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Strand Book Store Virtual Book Talk with Hannah Orenstein + Becca Freeman: Head Over Heels

The Strand Book Store in New York City, New York hosted a virtual event (on both Zoom and Facebook Live) to celebrate Hannah Orenstein's new novel: Head over Heels. Becca Freeman asked Hannah Orenstein questions about her writing process, the new novel, and her previous experience with writing. After Freeman finished her questions, virtual audience members were able to send in questions. Freeman asked and Orenstien answered beautifully. If you were able to attend the event, please comment about your experience. If you were unable to come, please read the summary of questions and responses, but first, a little about the women and book of the event. 

The People

Hannah Orenstein is the author of three novels: Head over Heels, Love at First Like, and Playing with Matches. By day, Orenstein is the senior dating editor at Elite Daily magazine. By night, her experience editing aids her in writing novels about romance, sports, comedy, and even jewelry...? She has written for a number of newspapers, magazines, and websites including The Washington Post, Cosmopolitan, Marie Claire, Refinery29, Buzzfeed, and Bustle. Her pieces have been picked up by The Boston Globe, The New York Post, The Cut, and Us Weekly. While writing and editing is her calling, she's a speaker and panelist as well. She has appeared on Buzzfeed's AM2DDM, Cheddar, HLN, Fox, Bold TV, Sirius XM radio with You Up w/ Nikki Glaser, At Least You Woke Up with Jill Kargman, and The Michelle Collins Show. She spoke at Her Conference, Jewish Women International, and the JCC. Before the Elite Daily, Orenstein was an editor at Seventeen.com, and at just 21 years old, became the youngest matchmaker at a highly ranked dating service. Hannah Orenstein lives in Brooklyn. 

Becca Freeman is a self-employed, freelance marketing consultant in New York City and a podcast host. Previously the Head of Marketing at LOLA, Freeman has worked with popular brands on their "growth, retention, content, and brand strategies." Some of her clients include: Daily Harvest, Buffy, Birchbox, Parsley Health, Scribd, Henning, Chinese Laundry, and KIND Snacks. Becca Freeman is the Co-Host and Co-Creator of Bad on Paper podcast where "your new internet besties give you a weekly dose of books, banter, and folks you should be following." Freeman's second podcast on which she is a Co-Creator, RomComPods, provides weekly episodes of a 'rom-com' voiced by professional voice actors and actresses and embellished with sounds of the places the characters are in. Honeymoon for One is the first story line the podcast is in the middle of producing. (I have listened to this! It is so good. Check it out on Spotify and other podcast apps.) 


The Book









The Interview
How did the COVID-19 pandemic affect the release of Head Over Heels?
  • Hannah Orenstein reported that the launch was definitely different than those of her other novels; however, this one was not worse. She said that she had a lot more virtual events this time (like the one I tuned into with The Strand!) as opposed to in person signings and promotions. Since the 2020 Summer Olympic Games were postponed, Head Over Heels fills the athletic void for Olympic fans. "Head over Heels is an escapist book," commented Becca Freeman. 
What was Hannah Orenstein's inspiration for the novel?
  • Orenstein was a recreational gymnast for 15 years. "I was never on the Olympic track, though. I'm 5'8"," Orenstien remembers. Hannah Orenstien recounts her participation in gymnastics as one of the best parts of her childhood. It taught her the discipline to write novels. 
What topics did Orenstien have to research even though she has a fairly thorough background in gymnastics?
  • While her personal knowledge of the sport was helpful, Orenstein had to refresh herself on the specific point system, the pressures of competitive/Olympic gymnastics and the Olympic Games and Trials, and the mental and sexual abuse associated with the sport. Orenstien reached out to Olympic gymnasts like Laurie Hernandez and Shawn Johnson for help. Her background in womens' journalism helped her interviews be incredibly detailed. Since she has been the matchmaking/relationships/dating editor of two well known magazines, Orenstein was set to write about both friendship issues and romantic relationships. 
The 'emotional arc' of the main character, Avery, in Head Over Heels is a steep one. What was writing such ups and downs with romance and friendships like?
  • Orenstien's book opens with Avery at her lowest. Her relationship has just been ended. A relationship that had become her entire life after her Olympic journey ended with a traumatic injury and lost friendship. She follows her passion elsewhere to coach a young gymnast. This new job gives her purpose and passion. Avery ends up proud of her growth. Hannah Orenstein said it was hard to write about friends pitted against each other. Unlike her other novels where most main characters have best friends they go to for advice, Avery's long-time friend Jasmine is her competitor and, after her injury, a reminder of her failure. She never wrote about childhood friends who grew apart as they got older because of different choices that changed each woman - until now. 
  • Writing about estranged friends was a reset for Orenstein. There was more loneliness in Avery than any of her other protagonists. Freeman added that Head Over Heels is good for people with lost-touch friendships. Reading about someone you can relate to gives and hope for the future of the character and your situation. 
What was Hannah Orenstien's personal, in-depth history with gymnastics?
  • Hannah Orenstien opened her answer to this question with a description of her favorite leotard. It was red, white, and blue with a firework pattern. Orenstein practiced gymnastics from age 3 to 14. Ally Raisman and Hannah Orenstien grew up in the same town, but Orenstien implied that the comparison, gymnastics wise, stops there. She stopped gymnastics for cheerleading, but quickly quit cheerleading as well because of the time consuming practices.  
What are Hannah Orenstien's favorite rom-com books? What books gave you inspiration?
  • Orenstien loves The Royal We by Heather Cocks and Jennifer Morgan, Red, White, and Royal Blue by Casey McQuiston, and The Idea of You by Robin Lee. 
What advice can Orenstien give beginning authors? What techniques do you use?
  • Hannah Orenstien outlines all of her novels before she writes them. She says this technique helps her get to the meat of her plot and helps her to have a sense of direction for her book. It can also aid her in choosing between ideas. Orenstein had two ideas. She decided to outline both to see which story flowed. She outlined chapters on chapters of one, but the other she could barely make it through. After that, it's clear which idea will be easier and more meaningful to write. Becca Freeman added that for RomComPods, she and her Co-Creator sent out a simple google forms to a handful of their friends and family with a couple ideas they could vote on. When the results came back, they had a clear path to diverge in. When a writer is thinking of ideas, it's easy to get caught up in head-space and brainstorming. When flesh and bone readers are asked about what they would listen to/read, it's easier for an author to pick a direction.
  • Also, take breaks! Orenstein has a full-time job as an editor at the Elite Daily. She mostly writes on weekends, but when she writes on a night after a full day, she likes to take a break between her job and writing. She'll go to dinner with a friend, see a movie, or go for a walk before she sits down with the full intention of writing.
  • Word count also motivates Hannah Orenstein very well; however, sometimes she has too much. Especially when describing settings, Orenstein "goes off." She likes to set a max for herself when writing about settings. Too much description of a place, the reader might get bored. 
What was the timeline for Head Over Heels?
  • Orenstein got the idea in August of 2018. She had the full outline finished by January of 2019. She began writing in March and finished by the closing of 2019. Now, Head Over Heels has been officially released! http://hannahorenstein.com/head-over-heels/
Was writing a sports-romance novel different from other novels?
  • The most different aspect for Orenstein was the centralized setting. The setting was pretty much confined to the gym Avery and her co-characters were in. This makes the senses keener. Also, Orenstein was able to focus on the description of the setting because it was limited to one space. She didn't have to worry so much about excess description. 
Is writing about characters with the same experiences easier? Different experiences?
  • Orenstein remarked that when writing about characters with different experiences than her, it's more like reporting. When the characters have some of the same experiences, the details are easier. Orenstein can get into the characters' heads. She said the processes are different. 
What were the working titles for Head Over Heels?
  • Sticking the Landing was more in the running than another idea: Flipping Out. Orenstein's publishers had problems with the latter title because of its reference to cursing. Orenstein is over all very happy with the title and cover art. (She showed it off during the virtual event quite a bit!)
Lastly, can we expect a new book any time soon?
  • YES! While Orenstein couldn't give much away, she is in the process of writing her next book which is a romance in New York City! Get excited!

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