle

For writing or having a career in the creative industry.

Pilar

Sure. Well, one thing that I’ve noticed that’s a constant with the people who are on my podcast is their chill. And it’s something, because everybody’s like, you know…What’s the secret sauce? You know, what’s the formula to success? And here I’ve had all these people from all parts of the industry, but they’ve all achieved a certain amount of success to be there on the podcast. And the thing that unites all of them is that they kind of go with the flow. They have their eyes open. They’re not always pushing their agenda. They’re kind of chill. They’re easy to get along with. And I realized…Oh, that’s the secret to success, you know, is try and be a pleasant, open person rather than pushing yourself on everybody all the time. And that doesn’t mean you shouldn’t have drive. But, you know, sort of maybe a work drive and just a personal chill. Put those two things together, you should do pretty well.

Danielle

That’s incredible advice, which I’ve never heard anyone give.

And it makes so much sense and it’s probably, well, certainly very reassuring to me. I think that’s great writing, career and life, and being a human advice. So it couldn’t be better than that.

PIlar

I hope so.

Danielle

So before we end, where should people go if they want to find out more about you and your work? And of course, I will put this in the show notes.

PIlar

Sure, sure. So onthepage.tv, like television, is my website. It’s a catch-all for everything. You can sign up for my Zoom classes there. There’s a link to the podcast there. There’s even a link to the publishing company where you can buy the books. But I would love to see everybody in class. It’s a lot of fun and you will get things done.

Danielle

Yes. I don’t doubt it. Thank you so much, Pilar, I really appreciate your time.

Pilar

Oh, you’re welcome. It was a pleasure.