Playwriting Teaching Drama

Teacher/Playwright Robert Wing

Written by Lindsay Price

Episode 74: Teacher/Playwright Robert Wing


Robert Wing is not a drama teacher (although he played one for a bit when the drama teacher broke his back) nor does he have any drama training, or even any writing training. He’s an English teacher who doesn’t even do all that much creative writing in his class. So why is he so good at capturing the teen voice through drama? Listen and find out.

Show Notes

Episode Transcript

Welcome to TFP, The Theatrefolk Podcast. I am Lindsay Price, resident playwright for Theatrefolk. Hello, I hope you’re well. Thanks for listening.

So, it’s really important to us here at Theatrefolk global headquarters that we put plays into the world that capture the teen voice, that the teen voice is out there, and not only that, we want plays that provide an expression of the teen voice – an artistic expression, a theatrical experience. That is key. That is key. That is necessary. That’s what we do, that’s what we are, and just find when you have this combination in a play – that teen voice, that expression, that theatrical experience – it can be quite magical.

And that’s one of the reasons I love writing for teens because it’s the one place – I’m sure I’ve shared this before; it’s my favorite thing, so, you know, bear with me – but it’s the one place that students, where a group of people can be affected by theatre these days. I fully believe. They hear their voice expressed. They realize they’re not alone. They can and they do. They make changes in their life because of something they see on stage. That is an amazing thing to play a very small part in. And I think this is the reason why the arts are so important in school because the arts are a method of expression that doesn’t happen on a daily basis in the classroom and, oh, there is no other group of people who has so much bottled up inside of them that needs to get out, that doesn’t necessarily have a proper channel to get out – if that makes sense.

I just think that’s so necessary, and this leads so nicely into my interview today. So, today, I’m going to talk to one of our playwrights, Robert Wing. He has two plays with us – Just Girls Talking and Scarlet Expectations of a Drowned Maiden and Two Greek Queens – and Robert is not a Drama teacher. He did play one for a little bit when the Drama teacher broke his back, but he doesn’t have any Drama training, and he doesn’t even have any writing training. He’s an English teacher who doesn’t even do all that much creative writing in his class which is stunning when you read his work and you realize he is so good at capturing the teen voice through a theatrical experience.

So, how is he able to do that? Well, all right, listen and find out.

Lindsay: So, I am here with Robert Wing. Hello, Robert!

Robert: Hello!

Lindsay: Hi! And so, Robert is a playwright and also a teacher. He has two plays with us. One is called Scarlet Expectations of a Drowned Maiden and Two Greek Queens.

Robert: It’s a mouthful.

Lindsay: It is a mouthful but it’s a very explanatory mouthful. I love that it gets all the nooks and crannies of what’s going on in that play. And then, also, Just Girls Talking. But, first of all, we sort of want to start off with you and who you are because your day job, you are not a Drama teacher.

Robert: No, I am not. I’m an English teacher who, in his second year of teaching, I was walking down the hallway and the principal approached me and said, “You’re the Drama teacher!” and I said, “Why?” and he said, “Because the Drama teacher broke her back in a motorcycling accident.” So, I became the Drama teacher for a year and I had no experience with anything, and I had zero budget. And I said, “I have to put on a play?” and he said, “Yes!” and I said, “Okay. Well, I can do this. What resources do we have?” and I found that we had a closet filled with prom dresses from the 1980s that had been donated to the program. So, I said, “We’ll do a play that takes place at a prom in the 1980s,” and there weren’t any so I wrote one and that was it!

Lindsay: Just imagine how resourceful we have to be when we have nothing.

Robert: I had all of those prom dresses, too! I mean, the girls were pretty shocked when we got them in them because they were hideous 80s dresses and so I created a play about it and it was one of the first I got published. I waited about seven or eight years before I actually submitted one to a company. Took a long time.

Lindsay: Why did you wait so long?

Robert: You know, it’s odd because, as an English teacher, as an English student, I don’t teach a lot of creative writing. I’m very much the teacher you want to go to when you want to learn how to write a really good persuasive essay, or even with reflective work, I don’t do much of it but I’m a really strong technical writing teacher. And so, when I wrote these plays which I think went over pretty well. The audience seemed to like them and people approached me with feedback saying, “You know, you should try to sell that. I’ve seen a lot of young adult plays and yours is good,” and, “Your play is good,” and I didn’t quite believe them because I didn’t have much experience with young adults plays. I hadn’t seen any!

And, what had happened was, what the principal finally did was he replaced me with a real Drama teacher, a woman named Erin Galligan, who teaches at a school not too far from me. Now, she’s brilliant and she replaced me and I was so grateful. And I had one of my scripts that I’d written because I was spitting these things out and she said, “I think there’s something quite good here. Can I direct it and it take it to a festival?” and I said, “Well, what’s a festival?” and she took it to a festival that won and I didn’t have any clue what was going on. But I went to the festival and I saw what the plays were like and what the vibe was like and I thought, “Oh, I get it! I see what’s going on here,” and I really liked it. I liked writing for the kids. And so, Erin said, “Do you have another play?” and so, I did have one but it was actually a classroom writing assignment I’d done where I’d taken Romeo and Juliet and broken it into six days for instructional purposes and, the next year, she asked if she could take that one. Well, that one won again.

And then, I thought, “I think I’ll submit one for publication,” and I started it. But that doesn’t mean anything because you get rejected too and it kind of stinks. Oh, and after the first rejection, I couldn’t send another one out for two years for embarrassment. It was just too…

Lindsay: Oh! Ugh! It happens all the time, you know? Like, it’s a common occurrence. It’s so funny. You’re like a… You’re a total sink-or-swim kind of… It’s been a total sink-or-swim kind of experience in terms of writing. You’re just sort of, well, I’m going to do it. I totally really relate to that in that, if it’s not around, well, you do it.

Robert: Yeah, that’s what you do. And I kind of discovered that, though, when I was in high school – I’m not being entirely truthful, I did have some involvement with my high school’s Drama company. The teacher who broke her back, the year before she broke her back, I went to see one of her shows and I said, “Oh, I’d really like to do sets and costumes for you,” because I love to do sets and costumes. Love it. I love all the backstage stuff, but I never had a desire to be on the stage myself, although I’m a teacher so you’re kind of on one.

So, I started doing her sets and costumes, and it’s still a real big love of mine. I love it. I’ve done The Crucible and really sort of avant-garde versions of Lord of the Flies and things like that. So, my first love is kind of building the sets and the costumes. That’s really fun.

And so, I discovered that I was kind of a theatre geek in a way that I didn’t know and I liked the community of the actors and it’s really fun. I also discovered that I’m not a director because directors have limitless patience and they speak this language that I do not speak.

I had to direct one play and the rehearsal was going so poorly, I took my shoe off and I threw it to the back of the house, out to the stage, and I said, “This play is rubbish!” and I had to apologize to the students. So, I don’t have that kind of patience. I think it’s a different art form.

Lindsay: Skill set.

Robert: It’s just entirely different.

So, I’ll create plays for directors and then it’s fun, and being a part of the audience, sitting through the rehearsals and, I mean, blocking, I don’t know how anyone has the patience for blocking – it’s the most tedious thing in the world – but directors do it and they…

Lindsay: Oh, I love… That’s one of my, I don’t get to direct very often anymore but that actually was always my favorite part because you’re creating, it’s about creating pictures. And can you create a picture that visualizes the text?

Robert: You know, when I watched, I worked with a woman named Sherri Spurdle also, and her background is directing and choreography, and every single hand extension, everything is so precise to telling the story. Once director works with it and you get their feedback because they will tell you what doesn’t work.

Lindsay: Well, it’s the whole community nature of what a theatrical production is, right? I try and tell playwrights all the time, it’s like, it’s not putting words on the page is really only the first step; it has to be put into a director’s hands and it has to be brought to life by actors and it’s not until that step happens where everybody is involved that it actually becomes a play.

Robert: And, as a writer, you have to listen.

When my students say, “You know, this line doesn’t work,” you really have to listen, especially if you’re writing for people who are significantly younger than yourself. I’ve had actors say, “You know, we wouldn’t say that, Mr. Wing.” So, I’ll go, “Okay.” You have to sort of swallow your pride and say, “Well, gee! Okay. All right.” And I like the process. I enjoy it very much. I kind of miss it because I’ve taken a bit of a year off this year and I’ll see the kids in the hallway and they’ll say, “Oh, what are you working on? What are you working on?” then they’ll, you know, “Keep me informed,” but I’m missing it.

Lindsay: That means you’ve got to write another one. If you’re missing it then that means it’s in you.

Why do you think that you write so well for youth? Like, one thing you said was that you listen to them, that you get their language right, but where do you think? Do you think it’s because you’re in the classroom and you hear them all the time? What do you think it is?

Robert: I think it’s more than just being in the classroom. I have a very, very strange distinction of actually teaching in the high school that I went to for my sophomore, junior, and senior years, and I didn’t enjoy high school. I never, ever, ever thought I would be an English high school teacher. I trained, I took a degree in English, and it was my last year of college, and my advisor said, “You know, you only need to do an internship,” and I said, “I’ll do it, why not?” and I student taught at junior high school and swore I would never go into the classroom again because I was about twenty-three, it was just awful.

And so, I became a social worker and then I learned a whole new definition of awful. And I did that for about seven years and I quit that job – it was the only job I ever quit – and I travelled and I was at my sink one night and I was washing dishes and the telephone rang. There was a woman on the phone and she said – I was thinking at the sink, “I have one more month before my money runs out. What am I going to do?” She said, “Is this Robert Wing?” and said, “Yes.” She said, “Are you a teacher?” and I said, “I don’t know because I’d never paid the $200 for my license,” and she said, “You have a background in mental health, don’t you?” and I said, “Yes.” She said, “Well, we’ve had two teachers quit in a month. Can you come in?” and I said, “Oh, God. I don’t want to but, okay, I’ll try it,” because, you know, I need the money. Well, I walked in the classroom at thirty and I absolutely loved it.

So, whatever happened in those seven years or eight years needed to happen. I walked in and I absolutely loved it, and I absolutely had a sense of, “This is where I’m supposed to be,” and I like these kids. I like how they talk, I like the way they interact with each other, and it’s strange because I’m reliving high school over and over and over from a slightly different vantage point. And I really like it! And I didn’t think I would.

So, at age thirty, I discovered my calling without having, you know, sweared I’d never go back to the classroom. But I think the seven years as a social worker really helped me gain some perspective because I know what their families are like where they come from. I live in a very, very poor area – rough area – and I love it. It’s very, very beautiful. It’s very beautiful. It’s Vermont. It’s the Northeast Kingdom of Vermont. It’s very beautiful. But I understand where these kids are coming from and I listen to them and, somehow, it just translates. It just works and I never patronize them, ever – ever, ever, ever. It’s a rotten thing to do. I respect them and, if you have no interest in the future or youth culture at all, you should not be an educator. You really shouldn’t be because you’re surrounded by youth and you’re swimming in it – in their angst which is a word that I used to despise because I once went to a festival after a few years afterwards and I wrote a play and they gave me a special award for Best Teen Angst and that really strung. I told my mother the next day, I said, “Oh, mother. I’m so angry. I got Best Teen Angst – what rubbish is that?” My mom said, “Rob, you write the best teen angst.” And I said, “Yeah?”

Lindsay: You won!

Robert: She goes, “John Hughes wrote great teen angst.” I went, “You’re right!” I mean, come on! So, it’s sort of my genre. And I think it’s…

Lindsay: You know what though? I’ll tell you. It doesn’t come across like teen angst at all.

Robert: Oh, good!

Lindsay: Like, it comes across as – particularly in Just Girls Talking – it’s very honest talk and I think that…

Robert: Well, so is John Hughes.

Lindsay: Well, yeah, and I think that that whole nature of listening and not patronizing. I mean, that’s the question I get all the time. You know, “How can you write for teenagers?” and I always think, “Well, it just hasn’t changed that much from when I was a teenager, like, emotionally,” you know? And that’s what that teenage – it’s a poor word to say “teen angst” but there is a very specific emotional thing that happens when you’re a teenager, you know? And some people call it teen angst but it’s there and it’s always been there. We’ve all been through it. Some people just forget.

Robert: And, also, I think they trivialize it and I think, “Oh, no! Those traumas you experienced when you were sixteen change you forever.” And, also, people talk about high school and they say that, you know, “It’s not like real life,” and sometimes, I say, “Well, you know, it’s quite like real life.”

Lindsay: Oh, my God. Have you been in an office building? All it is is it’s high school with money, you know?

Robert: A teachers’ lounge, are you kidding?

Lindsay: Yes! Yeah, that’s all we’re doing is reliving high school over and over again.

Robert: But I also, I don’t know, it’s like Skype – what we’re doing right now. I have no real interest in technology, I don’t. But I find that, because of the kids, I feel the need. I need to understand the language. I need to understand how they interact with the world so I make myself do these things. You know, I rarely use my cellphone, I rarely text. I just don’t do it! What makes these kids tick and how do they communicate? So, I like my job very much and what I’ve done with my plays is just an extension of what I do in the classroom.

And, well, I’ll tell you what writing has done for me. It has made me a far more compassionate teacher.

Lindsay: How come?

Robert: Because when I put my stuff out there and someone says, “No, not good enough, sir,” I thought of me saying to countless children, “Not good enough, sir!” But, I mean, of course, I couched it kindly but it hurts! It hurts to be told that you’re not good enough or, you know, talk about feeling like you’re sixteen again. Get your first rejection letter, you’re sixteen again/

Lindsay: It’s to the point where I really, when I send out rejection letters, it’s a very, very conscious effort to not do either of those things because I know what it’s like to get both.

Robert: Because you put it out there and it is, you know, kids will often ask me, they’ll say, “Well, which character is you?” and I say, “Darling, they’re all me!” It’s just vain gloriousness. It’s this God complex in a sense of, you know, every one of these characters was filtered through me and, when someone says, “Not good enough,” it stings. And the teen angst – not to get back to that but – that really, I think people miss the point entirely because I think something like Just Girls Talking is about everyone experiences that, every stage in their life, you know? And questions about…

I’ll tell you something else, when you write about young kids, and whenever my plays deal with this – or young adults, I should say – is the question of justice. It’s very well for young audiences to understand fairness.

Lindsay: Yes, yes, yes.

Robert: To understand and fairness. And, if you serve them up some platitudes like, “Oh, in the end, cheaters never win,” well, that’s not always the case and you have still give them hope that it’ll be all right and you just keep treading along and hope for the best and try to, I don’t know, send some kindness out into the universe.

Lindsay: So, talk about this – now I’m dying to know – because everything that you seem to have in terms of writing comes from an instinct, because I’m assuming you haven’t taken any writing classes.

Robert: I’ve never taken a writing class in my life.

Lindsay: Okay. So, it’s all instinct. So, what’s it like for you to write a play? What do you do?

Robert: Usually, I have a colleague who writes copious amounts – he writes a lot, a lot, a lot, a lot – and I said, “Well, do you revisit? Do you revisit?” and he says, “Not so much.” His process isn’t about that. He’s very, very quick. I might spit out ten pages of a draft and then put it away for three months, and I pull it out and I say, “I think there’s something there,” and, truth be told, I have a 27-mile commute to work and back every day through the beautiful countryside, and that’s usually where I do all my thinking. And, you know, I have the conversations, the dialogue between my head for weeks and weeks and weeks about what the characters say to each other and then I’ll put it down on paper and then I’ll put it together again in my head. I think it’s… I love my job and I’m very, very fortunate that it’s how I make my living.

So, I think of writing as this wonderful thing that I get to do on the side, or writing is often a gift. There’ll be a student that I’ll really, really, really just admire. You know, they’ll work it so well on that stage and I’ll go, “You know what, I’m going to write a play for her,” and that’s actually two plays last year, I had one kid in mind. She was a graduating senior and I went, “I’m going to do that for her.” So, I’ll spend weeks and weeks, and sometimes years, thinking about where the play will go and I know that sounds insane because twenty-five pages to take a year on, that’s nuts! But I enjoy it. It’s a very indulgent process for me and I now produce a script and then I give it to a director and then the conversation starts.

Lindsay: Now, both the plays that you sent to us were second submissions.

Robert: Oh, you’ve got to believe it.

Lindsay: So, what happened in the time between the first and second submission?

Robert: I saw the rehearsal and it was a nightmare!

Lindsay: Oh, why? Tell me why.

Robert: Because I got talking. I thought, “You know, I’ve done this, I’ve done this, I’m going to send these out without seeing it staged, without running it through my director.” I sat in on the first day of rehearsal in that darkened auditorium with the actors with their scripts and I just thought, “Oh, dear Lord in heaven, what have we got going on here? What a wreck!” and I was just so ashamed. And so, I sat in the audience for weeks and just slashed and burned and slashed and burned.

And, also, characters had to evolve. All the clichés are true. You know, it is nothing until it’s acted on a stage. Until it’s filtered through your actors and filtered through the director, it’s nothing because it might be the most vivid thing in your imagination but – oh, good Lord, it was awful. Two stinkers, two real stinkers! And it’s all vanity! I just thought, “I’ve done this, I’ve done this,” and no, I hadn’t done it. I hadn’t done the work and it showed. And then, I felt very, very embarrassed, very embarrassed, and then I felt a little ashamed because I thought how I’m wasting the actor and the director’s time. So, you kind of eat humble pie and listen and I did it.

And then, it started to become a play again which is a lovely process. I love the last because, at my school, Sherry and I usually do a very, very long rehearsal period. We’ll do three months for a one-act play.

Lindsay: How wonderful is that?

Robert: Are you kidding? You have a troop of actors who are yours. I’ve three months between that first script. The first script the actors see is typically about a fourth or fifth draft for me – typically. And, so then, there might be eight drafts by the time it’s done. And so, it’s been filtered again and again and again, and scenes have been run and run and run and moved around. I cannot stress how important work with a director is. It is so important. It is important and I love the process, except the blocking!

Lindsay: Yeah, but that’s the director, that’s their job. You can just sort of sit back and see the outcome.

Robert: Yeah, although it’s great because I know when it’s good because the last two or three weeks before the show goes up, it’s new again. And I’ll look at Sherry and she’ll look at me and we’ll just kind of nod and go, “Oh, we’ve got a show here. We’ve got a show,” and that’s a great feeling and I love it because I like dialogue very, very fast and lines are just supposed to ping, ping, ping, ping, ping. And, when actors find that rhythm, it’s so satisfying. I love it when they hit their stride and the lines are just flying. And, because I don’t have a lot of experience prior to becoming a teacher and working with the theatre, I know that there’s a time for everything and things evolve, but I was an outsider coming in and thinking, “How does this happen? When does that magic happen?” and there was this couple of weeks. I love that part when it’s finally a play and it’s beautiful. Well, the process is beautiful.

Lindsay: Yeah, it is beautiful. It’s sort of a, well, it takes on a life. And then, you bring the audience in.

Robert: I hope it takes a life! And that’s another experience because, when you perform for an audience, I’m watching the audience. I’m really trying to see which lines elicit which response because I’ve written lines, thought they were quite serious, that elicit giggling and I thought, “Oh dear. I have to go back and cut those.” And there are certain jokes and certain pauses that you create and you make sure they’re in the script and you hope they work and you hope they work and I watch them. There’s actually a window in the auditorium, kind of in angle to the stage, and I can hide behind it and watch people because I’ll sit with the script and go, “Oh, that’s not so good.”

I once went to a presentation, David Sedaris, the humorist, the writer, I don’t know, it was brilliant, and he came to Burlington.

Lindsay: I just saw him there two weeks ago.

Robert: But did you notice, when he was reading, he had a little pencil, he’d make little marks?

Lindsay: Yes, he makes notes! He makes notes as he goes. That was my favorite part.

Robert: The questioner said, “What are you doing?” He said, “I’m marking it when people laugh.” It’s that simple! If you’re writing a comedy, you have to know when people are going to laugh. So, that’s what I do.

Lindsay: And when I saw him, it was the very beginning. So, it was like stories that he had just told a couple of times. So, it was like, as a writer, and we were write up close so it was a totally satisfying thing to watch that happen.

Robert: I love to watch other people’s process because, when you create, it’s such a solitary thing. You watch someone else do it and you realize they have the same insecurities that I have of, “Gee, that line won’t work,” or, “That transition doesn’t work,” or, “I’m losing people here,” and it’s very satisfying.

I’ve discovered that quite late in laugh that the process, the act of even talking about writing, because it’s something I never did, I’m a very technical writer and so the whole creative side of it, the fiction, it wasn’t my thing, and I didn’t know I had a voice for it but I guess I kind of do and it’s really fun.

Lindsay: Awesome. Okay. So, as we wrap up here, as an outsider, what does theatre mean to you sort of as you dipped into this world? Coming out as an outsider, what does theatre mean to you?

Robert: It’s incredibly warm. It’s hard to describe. It’s like an island of misfit toys all get together after school and they try to make something meaningful and they try to make something beautiful and it’s charming and it’s very much what every teacher wants to do in his or her own classroom but rarely happens. But there are these like-minded people who sort of gravitate towards an auditorium who do it and I love it. And I love writing things for kids. I love, love, love… For example, I just saw a version, Sherry did a version of Little Shop of Horrors and her main actress, a lovely young lady named Shannon, I’m thinking, “Oh, she’s a senior next year. I’ve got to write a piece for her, I’ve just got to,” because she’s just so full of life and fun and kindness. I just want to give her something.

Lindsay: What a lovely gift that you can give your students. Like, “Here’s a play just for you.” That’s awesome!

Robert: And I keep their names. I actually usually characters, I say, “This is inspired by you,” and sometimes kids will say, “I said that one! You wrote that down, I said that!” and I went, “Well, maybe I did!” So, you know, I’m always lifting things the kids say.

Lindsay: Ah! Very nice. Lovely. Robert, this has been an awesome time. Thank you for sitting down and having a chat with me today.

Robert: It’s very kind of you.

Lindsay: Awesome! And so, yes, everybody we need to check out – I’m going to read the title correctly – Scarlet Expectations of a Drowned Maiden and Two Greek Queens and Just Girls Talking.

Okay, Robert. Have a good night!

Robert: Thank you. Buh-bye!

Thank you so much, Robert. I really enjoyed, I really enjoyed this conversation.

Okay. So, before we go, let’s do some THEATREFOLK NEWS.

All right, I’m talking to you. We’ve mentioned this a couple of times on our Facebook and we did another podcast on this but are you working on your World Theatre Video project? I know, I know, you’ve only been back in school a couple of days, but the deadline’s coming up, it’s January 25th. It’s very simple. You know, you take a monologue which the monologue’s already chosen for you. It’s on the website,, and it just happens in the December-January slot to be one of my monologues so I’m so happy. I can’t wait to see what classes and groups do with it.

So, all you have to do is you take the text, find a way to visualize it – perhaps with tableau, maybe with group speaking, individual speaking, maybe you use pictures, you know? Come up with something, film it, you don’t even need to get fancy. Pull out that phone if you have to. Send it in. Go to for more information. If you practice project-based learning in the classroom, if you need to find a way to incorporate more technology in the classroom, what an excellent place to start, what an excellent project. I’m so happy and thrilled to play a part in it.

And, finally, where, oh, where can you find this podcast? We post new episodes every Wednesday at and on our Facebook page and Twitter. You can find us on You can find us on the Stitcher app and you can subscribe to TFP on iTunes. Go over there. Search on the word Theatrefolk.
And that’s where we’re going to end. Take care, my friends. Take care.


Music credit: “Ave” by Alex (feat. Morusque) is licensed under a Creative Commons license.

About the author

Lindsay Price