How a rom-com author rewrote her happy ending after a breakup
Hannah Orenstein's new novel, Head Over Heels, follows a former pro-gymnast starting a new life after her relationship ends
Author Hannah Orenstein has had a year. Her third novel, Head Over Heels—about a former Olympic-hopeful gymnast named Avery who gets dumped and starts a new life as a gymnastics coach in her hometown—is out today. A few months ago, coronavirus arrived and Orenstein moved in with her parents and sister outside of Boston to quarantine. And in November, the boyfriend she was living with in New York City suddenly broke up with her—right in the middle of the monthlong window she was supposed to spend editing her book. Orenstein had to figure out how to mourn a relationship and rebuild her life while summoning the strength to put the final touches on her novel. But as she healed she discovered her own resilience, and found that her experiences helped her insert details into Avery’s storyline that made the book more realistic and relatable.
I spoke with Orenstein about writing three books in three years, how working as a matchmaker in her early twenties launched her career, and why we should change how we think about happy endings.
We need to talk
Jillian Anthony: When did your breakup happen?
Hannah Orenstein: It happened just before Thanksgiving.
It’s been a good chunk of time. How are you feeling now?
You know, I feel good. When it first happened a lot of my friends said to me, “This is just going to suck until it doesn’t,” and I think I’m at the point now where it doesn’t suck. For a long time I couldn’t see that coming but now it’s here, which is nice.
I’m so glad to hear that.
Thank you. How are you doing?
I am much, much better. It’s funny you said you’re feeling better now, because even with the pandemic and being laid off and everything going on, I totally relate to that. I would take where I am now over where I was about eight months ago any day. Were you still finishing Head Over Heels while you were recovering from your breakup or was that already a done deal?
I was in the middle of editing this book. The first draft was completely written and I had a couple weeks to turn it around and finish the second draft. It was a really emotionally intense time. I was hoping that those weeks would be purely dedicated to working on the book, and then suddenly I had a lot of other things going on in my life. But I think that pushed me to sharpen some of the scenes that follow the breakup in the book. It forced me to reconsider how Avery might move through the world and what her thought process might be like. For Avery the breakup really lit a fire under her butt and made her chase her ambition in more powerful ways than she ever would have before. And I don’t know if I would have been able to see that so clearly if I hadn’t been in a similar situation. I added a brief scene toward the end of the novel in which Tyler [Avery’s ex-boyfriend] reaches back out to Avery months after he broke up with her and, without giving away too much, I will say that scene was just delicious to write. In that moment you see how intensely Avery has grown.
I just love how [his text message] comes on one of the most important days of her new life, because that’s always the way it is. They will come back at the goddamn second that you’re feeling okay or that you have a really important day. I love that she was able to take it in stride and just move on, and I think that would be a really hard thing to do. So props to Avery.
Thank you. Maybe that’s not the most realistic way that every person on the planet would handle it, but that’s sort of the way I think about a Lizzo song. Nobody’s actually as strong as Lizzo when they are getting broken up with. Lizzo makes it sound like this really magical, empowering experience and I wanted a little bit of that energy in that scene.
Did that situation happen to you?
A previous ex repeatedly contacted me for years after we broke up, even after I asked him to stop. It was very frustrating. I don’t think I ever handled it quite as perfectly as Avery does in that scene but I always wished that I could.
I only wish that I could handle things with that much grace too. Avery [leaves LA and] moves back in with her parents [in Massachusetts] and goes complete no contact [with her ex], which I also think is something few people are able to achieve. What are your thoughts about writing that in, and where do you lie on the spectrum of no contact?
I had a relationship in college that was very on-again, off-again and very messy and we were in constant contact, and that caused a lot of pain and heartbreak and stress. So after I had that experience I thought, okay, once a door closes it’s closed and I’m never opening it again. That’s something that feels second-nature now as an instinct because I know how terrible that experience was. I really did want Avery’s [previous] life in LA to feel like this separate chapter. She hoped LA would be a fresh start because she had built her entire life around the pursuit of making the Olympics while training in her Massachusetts hometown, and when that rug gets pulled out from under her and she doesn’t make the Olympics and she has this really devastating injury, she is floundering for years. She tries LA, she tries college, she tries partying, and eventually the only thing that she can really latch onto for her new identity is her relationship with Tyler. She builds her entire identity around him.
And her new identity [in Massachusetts] is built on her talents, what she enjoys doing, and really starting from scratch.
Yeah, completely. It’s a fresh start.
I was looking back on all you’ve done; you have a job at Elite Daily now, you used to be at Seventeen, you were a matchmaker in your early twenties, and you’ve written three novels in three years, which is incredible. A lot of what you’ve done career-wise revolves around writing about dating, sex, and relationships. Are you building things off of your own experiences?
Yes, to an extent. I fell into this world because when I was in college I interned for Elle and I did a project with E. Jean Carroll, who was a columnist at the time. She was such an idol of mine. I moved to New York to be a writer because I love her career so much. I knew that she had just launched this matchmaking company and I said, I will basically do anything if I can work for her. I had done some matchmaking in college just setting up some friends and writing about the experience. I reached out to her and told her about that and she hired me on the spot. That really kicked off the rest of my career because it led to writing about dating and relationships and sexual health for seventeen.com. I found that I was really passionate about writing about sexual health for teenagers, especially during a time when only 13 states required sex ed to be medically accurate, which is insane. From there I transitioned to writing about dating and relationships and sex at Elite Daily and editing stories about that content. My matchmaking experience was my first novel, Playing with Matches, which is about a matchmaker in New York City who is completely in over her head with a sort of on-again, off-again ex, and you can see where all that came from. I’ve always found it interesting seeing—first as a matchmaker and then a writer and editor—all the different ways that people look for love or try to find meaning in relationships.
How did you go about creating the worlds of your novels?
For Head Over Heels, I was a gymnast for 15 years so that was a world that I knew really well.
Do you feel like you experienced some of that mental exhaustion and physical perfection that [the athletes go through in] the book as well?
I was not on the Olympic track so I really did not experience that extent of it. I was just a kid competing in local meets for high school competitions. I had the nicest, most supportive coaches in the world and they were safe and they encouraged us to be really healthy, but even so, I think I felt this sense of, I can only have this in my life for so long. I’m going to be too tall or too heavy or too old one day and I won’t be able to do this anymore. So I really did try to make the most of it and that meant practicing and competing when I was injured, when I had a stress fracture in my back, when I had two sprained ankles, when I hadn’t really eaten that much that day and I felt really dizzy. I pushed through all of that. I still have chronic back pain as a result, but in the grand scheme of things I’m very much unscathed by my experiences. But I can only imagine how much worse that would be if you’re training at the Olympic level.
A plot in the book also explores sexual assault from these girls’ doctor that people trusted, a doctor that did these things while the parents were in the room. Obviously some of this was drawn from real-life situations. Why was that was important for you to include and explore in this story?
I wanted to write a celebration of gymnastics because it’s a world that’s given me so much, but I can’t do that without also really interrogating the ways the sport has failed young women and girls. So that includes sexual abuse, emotional abuse, mental health issues including eating disorders. I wanted to honor the gymnasts that I look up to so much and that does mean showing the full scope of what this sport does. I started writing this a year after the Larry Nassar trial. He’s serving a minimum of 300 years in state and federal prison after 156 women testified against him, on accusations that are based back to at least 1992, and those are only the ones we know about. The sport is set up in ways that really undermine girls’ and women’s safety, so that was really important to me to show that that’s not okay, and that the system needs to change.
What was that process like for you as a writer?
I wanted to be really sensitive because this isn’t just fiction. It’s heavily based on a real situation. I met a lot of the girls through my work, especially at Seventeen and other publications. I’ve interviewed a lot of these gymnasts and they’re the most lovely, wonderful people in the world. I really wanted to do their stories justice. I’ve worked with groups including RAINN and the National Domestic Violence Hotline and the National Eating Disorders Association, and those conversations really informed the discussions surrounding sexual abuse, emotional abuse, disordered eating, body image issues, and mental health.
It was fascinating to look into what that world is like. At the end of the book Avery says, “But the funny thing about your dream coming true is it never quite happens the way you think it will. There’s always a twist.” That resonates with me because that’s a lesson I’ve learned over the past year—that you cannot hold on to things too tightly because they’ll almost never work out the way you hope. It’s been a lot for me to let go of a relationship that I was happy in and to understand that that didn’t work out, but there’s something else for me. Has that been part of your process over this year too?
Absolutely. I’ve looked forward to this date, June 2020, for a long time and I thought that I would be promoting this book at a series of bookstore events and parties, surrounded by loved ones, including my boyfriend, meeting readers and signing books, and at the end of the night going back home to my apartment in Brooklyn that I shared with my partner. And instead I’m living with my parents in the middle of a pandemic and hosting all of my events over Zoom. If you told me this a year ago I would have thought you were high on something. But this is how it is. Strangely, you can be really happy anyway. There’s an Elizabeth Gilbert quote that I really like. She basically says that if she had seen some of the pain that was coming her way she would have run off and hid in a cave, but she’s glad she lived through it the way that she did because she’s learned she is resilient and she can still find happiness. I think that applies to breakups, to whatever goals you’re chasing. It’s okay if they don’t come through exactly the way that you had hoped because maybe something better is going to come along. I think that applies to this pandemic. I never thought that I would write books. I thought I wasn’t interested in writing fiction, that I didn’t have the work ethic to complete a novel. And here I am.
Are there specific tools that have been really helpful to you to keep moving forward?
I started going to therapy and it’s something that I’ve never done before, and I’m really glad that I tried it. I think time is the most helpful thing and that sucks to hear when you’re in the midst of something really terrible. The other thing I got really into is this app InsightTimer which is a free meditation app.
I too was in therapy and used InsightTimer. I wish I had learned to meditate before I desperately needed its help. I struggle deeply with thought and attention control, and when you’re mourning you need those skills so badly. I’m trying to work meditation back into my life because I know that more grief is coming for me, and I’m hoping that next time I’ll be more prepared to deal with it.
I wish I had more creative and fresh advice but…
I think that the basics really do help. Eating well, sleeping well, doing things you enjoy, meditating, and exercising. The basics will eventually change your life.
I think we are all more resilient than we give ourselves credit for and that’s something that this experience definitely taught me.
You write rom-coms, some of them with traditionally happy endings. You had a romance that you really loved and believed in, and I felt that way about mine. If you were writing a book about that chapter, it might have ended there. When I think about happy endings now I think about so much more, because I know better. Relationships can be really good for a long time and they can still end; there’s just no guarantees about anything. How do you think about your own love stories, and the possibility for more in your life?
I just turned 27. I have many, many more years ahead of me, hopefully full of happiness in many different forms, and I don’t want to take anything for granted but I would hope that there is more to my story. Currently in the middle of a pandemic with my parents in the next room, trying to go on FaceTime dates, and the Wifi keeps cutting out—it’s not the most romantic I’ve ever felt in my life, believe it or not. But of course I believe there’s more out there. It would be really easy to go through an experience like what I went through or what you went through and say, oh, romance is dead, and I don’t want to try again. But it makes me want to try more because now I know how great relationships could be.
What was your grief timeline like and what did you experience?
The first few weeks it just didn’t feel real. I felt like I stepped into an alternate timeline. And then there was a period of time where I was consumed by the logistical details of, did I have to move, where I was going to live, things like that. I threw myself into social plans and figured, if I’m really distracted by going out to dinner with a different friend every night I won’t have time to sit at home and dwell about what’s going on. So I spent about a month doing that. Then I spent the next month feeling exhausted by all my dinner plans and not going out. And then the pandemic hit. I think by that point it was kind of like, oh, haha, you thought you were going through some shit? Well, guess what? There’s more to come. But shortly before the pandemic hit I felt like I was back to myself again, so when it did hit I almost felt somewhat calm knowing, oh, I am resilient, I can handle things upending my entire life. I did it once before.
I completely agree. This year my friend Sam broke up with her fiancé, moved away, moved in with her parents—her attitude when the pandemic hit was like, “Yeah, bring it on! Let’s ruin my whole life this year!”
Good for her.
It’s like, another tragedy? Alright! Let’s do this while we’re still dealing with the other one.
Hannah Orenstein is the author of Head Over Heels, a rom-com set in the world of elite gymnastics that has been named a best book of the season by O, The Oprah Magazine, Cosmopolitan, Marie Claire, Bustle, PopSugar, and more. She’s also the author of Playing with Matches and Love at First Like, as well as the Senior Dating Editor at Elite Daily. Previously, she worked as a writer and editor for Seventeen.com and was the youngest matchmaker at the nation’s largest dating service. She’s on Instagram and Twitter at @hannahorens.
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