New York Magazine columnist and author of Apron Anxiety Alyssa Shelasky returns to talk with Zibby about her latest memoir, This Might Be Too Personal. The two discuss misconceptions about writers’ lives, when Alyssa realized her work was famous, and her two remaining regrets after writing this book.


Zibby Owens: Welcome, Alyssa. Thank you so much for coming on “Moms Don’t Have Time to Read Books.”

Alyssa Shelasky: Thank you so much for having me right here sitting on your lap.

Zibby: I know. I’m sorry. I couldn’t figure out how to set up two microphones because it’s been several years since I’ve been doing in-person podcasts. We’re sharing this intimate mic.

Alyssa: Well, that’s the name of the book, Other Intimate Stories, like cuddling with Zibby and doing her podcast.

Zibby: #CuddleFactory. Alyssa, I know I emailed you right after I finished this book, but I loved your book. I fell in love with you as a person. Not in a creepy way. Now I’m touching your knees, so this is even creepier. All of the stuff that you went through and the growth and the hardships and then the ending, you took us through so much stuff, all the stuff of life. Yet you wrote it in such a way that you could digest it quickly. I was flipping through the pages frantically and just wanting more and more and more and so rooting for you. I feel like it will be impossible for anyone to finish this and not just be forever rooting for your success in every way.

Alyssa: Thank you. It’s such a sensitive time when you put a book out. Approval is your oxygen right now. I’m not used to that because I kind of like to move through the world not giving a shit what anybody thinks about me. Then you write a book. You put a book out there. It’s the exact opposite. You just want to know that people liked it. It was a pandemic book in the most unpleasant sense of the word. It was so hard to write it and get it done with my kids at home and no help and all my deadlines and burying friends. I don’t have to tell you. It was the worst time. I wrote this book kind of in — it felt like a fever dream. I don’t even remember a lot of it. I was like, what’s Zibby going to ask me about? I wrote it. I promised myself to tell the truth, to be only myself, and to get it done. That was the extent of the work I did on it. I’m glad to dig in with you because I don’t remember what I said. It’s a pandemic book. It’s raw. It’s honest. There’s tension in there. That’s the reality. That was the reality. Hopefully, it made the book even more authentic because I definitely didn’t have time to obsess over how it made me sound or what I was saying. It was just honest and raw and real.

Zibby: First of all, it’s an exposé on what it’s like when you are a writer and have all these dreams and aspirations and how unstable — instable? — a revenue stream that provides and the things that you had to juggle. We were talking earlier about, there was this whole element of you trying to sell a show. I feel like that was the through line of the thing. You really, from the beginning, wanted to sell a show and all of that, and how you can even put all of your effort towards selling something for TV and then miss out on all the income you might have earned or the projects you would have done and how it’s just so hard to the point where even paying for preschool becomes an impossibility.

Alyssa: There’s this misconception that all these Brooklyn writers, we’re all trust-fund babies or whatever. It’s never been like that for me. Writing is the way I make a living. I’m very practical about the work I take. I have three columns for New York Magazine. I’ve never missed a deadline. I need those jobs. Then like anybody in any job, I’m just trying to climb the ladder and do better and get bigger roles, bigger jobs. It’s a nonstop hustle. Then you’re like, okay, I have my second book and this project in the works and this project, and now I am good. Yet it’s never enough. When do you stop? When is it enough? For me, I would like some financial stability. I think I’ll know when it’s just like, you did it. You’re a success. Go enjoy your kids. Go enjoy the new little house you bought. You did it. I’m not there yet. I’m still sort of clawing to that place. It’s never-ending. It’s tough. There’s worse jobs, for sure, but…

Zibby: It’s just so ironic because anybody on the outside would think, a hundred percent, you’re successful. Are you kidding? This is your second book. You have this new project coming. You have columns. You’ve been a working writer for all this time. I know this is only one sliver of the book.

Alyssa: Thanks. It’s a lot of, also, just our own inner voices. I know that I’ve worked really hard, and it’s paying off. I have a very cool lifestyle because of it. I know that people like my work and like my voice. I do get all of that. There’s just a lot of mental gymnastics when you’re a writer. There’s days where you’re like, everybody loves me. Everyone’s relating to my work. Everything’s happening. I’m going to get a TV show. I’m going to write another book. Then in a flash, you’re like, everybody hates me. Nobody wants to throw me a book party. Oh, my god, why is my book taking up space on this shelf when there’s so many better writers? I just want to hide and be with my kids and never show my face again. I’m unwanted.

Zibby: We are doing our book party together. I’m so excited for that. I can’t wait. It’s in July.

Alyssa: I cannot wait. I thought I was going to have to sleep in my van because I couldn’t find a hotel.

Zibby: Oh, no. Do you want to stay with me?

Alyssa: Heath Freeman hooked me up. Shout-out to his hotels. My point is I would not miss that event for the world. I am so excited.

Zibby: Let’s talk after. One of the other things I loved is your relationship with your mom. We haven’t really explained this whole book. It’s essentially your life journey from a set period of time as you navigate relationships, deciding that the very safe, traditional guy who you were headed toward marriage, that you don’t want that path that so many people happily take and just slide on by. You’re like, that is not my path. You had the self-assurance and will to say, you know what? I’m going to trust my instincts. This is not right. I feel like that’s something you kept doing over and over in the book and your life until you get to a place that is so authentic, but it’s in a different path, perhaps, than other people. You had a baby and then met the love of your life, essentially, which was great. The parts about your relationship with your parents — your mom is the best character in the book. When you go through IVF or you’re doing IUI or something and she’s in the room with you — should we even tell this story?

Alyssa: This is everybody’s favorite scene.

Zibby: Is it? I know. I hate to pick the same thing as other people.

Alyssa: No, I’m thrilled. I love my mom. She’s in all my books. Anything I write, my mom’s always the star of it all. Yeah, I can tell you.

Zibby: I host a sex talk show, so I can say these things now. Tracey has trained me. I can actually say it out loud.

Alyssa: Oh, I write the Sex Diaries column for New York Magazine.

Zibby: I know you do.

Alyssa: I talk about blow jobs and rim jobs. That pays my rent. I had a baby on my own. You’ll all learn why. It was a journey. My mother was really there for me for all of it, as was my father and sister. It was time for the IUI at NYU. The nurse did the turkey baster thing. Then she’s like, “I’m going to leave you in here to get dressed. Get up slowly.” My mom was there with me. She had been super sweet holding my hand and doing her prayers. When the nurse left, my mother starts to move herself into the medicine cabinet, the supply closet. I’m like, “Mom, where are you going?” She said, “Do you have a vibrator?” I was like, “No, I don’t have a vibrator.” She’s like, “You didn’t bring a vibrator?” I said, “No, Mom. Why the fuck would I have a vibrator?” She had read an article that after an IUI, if you stimulate real sex and have an orgasm the way you might during sex, it actually gets things flowing a little bit. She’s just crouched down — you’ll read the rest. It was quite a moment. I didn’t get pregnant that time. I didn’t do the thing she wanted me to do, so maybe my mother was right in the end. Who knows? She usually always is.

About what you were saying before, doing it my way and living an authentic life, I’m so glad you said that. When I was contemplating writing a second book, it was the beginning of the pandemic. I was listening to a ton of podcasts. That’s all I do for my self-care, is walk and listen to podcasts or Audible. I was walking around. I was listening to Brené Brown and Krista Tippett and Glennon Doyle all the time. I love these women. I worship them. I was like, everyone’s talking about vulnerability and authenticity and being your true self, but I actually kind of live my life that way. Maybe instead of just listening to tips and guides on how to do it, maybe I can actually show people what that looks like to a normal person in real life. I started thinking, maybe I can show what it’s like to be vulnerable when you run away from marriage. Maybe I can show what it’s like to be vulnerable at your abortion. Maybe I can show what it’s like to be vulnerable when you decide that you’re ready to have a baby and you are done waiting for a man and you don’t give a shit what anybody else has to say about it. Maybe I can just tell those stories. Nobody’s going to come to me to speak on feminism or women’s theory, but I can share my personal stories and show people what it felt and tasted like and smelled like and how it all played out. Honestly, look, it worked out. It was scary and painful and hard. I had no one telling me which way to turn, but I trusted myself in a real way. It really did work out.

Zibby: That’s so amazing. All these different junctures, I feel like you let us into your decision-making process, even the times where you’re literally trying to sabotage yourself, like when you go to the farm. It’s so perfect with this — I don’t want to give anything away. During this one relationship, you have a time that’s actually really nice and welcome. You don’t even trust it, which I completely relate to. I’m like, this is too good. Something’s wrong. You were like, I don’t think I can do this. It’s just too good.

Alyssa: It’s too good. You walk through life sometimes and you’re just like, everyone’s got it all figured out. They’re all so beautiful. They’re all so in love. They’re all so fertile, or whatever it is that you don’t have at that moment. That’s bullshit. It’s exactly the opposite. Everyone you meet is going through something and is hurting and has been through trauma and pain and is working through it just like you. In that moment, it was a tough spot for me because everyone was just so perfect. I am not that. I am messy. I am flawed. Thank god. I love that about myself, but it’s not always the easiest way to be.

Zibby: Everyone is messy and flawed, is the truth of it. That’s part of what is so amazing about this. You take all the inner stuff and share it. Everyone will relate to some piece of this or another. Oh, yeah, she worries about that. She does that. The way, even, you share heartbreak and relationships that didn’t work out and why and how — I found it so interesting when you loop back around with one of your exes towards the end to find out, what do you think? What did we do? Did I do something to destroy this?

Alyssa: These narratives we tell ourselves, that’s therapy 101. We have these stories. Our inner voices, can they be trusted? I really believe in perspective. When you’re worked up about something or hurting or upset, I try to look at things from every angle. I can say, this is how I feel about it, but this is actually what happened. The two can exist. That’s how I felt with that ex. In my mind, I wrecked everything. I burned us down. I destroyed it. I’m a nightmare. Is that true? He was like, “No. Hell no.” Maybe he was just being generous. It’s interesting.

Zibby: The only story that I wanted that was not in here was the story of this book selling and you getting this book deal. I feel like we were along for the ride for so many ups and downs. Then you just mention at some point, and then I got the second book. Then you’re so funny. You’re like, hi, in parentheses. I was like, that’s so funny. I love that. Then you just kept going. When did that happen? How did that happen? This is not a criticism. I’m not saying you should’ve put it in the book or anything. I’m just saying I was left wanting more. That’s all.

Alyssa: Good. That’s great. It happened because I got so busy raising my kids and making a living as a freelance writer that I didn’t realize my work was kind of popular. You’re in the grind. You’re making your deadlines and strumming up new assignments. I just didn’t really realize until I wrote that article for The New York Times called “For Parents, Sex is Dead” or “RIP Sex” or something. The feedback was unbelievable. It went viral. That article, for me, was something I just wrote in a second probably from the subway. I just put it out there into the world. Because the feedback was so nice, I was just like, oh, I should be doing more. I should write a second book. People like what I have to say. More than that, it’s making people happy and feel less alone. It’s easy for me to open up like that. It’s very easy for me to talk about sex and heartbreak and misadventures of the heart. I called my agent, Meg Thompson. I was like, “Do you think I have another book in me?” At the same time, she knew — again, I was oblivious to the fact that my Sex Diaries column for New York Magazine had become a really big deal. There was TV networks interested in it. We were just like, “Oh, yeah, you’re having a moment.” I didn’t even realize because I just was too busy surviving. Something was happening. I decided to run with it. I always knew for the second book I would know when the time was right. I was like, it’s now. Let’s go. Let’s do it. I pitched this book to St. Martin’s Press. That’s who I wanted. My editor, Hannah Phillips, took it from there and made it all come to life. It’s been a really, really positive experience. I loved it. I can’t wait to write my third.

Zibby: Awesome. I can’t wait to read your third.

Alyssa: You’ve got the bug too.

Zibby: How are you handling the people who you write about in this story?

Alyssa: That’s the problem. The best writers, I feel like you have to just not care. You just can’t care about making people mad or getting upset with you. You can’t care about getting sued. You just have to be like, fuck it. I’m an artist. I’m going to write what I want. I’m not that person.

Zibby: I was like, go, Alyssa. You got this.

Alyssa: In every other way — we don’t know each other that well socially, but in my personal life, I am very tough. Don’t come for me. Don’t come for my kids. I’m pretty fierce. I’m my mother’s daughter. I’m very fierce and strong. When it comes to my books and my work, I don’t want to get into any trouble. Again, this is my livelihood, so it’s tricky. There’s a lot more I would’ve said, of course. I’m not going to pretend. There are details I would’ve loved to share with the world, but I’m afraid to hurt people I love. I’m afraid to lose work, whatever. I try and tell the truth. I try to keep it positive because most of the people in my life, I am madly in love with. Beyond that, I check almost everything with everybody. I do the best I can. Then I have really good lawyers.

Zibby: That’s all you can do.

Alyssa: That’s all you can do. If you’re going to be afraid, you can’t call yourself a writer. You can’t. It won’t work, or at least a memoirist. Writing a novel would be great because I can just explore all of this and go as deep and dark and dirty as I want to be.

Zibby: That could be your next thing.

Alyssa: I know. It would be like becoming a surgeon, though. It’s a completely different art form, I feel like.

Zibby: I don’t know.

Alyssa: No? I don’t know.

Zibby: I don’t know. I bet you’d be really good at it.

Alyssa: There’s a lot that would be fun to release.

Zibby: All the stuff you wish you had —

Alyssa: — Yeah.

Zibby: What about your kids? I know other people often say, how do you write about your kids? Are they characters? How do you handle that in literature? Not just in the book, but even in your life, you’re very open about who your kids are and posting and whatever. Did you make that decision at some point and say, this is great, this is who we are? What are your thoughts about that?

Alyssa: I’m a really open person. That’s who I am. I haven’t really had a heavy conversation with myself about it yet. I sort of say to myself before I write something or post something, is this something I would say at a dinner party? Is this something I would share at a work lunch with my colleagues? If the answer is yes, then I’m okay with it. As far as my daughter’s creation story and the sperm donor and the anonymity of him, I felt more protective of him, in a way, because that’s the unspoken deal. I don’t know who he is. That’s the unspoken deal we have, is that he will remain anonymous. I have to respect that. I love this man. He gave me the greatest gift of my life, my daughter. I was protective of the few details I know about him. I do just think I have good sense of what’s okay and what’s not. My kids are still young. My daughter’s six. My son’s two. I’m sure things will change and it will become a little bit more complicated. For now, I just trust myself as a mother. I know what I’m comfortable with. I can leave it at that.

Zibby: That’s such an interesting thing, to love someone and be so grateful to someone you’ve never met and perhaps will not meet. Who knows? We’ll see what happens. He could just be walking past you, sitting next to you on the subway. Do you look at everybody around ever and think — I know you had the one thing where you thought maybe that was him.

Alyssa: There’s a scene in the book where — donors get celebrity lookalikes. I call him Vince Vaughn. I disguised that because if you were to go to California Cryobank, that would’ve been too revealing. It was an actor like Vince Vaughn. I thought I saw him in real life in LA. I was like, this is the moment. What do you say? For me, I’m never speechless, but I was speechless because I was almost positive this was the sperm donor just based on who I would imagine he would grow up to be. I’ve only seen childhood photos. First of all, I was frozen. I just couldn’t move. I was in a state of shock. Also, I made this quick mental calculation that it was better he remained a mysterious superhero to me. It was better he remained a fantasy. I didn’t want to know that he was going to his job at Home Depot and then to choir practice. Who knows? All that would’ve been great. No judgement, but I don’t want those details. I just want him to be this angel — gorgeous, with great genes, really healthy DNA — angel who helped me get pregnant. I can leave it at that.

Zibby: That’s amazing. I even love how you, at one point in the story, you’re trying to figure out — you’re like, I feel like something’s coming next. I feel like I’m getting this vibe. Then all of a sudden, oh, it’s motherhood. That’s what I want to do next. I just know it now a hundred percent. I’ve identified it. Now I’m doing it.

Alyssa: I’m so glad that my parents raised me or — who knows? I was born with the sense to grab that. When you know something to be so true, I just grabbed it. I was not letting go of it. I was convinced now is the time. I meet so many women now who are just trying it on for size. Maybe I’ll become a single mom, or whatever. I’ll see it. Then I’m like, they’re not ready to grab it. Anyone, beware of me if you want to have a baby and you’re not sure how because I will get you pregnant. I am relentless. It was the best decision ever. Granted, I had a built-in support system, tons of family. I never had a nanny, but I had my mother, my father, and tons of friends. If you want to be a mom and you know that for sure, you have to make it happen. It’s too tragic otherwise. There’s so many ways. Somebody once said to me when I was trying to get pregnant, “I never met a woman who wanted to become a mother and didn’t find a way how.” There’s ways. There’s hope.

Zibby: There are lots of ways to be a mother too.

Alyssa: Exactly, many definitions. There’s lots of hope.

Zibby: You’re from a Jewish family. I feel like your Judaism also played a role as one of the themes in the book. Talk a little more about that and how it plays into your life now.

Alyssa: Thanks. It’s so funny. When we were talking about press for the book, they were like, “How about Vogue? Hopefully, we’ll get Zibby.” I was like, “What about Boston Jewish Life?” I don’t even know if that’s a magazine. Of course, 92nd Street Y. I really felt like this book had such a Jewish soul. I rejected my Jewishness for many years. I never cared about marrying a Jewish guy. I still have never had pork or shellfish, which is shocking considering I had a baby with a Lebanese sperm donor. Being Jewish is a lot about contradictions. I’ve embraced those contradictions. All I can say is when I got pregnant with Hazel, the Jewish community, the Chabad, not to be preachy or whatever because it’s not for everyone, but they were really there for me in so many ways without wanting anything back. It meant a lot to me. When I was about to become a single mom, the people that lifted me up and supported me, I will never forget. I will never forget my friend Heather who left me a homemade jar of lentil soup the day I came home from the hospital; my friend Danielle, I mention her a million times in the book, who bought me a fancy Oeuf crib. This was almost seven years ago. I will never forget these things. It’s important to hold onto. That’s the stuff that matters.

Zibby: You give me goosebumps. It’s true. Sometimes the people you least expect come forward in times of need. You’re like, oh, my gosh, that’s so nice.

Alyssa: A hundred percent. Oh, my god, absolutely. I talk a lot about — I don’t talk a lot about it. I’m the opposite of a class mom or the opposite of a PTA mom. I’m busy. I’m disorganized. My kids never show up with the right T-shirt for the right event. I’m always like, oh, PTA moms… Then recently, somebody who is very involved in my daughter’s school asked me for coffee. I was like, oh, she’s going to want me to write something for them. I was like, “Okay, but I have a hard out in twenty minutes. Very important.” She was like, “We just wanted to throw you a book party. We just wanted to have an event for you. We want to pay for it. We found a place. They’re in.” I was moved to tears. Here I am judging all these supermoms because I feel like I’m not one. They were just there to show up for me. It does come from unexpected places. I have so much gratitude. I’m not just using the word. It fills my heart.

Zibby: I love that so much. What kind of books do you like to read?

Alyssa: I’m an Audible whore. I just went on a real Taylor Jenkins Reid binge. I did it all backwards because god forbid I do anything the normal way. I did Malibu Rising, Daisy Jones — I loved Daisy Jones so much; I can barely talk about it without starting to quiver — and then the Evelyn one. Molly Shannon’s book, have you started it yet?

Zibby: No. I have it right here.

Alyssa: Do it on Audible so you can hear her voice.

Zibby: Okay, I will. That’s a great idea.

Alyssa: It is so good. Zibby, I’m not saying that because we’re friends. It is so good. It’s so heartbreaking. It’s so funny. Everybody says that about every single book, but this one is truly a combination of —

Zibby: — I didn’t realize she had such trauma in her life early and all of that until I was reading all the reviews and everything.

Alyssa: I just texted my friend, the friend I know Molly from. I was like, “Am I going to die at the end of this book? Is it going to break my heart? Is it going to destroy me?” She’s like, “You’re going to cry.” I said, okay, I’m going to wait until I put my book out, until I get through all this. I don’t think I can handle just crumbling to the ground in Brooklyn Heights sobbing right now. I’m fragile enough. That’s sort of the genre. I’ll read Jessi Klein’s book. I’m sure I’ll love it and hate it because I want to be her so bad. I love your books. I just got it, as you know, so I haven’t got too far. It’s right in my wheelhouse.

Zibby: Thank you. I do feel like there are similarities to our stories in some ways, like setbacks and writing and trying to accomplish something and obstacles and books. Maybe it’s more like what I know in my head that maybe is not even in the book. You know what I mean?

Alyssa: Right. I feel like I pick up on it. I get what you’re saying. There’s a reason. We wouldn’t be here today in your living room touching knees if we didn’t feel a certain sense of closeness.

Zibby: I promise I will set the second microphone up soon.

Alyssa: No, it’s great. It’s great. This is real down-to-earth, gritty podcasting on the Upper East Side.

Zibby: This is how I’ve been doing it the whole time. You’re like, I thought you’d have equipment and be prepared.

Alyssa: Where’s my headset? Where’s my assistant? Where’s my Pellegrino?

Zibby: No, no, no. I literally plug in the one I bought on Amazon from day one. This is how I still do it.

Alyssa: I love it. It’s good. It’s you. I actually want to say, I only have two regrets about the book. One, that I called Jake Gyllenhaal an asshole.

Zibby: I did notice that. I was surprised by that. I hadn’t heard that.

Alyssa: I’m not saying it’s not true. It came out so harsh. I see his sister almost every day in my neighborhood. I want to be her friend, but I also don’t want her to find out that I’m the one who called her brother an asshole. I’m avoiding her. The second one is, I wish I had declared my love for you somewhere in the book.

Zibby: Me? Oh, my god, stop.

Alyssa: I wouldn’t dedicate the book to you.

Zibby: Oh, my gosh, you’re so funny.

Alyssa: We got closer. You started supporting this book in particular after it was all said and done and at the printer and everything.

Zibby: Do not even think twice about it.

Alyssa: I know you don’t care. I know you care zero. You have, to me, been part of this journey. I will dedicate my third book to you. I know you would die.

Zibby: I would die.

Alyssa: That is not your style. I just wanted to say that.

Zibby: Aw, you’re so sweet. That’s really nice.

Alyssa: You and Jake Gyllenhaal in the same sentence.

Zibby: Thank you. Two regrets, Jake and me. What advice do you have for aspiring authors?

Alyssa: Oh, god. What can I say that hasn’t been said before? Again, I’m not the kind of author that’s like, go deep into the woods and find your inner soul. I’m a, get an internship. Work your ass off. Make a million contacts. Prove yourself to be invaluable. Do good work. Never miss a deadline. Hustle. Email an editor back a hundred times in a row if they’re too busy to get back to you. That’s the kind of advice I would give. Just push hard. Fight for yourself. Advocate for yourself. Assert yourself. No editor or agent or whatever is going to begrudge you for being too confident or too aggressive or too hungry. It’s a beautiful thing. Just go for it with everything.

Zibby: I love that. Thank you, Alyssa. This was so fun.

Alyssa: Thank you so much.

Zibby: Congratulations. I can’t wait to see it come out in the world and all the exciting things to follow.

Alyssa: Thank you. Me too.



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