Success Story Interview - Hannah Orenstein

An Interview with Hannah Orenstein (stalkingagents on QT) upon receiving an offer of representation from agent Allison Hunter of Trellis Literary Management.


QT: Can you tell us a little bit about the book for which you've found representation? What inspired you to write it?
Hannah Orenstein:
PLAYING WITH MATCHES (Touchstone, 2018) is a workplace comedy about Sasha Goldberg, a 22-year-old professional matchmaker for an elite dating service in New York City. Sasha trolls for pedigreed catches on Tinder, coaches her clients through rejection and heartbreak, and dishes out dating advice to people twice her age. She quickly learns that balancing the demands of her quirky clients with her own messy personal life is tougher than she expected.

Believe it or not, I actually worked as a matchmaker for an elite dating service in New York City when I was 21. I couldn't not write about it. How do you pass up an opportunity like that?!
QT: How long have you been writing?
Hannah Orenstein:
Since preschool? Kindergarten? Something like that.
QT: How long have you been working on this book?
Hannah Orenstein:
A little more than two years. I wrote a short story about a young matchmaker in February 2015. Right away, I knew I wanted to try expanding it into a novel, but I didn't have time while I was finishing up college. I couldn't let go of the idea, though, so I spent that spring obsessing over characters and plot twists and how I'd string the whole novel together.

I began my first draft in May 2015, right after graduation, and I felt ready to query agents by July 2016. I signed with my amazing agent, Allison Hunter from Janklow & Nesbit Associates, five weeks later. We did two revisions of the manuscript before going out on submission, and in February 2017, my brilliant editor Kaitlin Olson (at Touchstone, a Simon & Schuster imprint) offered me a deal. I just sent her my final draft two days ago (July 2017).
QT: Was there ever a time you felt like giving up, and what helped you to stay on course?
Hannah Orenstein:
Yes, totally! I finished my first draft right before Halloween and intended to put it away until the new year. I wanted to be able to see the manuscript with fresh eyes. I was confident the first draft was pretty killer. But when I picked it back up, I was totally horrified. I hated it. And that made it really tough to get back into the swing of editing, revising, and rewriting. I was very mopey about it. That March, my mom was like, "Oh my god, just edit the book already." And I did. Moms are wise. Listen to them.
QT: Is this your first book?
Hannah Orenstein:
QT: Do you have any formal writing training?
Hannah Orenstein:
I have a B.A. in journalism and history from NYU. I also took two fiction workshops and two narrative non-fiction classes in college that helped enormously.
QT: Do you follow a writing routine or schedule?
Hannah Orenstein:
It took me two months after I graduated college to land a job, which wasn't amazing in terms of paying rent or my self-esteem, but happened to give me a lot of time to write my book. I liked to work out of coffee shops during weekday afternoons. Later, once I was employed, I preferred to write on weekends and during vacations. I'm a writer and editor at, so it's tough to write and edit all day at the office and then come home to do more of the same thing.
QT: How many times did you re-write/edit your book?
Hannah Orenstein:
Three or four drafts before I queried, two with my agent, two with my editor.
QT: Did you have beta readers for your book?
Hannah Orenstein:
I sent every chapter to my little sister as I wrote them. She was 17 at the time and my biggest cheerleader. My parents both served as incredibly helpful beta readers, and a couple friends read occasional chapter here and there and offered feedback. But I didn't join an official critique group.
QT: Did you outline your book, or do you write from the hip?
Hannah Orenstein:
I'm a slave to outlines. Writing is SO TIME-CONSUMING. I'm terrified of spending months working on a plot arc or a character that doesn't pan out!
QT: How long have you been querying for this book? Other books?
Hannah Orenstein:
I was really lucky. It took me five weeks.
QT: About how many query letters did you send out for this book?
Hannah Orenstein:
I sent about 25 query letters and kept track of them all in a really intense, color-coded spreadsheet. I was so nervous and neurotic about it. I couldn't sleep. I found that fiddling with the spreadsheet gave me a certain amount of busy work to do that helped distract me from thinking, "Oh my god, the same agent that works with [author I'm obsessed with] could be reading my query RIGHT NOW." I also stalked every agent on Twitter and Instagram, read every Google result they had, and generally turned into a nut.
QT: On what criteria did you select the agents you queried?
Hannah Orenstein:
I used Manuscript Wishlist to find agents who represented women's fiction. Beyond that, I read agents' bios and social media platforms and tried to determine which agents felt like they might be a good fit for my work. I also looked up agents that represented my favorite books. I had heard the author-agent relationship described as almost like a marriage, so I knew I wanted to work with someone I clicked with.

I wound up with three offers for representation. I really liked each agent and I'm so thrilled to have signed with Allison. Her assistant passed along my query, then asked me for a partial manuscript, and then the full. Allison emailed me late on a Sunday night to offer me representation. (Full disclosure: Almost a year later, I can still recite that email by heart.) We're both in New York, so we met up that week for a drink to discuss her vision for the book. I was blown away that she came prepared with a list of ideas, suggestions, edits, and a dozen editors she wanted to pitch. Allison has worked with so many writers I admire and I immediately knew that she would be the perfect person to represent my writing!

Editing and submitting your book can be even more stressful than querying. Allison has always kept me in the loop, answered my zillions of questions, and calmed me down when I panicked. I love her.
QT: Did you tailor each query to the specific agent, and if so, how?
Hannah Orenstein:
I tailored most of my intro paragraphs. I figured if I could catch an agent's attention right away, they were more likely to read the rest of my query closely. If they worked with an author whose book I just read, I noted that. If they went to college in my hometown, I noted that. If they mentioned on Manuscript Wishlist that they had a specific interest I happened to share, I noted that. I tried to give each letter a personal touch.
QT: What advice would you give other writers seeking agents?
Hannah Orenstein:
I know it can be really tempting to query the minute you finish your first draft, but I'd suggest waiting until your manuscript is in the best shape possible. I had family and friends read it and give me feedback, overhauled the manuscript with revisions, and wound up querying about nine months after I finished my first draft. I'm glad I waited.

The query process can be stressful, but it will not kill you. I promise. If you're freaking out, just try to stay as busy as possible. Go outside! Hang out with friends! Work on a second book! Don't stare your inbox, willing an email to appear.
QT: Would you be willing to share your query with us?
Hannah Orenstein:
Sure! I decided to pitch Allison after I read and loved her client's book that revolves around an advice column. Advice columns happened to play a big role in my life and, in a roundabout way, led me to work as a matchmaker and ultimately write my book.

Query Letter:

Hi Allison,

I just devoured Katie Heaney's Dear Emma and had to send you an email. My obsession with advice columns stretches back to high school, when I treated E. Jean Carroll's advice column in ELLE like a religion. It wasn't until I moved to New York that I learned about E. Jean's side business running a matchmaking service. I didn't think she'd hire me, since I was still just a college kid, but I was bowled over when she decided to bring me on board. I wasn't confident in my matchmaking skills, but I figured at least I'd get some writing material out of the job. And oh, boy, did I ever.

I have a completed 84,000-word commercial women's fiction manuscript titled Swipe Right for Bliss. It's inspired by my real-life experiences working as a matchmaker for the dating service Tawkify in 2014 (you can read more about my matchmaking adventures at Refinery29). The first 10 pages of my manuscript are below my signature.

Sasha Goldberg, the 22-year-old daughter of a Russian mail-order bride, embarks on a career as a matchmaker for New York City's elite at the dating service Bliss. She trolls for pedigreed catches on Tinder, coaches her clients through rejection and heartbreak, and dishes out dating advice to people twice her age. She hopes her clients find The One — like she did in college with her finance bro boyfriend Jonathan Colton — or else her dwindling income will force her back to her mom's place in New Jersey. But when Sasha discovers that Jonathan is cheating on her, she spirals out of control... and right into the arms of Adam Rubin, the writer with the sexy Southern drawl she had set up with a Bliss client. He's strictly off-limits, but she can't help but fall for him. How will she pursue what's in her heart without jeopardizing her job?

I have more than five years of professional writing experience, including my current position as a features and news writer at My work also frequently appears on,,, Refinery29, Bustle, and more. I speak about writing at annual conferences including the Her Campus Conference, the Lady Project Summit, and the Smart Girls Conference. My platform includes 3,000 followers on my personal Twitter (@hannahorens) and 15,000 on my Gossip Girl-inspired parody Twitter (@modern_gg). I studied journalism and history at NYU.

The first 10 pages of my manuscript and a synopsis are below my signature. I can be reached at [redacted] or by phone at [redacted]. Thank you so much for your time!


Hannah Orenstein