Zibby chats with Golden Globe and Emmy Award-winning screenwriter and director Cindy Chupack about WE WAITED FOR YOU, a beautiful picture book that celebrates the moment a child and parent form a family. The two discuss Cindy’s literary journey and the impact her 2004 essay collection, THE BETWEEN BOYFRIENDS BOOK, had on readers, including Zibby herself. Cindy also reflects on her divorce, the challenges of infertility, and the emotional journey of adopting her daughter. She even describes a recent painful breakup, which she humorously considers as material for future writing. The conversation touches on themes of love, resilience, and the therapeutic power of storytelling.

Transcript:

Zibby Owens: Welcome, Cindy. Thank you so much for coming on “Moms Don’t Have Time to Read Books” to discuss all of your books. You were just at Zibby’s Bookshop for your new children’s book. I’ve been a lifelong fan of Between Boyfriends, now The Longest Date: Life as a Wife. I’m just a fan across the board. Thanks for coming on.

Cindy Chupack: Thank you for having me. You’ve had so many of my favorite authors. I feel excited to be in the company of all of them.

Zibby: Your Between Boyfriends Book has literally moved with me from whenever it came out. When was that? Do you remember what year that was?

Cindy: 2008 or something. It might have been earlier.

Zibby: 2008, yes. So many times. I’ve been through divorce and remarriage. This book just keeps coming with me no matter where. It’s like a little talisman. Thank you.

Cindy: I’ve been listening — I need a way to display a bookshelf of audiobooks. I’m always driving, and I listen to a ton. I especially love ones read by the author. I’ve been listening to Samantha Irby’s latest one. I love it. I’m so obsessed with her. She’s working on And Just Like That with some friends of mine, so I said, “Tell her I’m obsessed with her.” Then I guess she said that she had my Between Boyfriends Book, which made me so happy because authors that I read when I was just starting out, like Cynthia Heimel and Merrill Markoe, Nora Ephron, that wrote essays about relationships that inspired me. It’s just exciting to me, the continuum. I feel like Samantha’s work now is inspiring me back. It’s nice to be part of that.

Zibby: Great. That’s so great. Start out by talking a little bit about your children’s book because I know your children’s book is your most recent. Loved the whole story. That, of course, is sort of the update on where you are with your own life, as we followed you through all of your essay writing and career and everything. Maybe start there, and we can work backwards a little bit.

Cindy: We Waited for You: Life as a Wife — sorry. The Longest Date: Life as a Wife.

Zibby: The Longest Date: Life as a Wife.

Cindy: We Waited for You: Life as a Wife could be a book because I’m also divorced. Waiting. We Waited for You was a children’s book I wrote. Actually, children’s book production takes so long. I had no idea. I think mine took longer than usual. I wrote it because I adopted Olivia. The Longest Date: Life as a Wife is very much about being married later in life and wanting to have a child but just having to go through all the things that they told us we would have to go through, but you’re like, la, la, la, so all the fertility stuff and then trying an egg donor and then finally, adoption. It was such a long and hard process. I wrote that book, The Longest Date: Life as a Wife, because I felt like there was nothing out there that was honest but funny about that whole process. I really could’ve used that. You have friends who are pregnant, who are having babies. Some of my friends who were having trouble really had trouble with that. I felt like, I’m going to just be happy for everyone. It’s not a zero-sum game, but it’s hard when you’re waiting. It took five or six years to have her. Then I realized that there’s a little bit of a guilt that you tried other things first. Once you do have your child, you don’t really talk about that because you don’t want to say, we tried for years to have a biological child. I, of course, love my daughter Olivia. I wouldn’t want any other child.

I did feel there was sort of a weird empty space for parents who’d been through that. When you finally have your child, you want to be able to express, oh, my gosh, we waited for you for so long. We went throughout so much to get you. We moved mountains. It’s about that. It’s celebrating a child who comes into a family, no matter how, for all different kinds of families, whether the child’s adopted or gay parents or single parents, just the process of what it meant to get this child. I wanted to write that. Part of why I wanted to write it was — I was at her preschool. There was a tradition where on a child’s birthday, you took a book from the library, and you read it to them in front of the class. We picked one, The Day You Were Born or something. It was all like, you were in my tummy. It didn’t have anything to do with her. I felt like, I’m reading in front of these kids, I don’t know exactly how to go — I was thinking there should be a book like that. There are some about adoption. Jamie Lee Curtis has great ones about adoptions. There’s nothing that covers the spectrum of however a child came to you, whether in your tummy or — it’s all the same once you have the child. Just a little rhyming ode to that journey and to help children realize they were worth waiting for.

Zibby: It’s so beautiful. I know, it took me — I won’t go into my own journey here — a very long time to have my third kid. I had twins. Then we had this big, big gap. I always try to tell her, “This is just the way it was supposed to be. Right when we gave up, there you came. We were waiting for you. You weren’t ready to come.” Try to change who was in charge. It’s just these kids waiting to find us. It has nothing to do with us. We’re just hanging out over here.

Cindy: It’s true, the right kid, the right time. There’s a few illustrations in here that are families waiting for another child. I knew parents going through that same thing. It’s just as hard when you really want another child and have to wait.

Zibby: Your book is beautiful. The illustrations are beautiful, the whole message, oh, my gosh. When you say it took forever to come out or the process was slow, when did you first write it? How long until now? What happened in between that slowed —

Cindy: — She turned into a tween. She’s still really adorable and loving and excited about this book. She came with me to your bookstore for the reading.

Zibby: I remember.

Cindy: She likes being part of the story of this book. I think she was young enough to still be reading picture books when I wrote it. Somebody at Sourcebooks liked it pretty early on, but then it just took a long time to get an illustrator. They have eighteen months. If they’re booked up — then somebody fell through. Since I do film and TV, I just felt like — lots of things can happen in a couple years in television. You can get a lot of people and make a whole thing. Even though I love this story, it came pretty fast. It’s not a whole lot of text. It’s kind of a poem. I felt like, okay, I wrote it. Someone can just draw something. Let’s get this out there. It’s a long process. I’ve now learned how they work with illustrators and authors. You’re on a separate track. I didn’t talk to the illustrator during, only after. They do that to really respect the illustrator’s process as well as the author’s. They’re working with you, giving you notes. They have a vision for it. Unless you come in with an illustrator, I think that’s kind of typical and respectful to let the illustrator do their thing to add to your book. One plus one equals three. I finally got to know her afterward, Emily Hamilton. I really love her. It was fun to hear how she responded to the text when she first got it and how I .

Zibby: So sweet. I actually wrote a children’s book, but I’ve never even met my illustrator. I’ve met her on Zoom. She seems lovely.

Cindy: Same with me. She’s in England. I know, it’s a strange process that you’re not collaborating. The people who don’t collaborate for a living, I feel like maybe that would be harder. Maybe some authors would be very precious or .

Zibby: That’s true. Actually, maybe there’s a reason why they don’t let everybody so closely.

Cindy: There is. I did Zoom. I have it on my website, cindychupack.net. There was a Zoom I did with the illustrator and also a children’s book agent who really explained that, that it’s a very respectful process. That’s why, so that you don’t influence what they’re doing.

Zibby: Amazing. Sorry, I didn’t watch that. I can go back and watch.

Cindy: No, that’s okay.

Zibby: Let’s talk about The Longest Date: Life as a Wife. You’re so funny about everything, even though you can tell maybe it was sad at the time. Maybe it wasn’t. I don’t know. The way you write about everything is just hilarious. Your first marriage, your husband ended up being gay and then having another family. You had this hilarious essay about getting a get. I am Jewish and went through a divorce. I get it. I get the get chapter. You write about all of that and all your life phases and falling in love with the guy who you weren’t supposed to fall in love with and showing us time and again why. Then being able to highlight even great things about him, even though you’re constantly running into someone he had a threesome with or things like that, it’s so funny.

Cindy: It was always like, “Is there going to be someone at this wedding you slept with?” One time, he said, “Well, the bride doesn’t count.”

Zibby: So funny, oh, my gosh. I love that even in this relationship, you start off on such equal footing. Maybe not even equal, but when you have him over and you’re like, I have a really nice house. He’s like, I have a nice place too. Then something like, he said, I’m worried about leaving you. You were like, I could be the one who’s leaving you. I love the confidence and where you meet in life. Tell me a little more about writing this book and how you feel about it now given everything.

Cindy: I know, it’s interesting because we’re divorced now. I feel like all the stories were a little better. They ended, but still, we love each other. Now we’re divorced. I was thinking that in every relationship that goes wrong, you should end up with a child from it. Of course, I’m happy that we were married because I got Olivia from it, and all the experiences, but you can’t say that about every relationship you had. I got some good musical taste. Anyway, how I feel about it, I still stand by — when I wrote it, there was something in the intro where he said, this is going to be kind of ironic if we don’t stay together, if you talk about how great our relationship is. I said, it’s not going to be about how great our relationship is. I really wanted to show the hard things about being together. That whole “opposites attract,” I’m not sure that is a formula for success as you get older. I really wanted to write about marriage the way that we wrote about dating on Sex and the City and be just as open. I have the same attitude about writing about infertility. I feel like people kind of close ranks when they get married. No matter how much you used to joke about your boyfriends and your hardships, you’re married now, you can’t. I guess I like writing about things you’re not supposed to talk about. I wanted to write about the hardships you have sometimes, like if the woman makes more money or if he has habits you don’t like or the exes and also, what we went through, the fertility stuff, which actually did bring us closer together. I know it breaks up couples, but that’s not what broke us up.

He wanted to adopt from Africa. I wanted to adopt from China at one point. We just were in different breakout groups at the sessions. Then we finally decided to adopt domestically. It was a lot of negotiation. You’re talking about a child. Then other people have opinions too. There’s been a giant humanitarian problem in Haiti. You should adopt from there. All of a sudden, everyone’s got ideas. It’s like you’re buying a car or something. I wanted to just be able to write about all of that. My first book, The Between Boyfriends Book, it came after I had a column in Glamour called Dating Dictionary where I had punny little terms for each stage. The editor I worked with was great about helping me figure out to start from breakup to your next boyfriend. I had a lot of those essays beforehand. Then once we came up with that structure, it became clear, okay, I need more essays in here for during the breakup or while you’re dating or when you’re recovering. That was a really fun book. That’s kind of how I’ve written my books of essays, is just in little bite-size pieces. I really like that a chapter can be about something, but they don’t all have to become a giant opus on your life. That one, it still seems very beloved by people, like you said. I’m really proud of it. I felt like The Longest Date went a little deeper and did try to make more of a linear narrative about the process of waiting to have a child and getting married later in life and what that presents.

Zibby: Yes, it was great. It’s nice when, as a reader, you can go through all these things. I was trying to think of 2008. I was married, but recently married. Then we can go through it together, essentially, even though we don’t know each other. Now we know each other. I have all these authors who, I’m like, okay, they just through that, and now I’m going to go through that. It’s like a guidepost through life, so to speak.

Cindy: Sometimes you write about something — I actually wrote a movie that is sort of slowly coming true. I know when I was working on Sex and the City and we wrote about Charlotte’s infertility problems, I hadn’t gone through it yet. Then looking back at it, it was like, yeah, that was pretty on target. None of us had gone through with that yet when we were writing about it, but we knew people who were going through it. There’s things you write about that happen. It’s interesting. It does feel you’re going through it with people. I like that these books can be for a period of life so that it’s not only right now, as somebody gets married or is thinking of getting married or as someone is having a child. When you break up again, you can go back. I will say, even my children’s book, I felt like — when I wrote it, we were married. It was an amicable — we just kind of grew apart. There was no drama. It’s been great. I feel like I should write something about — it wasn’t as traumatic for Olivia. I was prepared for the, she’s going to cry and beg us to stay together. She was, I want to say, eight when we broke up. She had friends whose parents had divorced. It was more logistical for her. “At Dad’s place, can I have a bunk bed?” It was interesting. I think our baggage about what is going to be hard for a child to understand isn’t necessarily what they — they’re not going to have those issues. I’m proud that we could show her that we could still be happy and that we still want love and that we can be friends and be amicable. You should really still be madly in love with your partner or find someone else who makes you happy. I’m glad to be modeling that. It’s not going great, but…

Zibby: I want to hear what’s going on with you today.

Cindy: I’ve just written this long essay about it that’s made me think I need to write a new book. I’ve been listening to Samantha Irby and Nora Ephron, I Feel Bad About My Neck. I was in a relationship after my divorce. I was one of those pep talks. Cindy met a guy on a plane between New York and LA and had this amazing bicoastal relationship. He bought this farmhouse. We were drinking out of big goblets. It was like we were in this Nancy Meyers movie or something. This was for the whole pandemic. I was so deliriously happy. Then I just found out the day after the writers’ strike that he had been having an affair for two and a half of those three years with his housekeeper.

Zibby: Stop.

Cindy: She contacted me on Facebook. She sent me these texts between them where she said, “I thought it was just me and Cindy.” He said, “It is just you and Cindy.” I was like, what’s happening? I’m laughing now, but it’s been very traumatic. I was like, I don’t know if I can keep doing this. I will, somehow. It was rough. I feel like I went from the inspiring tale to a cautionary tale. I also feel like, why am I still going through this at this age? I’ve written about dating forever. I should know what I’m doing. I’ve been knocked for a loop.

Zibby: Oh, my gosh, I am so sorry. On the other hand, you keep getting all this material.

Cindy: I was a little bit out of material, I will say. I was like, you know, when you’re happy, there’s not as much to write about. Now I’m like, okay, thank you, universe.

Zibby: Oh, my gosh, I cannot believe that happened. I cannot believe it.

Cindy: I cannot either. It’s really been rough. People say, I hope it doesn’t make you question. You’re probably going back through it and thinking, how did I not know? No, he was really very compartmentalized about this, so there weren’t any signs. I don’t feel like I don’t trust men now because it was really hard to pull off. I feel like not many men could do this. I don’t know how I feel. Anyway, I’m back to my Between Boyfriends Book.

Zibby: Wow. The interior monologue that you have and that you share with others — this sounds hokey to say. It’s a gift, but seriously. As you’ve seen with the popularity of Sex and the City and all of the things you’ve written, there is something about how you write that just completely strikes a chord. It’s this mix of self-deprecation and the relatable things and saying the things, as you said, that people don’t want to say out loud, even if it’s not wanting to take care of a sick boyfriend or just things that you worry, oh, people will judge me for this. You just go out and say them. It is so refreshing and awesome. Maybe this is why you were here or something, to have all these crazy things happen to you.

Cindy: The piece that I’m writing, it’s kind of a travel piece. I had a past lives reader once tell me that I hadn’t had a good relationship since ancient Greece.

Zibby: Oh, my gosh.

Cindy: I was like, okay. Then when I got married, I was like, I did it. She said, “Your job in this lifetime is to learn to love and be loved.” I felt like I did it when I got married. I felt like I did it with this last boyfriend. When we broke up, I was looking for somewhere to go. I found this Healing Hotels of the World website. The one that really spoke to me, I was making a reservation — it’s in Greece. It was in the shadow of this ancient town of Greece. In the movie, I guess I should’ve met someone there, but really, it was just healing and good to be there. I was like, okay, I knew what I was doing when I was here once before. I feel like I’m not sure how many lessons — it’s therapeutic for me too, to write about when things don’t go your way. I think it’s therapeutic for me to write. It’s therapeutic to hear people relate. That’s why I’m doing it. I think that makes you feel like part of a community. You’re not so alone with these feelings.

Zibby: It’s so true. Wow. I want to read the essay. Did you sell it somewhere yet? Is it coming out?

Cindy: It’s funny. I sold it to elle.com so I would have more space because it’s online. As I’ve been listening to Samantha Irby’s, I’m like, she writes the longest, greatest essays. You could listen forever. I’ve done a lot of cross-training with writing because I like to write TV and film but also books and sometimes magazine columns or tell a story for The Moth. They all have different lengths. When you write an essay that could be in a book, it can be as long as you want. I wrote this piece. I worked with an editor who’s kind of Ryan D’Agostino, who I love. He helped me place it. We sold it to elle.com. He said, “Write it as long as you want.” My first version was nine thousand words. It’s supposed to be two. Then we cut it down to five. I’m hoping the editor will just let it run at that length because I feel like it should be at least that. I’ll send you the nine-thousand-word one.

Zibby: Oh, my god, I would love it. Seriously, I would absolutely love it. This is completely not true; I feel like now I’m entitled to the updates. I’m holding the book, waving it around. Okay, well, you shared all that, which of course, was .

Cindy: With We Waited for You, when I was going to go — my tour was basically your bookshop. I really did not do a whole lot of publicity, but I’m still so happy it’s out. Anyway, I was talking to the publicist. I said, “Is it going to be weird because I’m not married anymore? It was we. Should it be I now? Now I feel a little weird.” She said, “People are not expecting this to be autobiographical like your memoirs. They’re not interviewing you and going, why aren’t you a we still?” I still think of it like the whole extended family. I have to sometimes separate the work from — it’s hard to. It still stands. These things still stand.

Zibby: Do you still believe in love?

Cindy: That’s a good question. For everybody else. For everybody else, I’m always that cheerleader. It’s not over yet. I think I believe in it for me, but I guess in the movie version, this is the time where I’m supposed to be alone for a while. I’ve had a lot of boyfriends. Maybe I haven’t been alone enough. I’m really being a great mom right now with the strike and being without a boyfriend. I’m in it. I am in school. I feel like a dad feels when they drive their kid to school. Look at me. I’m going to school, and I’m a dad. Now I’m like, look, I’m here. I met the PTA. I’m volunteering. I’m trying to just be a good mom. I’ve been writing a little more travel pieces. I wrote one about going to Ojai with a tween, traveling with a tween. This movie I wrote that was kind of supposed to be the — anyway, this movie I wrote, it ended with — I’d always wanted to see the northern lights. My last boyfriend, we had this bucket list. We were going to do these things together. I’m really determined right now, I’m going to go see the northern lights with Olivia, with my daughter. I’m not waiting for the perfect boyfriend to go on this romantic, expensive trip. I just want to do it. She says it’s on her bucket list. Even though she’s twelve, she has a bucket list.

I’m in a place of, that’s love too. I had a surgery, and I had a friend come in. I said, “It feels weird not to have a partner in my life right now for these kind of things, in case of emergency.” I know we did that on Sex and the City. Suddenly, I’m like, who the hell is my “in case of emergency” person anymore? My friend said, “You have a million people who love you. You have so many friends. Just none of them are a man right now.” It really was good to remember that you’re not suddenly alone because your relationship ended. You still have all these people in your life. I still have Olivia. There’s still a lot of love in my life, so I’m going to just try to keep living my best life. I’m not going to try as hard right now. People go, you can get online and date. I’m like, I have done that so many times already. I’ve already sowed my oats. When I was divorcing, people were divorcing and getting married. That had been their whole life. They were like, I can finally date. I was like, oh, my god, I did so much dating. I’m dating again. I will be dating again. It’s not a novelty. I’m still hopeful. There’s something in me that’s still hopeful. Even now, I’m like, maybe if I’m not looking, which of course, is hopeful.

Zibby: Right, I know. I’m going to pretend I’m not looking. I’m going to try to fool myself that I’m not really looking right now.

Cindy: Exactly. I was thinking, though, I might be at the stage where maybe fix-ups are the way to go. There is a new crop of men at this age because people have divorced and died. There was a period where there was no one. Now there’s kind of a new group of men. I feel like maybe fix-ups are the thing to do at this age because everybody comes kind of prescreened. They’ve already been through a relationship your friends know.

Zibby: That’s true. There are a lot of people who do have someone to put on an “in case of emergency” who they can’t stand or that they feel so alone even in a relationship.

Cindy: They’re not sure they’re going to be good in an emergency.

Zibby: They’re like, what are these people — they’re going to shut me off. They’re going to be like, turn this thing off now. Maybe I should pick someone else.

Cindy: I just went through this with my dad. He died this summer. We had a tricky relationship. My sister was his medical power of attorney. Wait, I’m his medical power of attorney. My sister was his financial power of attorney. Anyway, my sister, not so great in this situation. She’s my medical power of attorney. I was like, I think I’m getting a new one after seeing this. She just kept reevaluating and remaking, no matter what, the — my dad, who wasn’t all that happy in life, he said he wanted extraordinary measures taken. She, even though I was in charge, was really like, he wants everything possible done. It was good to have a test run with the person who’s going to be in charge of your plug, to see them around someone else. I was like, you know what? I don’t know. I’m going to, maybe, go with your husband.

Zibby: You have to write that too if you haven’t already. That has to be an essay. Use it.

Cindy: Okay. The new book, in my head at least.

Zibby: That’s so funny. First of all, I’ll set you up if I have the right person. I’m going to be setting you up now that — now my mind is going. Of course, that’s not the point. The point is, you’ve gone through all this stuff. It’s relatable. It’s funny. It’s sad. It’s hard. One time, you’re crying. One time, you’re laughing. That is life. This is it. You’re in it. Your writing just makes everybody feel and feel okay about whatever they’re going through. I’m sorry for all of the stuff that is not pleasant and unbelievable, but thank you for continuing to share.

Cindy: Thank you for what you do. You’ve had so many of my favorite people. In fact, you had Betsy Carter on. She ran — I brought it down — New York Woman magazine. You were probably too young.

Zibby: No, I’m not too young. I’m not too young.

Cindy: She had this magazine. The first piece I ever wrote was one of their back-page essays. It’s in Between Boyfriends, the Only in New York. She published it. That started everything for me. I loved that magazine. It was such a good magazine. It had such good humor. That back page was always Marcelle Clements, really smart female writers who inspired me. I was part of that conversation of, oh, that’s the kind of writing I could do.

Zibby: Betsy Carter is one of the only authors I knew growing up, and so I would always ask her questions. My parents just didn’t know that many writers. When I was trying to write my first novel when I was twenty-five, twenty-six, I would send her drafts. She was so nice to me. Having her on the podcast was such a full circle for me. Now the fact that you wrote for her…

Cindy: I heard you say that on the podcast, how she was part of the reason — I was thinking, she is part of the reason I’m writing too. That article started everything.

Zibby: Oh, my gosh, so funny. Congratulations on all of your work. Thank you for coming on. Thanks for the copies and all of it. Thank you.

Cindy: Thank you.

Zibby: Bye.

WE WAITED FOR YOU: Now We’re a Family by Cindy Chupack

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