This reading group guide for Love at First Like includes an introduction, discussion questions, ideas for enhancing your book club, and a Q&A with author Hannah Orenstein. The suggested questions are intended to help your reading group find new and interesting angles and topics for your discussion. We hope that these ideas will enrich your conversation and increase your enjoyment of the book.

Introduction

In Hannah Orenstein’s Love at First Like, a New York jewelry shop owner accidentally leads her Instagram followers to believe that she’s engaged—and then decides to keep up the ruse.

Eliza Roth and her sister, Sophie, co-own a jewelry shop in Brooklyn. One night, after learning of an ex’s engagement, Eliza accidentally posts a photo of herself wearing a diamond ring on that finger to her Instagram account, beloved by 100,000 followers. Sales skyrocket, press rolls in, and Eliza learns that her personal life is good for business. So she has a choice: continue the scheme or clear up the misunderstanding. With her landlord raising the rent and mounting financial pressure, Eliza sets off to find a fake fiancé.

Fellow entrepreneur Blake seems like the perfect match on paper. And in real life he shows promise, too. But Blake doesn’t know Eliza is “engaged”; Sophie asks Eliza for an impossible sum of money; and feels drawn to someone else—Raj, the bartender down the street.

With a wedding to drum up more business on the horizon, Eliza’s lies begin to spiral out of control, and she’ll have to decide whether to stay engaged online or fall in love in real life.

Topics & Questions for Discussion

1. The novel begins with Eliza’s ex-boyfriend Holden becoming engaged. They’ve been broken up for many years, but she worries that “his engagement means that I’ve officially lost the breakup.” Why do you think this engagement gets under her skin so much?

2. When defending her choice to leave her Instagram photo up, Eliza notes in chapter 2 that there are some female entrepreneurs “whose businesses are bolstered because the founders have enviable lives.” Do you agree with this statement? Can you think of other business owners who have grown their brands by having what seem like interesting personal lives?

3. When Carmen and Eliza look for a potential fake fiancé at Dorrian’s in chapter 3, Carmen describes Eliza’s ideal as “eligible bachelors who would look amazing on Instagram and are dumb enough to not question whatever scheme you’re cooking up.” Do you think Blake meets this criteria?

4. Eliza and Sophie are inspired to open their own business by their parents, who own a boating store in Maine. How do you think opening a small business has changed since the time when their parents did so?

5. How do you think Sophie feels about Eliza being the face of the brand, especially when Sophie worries she may hurt the business in the long run?

6. Eliza’s many Instagram followers are a significant presence in this novel. In chapter 10, she claims that, “It’s good for customers to see that I’m a real person who eats cheese and drinks wine, too. It helps them feel like, you know, they know me. And that translates directly to sales.” How do you think having so many strangers following her life affects her? Is Eliza using Instagram as a tool for promoting her business or as an outlet for herself?

7. When Sophie asks Eliza for a large sum of money for her IVF in chapter 11, she tells Eliza, “You’re getting everything you want.” Do you agree? Why or why not?

8. Eliza wrestles with her feelings for Blake for much of the book, saying in chapter 16, “It’s hard for me to wrap my head around how I feel about Blake. . . . I don’t doubt that I have feelings for him, but I do doubt that they match the strength of his feelings for me.” Do you think her ruse hinders her ability to express her feelings for him?

9. Blake and Raj represent two opposites: the guy who looks good on paper and the guy Eliza’s drawn to in real life. Think about the way her relationships with each progress. How do they differ?

10. Why do you think Eliza keeps Blake in the dark about the fake engagement and wedding for so long?

11. In many ways, Eliza’s ruse picks up steam when she’s offered free or sponsored products for her wedding. Do you think her sponsored wedding is something she would have picked for herself?

12. Sophie and Eliza are very different people, and yet they share a close bond as sisters and business partners. How is this tested throughout the novel?

13. When we talk about dating in the digital age, we often talk about dating apps. How do you think other forms of social media—like Instagram—influence the way we find and fall for partners?

14. At the end of the novel, Eliza turns down Raj’s suggestion she take a photo on her flight in order to “live in the moment.” Months earlier, in chapter 8, she was staging covert vignettes at Blake’s apartment with the hashtag #ElizaFoundHerJewel. What do you think this says about Eliza’s growth throughout the novel?

Enhance Your Book Club

1. Read Hannah Orenstein’s first novel, Playing with Matches with your group. (Did you catch Sasha’s and Caroline’s cameos in Love at First Like?) Think about the differences between these characters and stories.

2. Look up the Instagram profiles of some of the influencers mentioned here, such as @emilywweiss, @leandramcohen, and @whitney. Do you have favorite Instagram influencers you follow? Share them with your friends.

3. Do as Eliza and Carmen and plan a happy hour night out. If you’re in New York, try AOC East, Le Boudoir, or Dorrian’s. If not, visit your favorite local spot or the place where you would most likely find a fake fiancé.

A Conversation with Hannah Orenstein

You last novel, Playing with Matches, was about a matchmaker in her early twenties. This is about a small jewelry shop owner nearing thirty. What was it like to write these two different protagonists?

I started writing Playing with Matches when I was twenty-two. I wanted to create a protagonist who struggled with the same postgrad challenges that I did, like adapting to adulthood, navigating the ways in which old friendships evolve over time, and striving to create a fulfilling career. I loved writing about that exciting, exhausting, exhilarating time. By the time I wrote Love at First Like three years later, I wanted to explore the life of a protagonist who was a little bit more confident in her career and her own capabilities. People say to write what you know; I felt a little older and wiser than I did with my first book, and that helped me find Eliza’s voice.

Stories about fraud or cons—like the Fyre Festival or Anna Delvey—particularly about “influencers,” are popular right now. Why do you think this has become a cultural fascination of ours? Did these kinds of real-life stories help inform Eliza’s?

Yes! I had been playing around with the concept of a jewelry store owner whose lies start to spiral out of control when I first learned about Anna Delvey. The cultural fascination with her story gave me confidence that I was on the right track.

Jewelry is a big part of this novel. How did you come up with the pieces Eliza and Sophie might sell in the store?

I did a lot of research on jewelers like Eliza—people who found big success on Instagram. The jewelry sold at Brooklyn Jewels is inspired by a lot of current trends I’ve seen lately (yellow gold, three-stone settings, pear-shaped diamonds), as well as trends that have been popular for several years now (diamond halos, diamond pavé bands, birthstone jewelry). Eliza’s engagement ring is actually inspired by Meghan Markle’s!

Who was your favorite character to write and why?

I loved getting inside Eliza’s mind. It’s easy to see Instagram influencers and assume their lives are a certain way, so to explore the messy, impulsive, imperfect aspects of her life—all while she maintains a façade of success and perfection—was a really enjoyable challenge for me.

Dating apps aside, how do you think social media affects the way we pair up and settle down?

Social media isn’t important to everyone, but if you do care a lot about it, it can be frustrating when the person you’re dating doesn’t respect your interest. In the grand scheme of things, it’s pretty harmless if you like to photograph your brunch before you dig in, or if you ask your significant other to take a picture together on date night. But anecdotally, I’ve experienced and heard so many stories of men who seem to have really negative opinions of women who love social media. Because of that, it was important to me to include scenes in which Eliza discusses social media with both Blake and Raj, respectively. Blake challenges her interest in it and teases her for it, while Raj later encourages it (in that final moment on the plane).

Raj and Blake are so different from each other. What do you think they represent for Eliza?

Growth! There are a lot of books out there in which the heroine falls in love at first sight. This is not one of them. In real life, dating can be messy and complicated; the process of figuring out who you’re compatible with can be tough. Ultimately, as Eliza gets to know Blake and Raj better, she gets to know herself better. Through the process of dating both men, she learns a lot about the kind of life she’d like to lead. Blake represents the life she feels she’s supposed to want—he’s ambitious and successful, just like she is, though their connection isn’t the strongest. Raj offers her a new way to imagine her life: she can pursue her career with a supportive partner who makes her feel like the best version of herself.

Friendship and sisterhood are big parts of this novel. As people pair off in their late twenties and thirties now, how do you think we rely on these relationships?

Friendship is important at every age, but particularly in your twenties when you’re single. Eliza has different relationships with Sophie and Carmen—one is her sister and one is her best friend—but functionally, they fulfill very similar roles in her life. I liked casting Eliza and Carmen with this dynamic because it’s important to me to celebrate strong friendships in my writing.

Eliza and Carmen have a weekly happy hour date where the location changes each week. In Playing with Matches, Sasha frequents Hotel Tortuga on Fourteenth Street. What’s your go-to spot in New York?

Hotel Tortuga was my go-to spot with my friends for years. The same year that Playing with Matches came out, though, the restaurant was bought by new owners, and I’m sad to say it’s no longer quite the same. Many of the spots in Love at First Like are tributes to places I love dearly in New York—Golden Years and the Wythe Hotel in Williamsburg, and AOC East, Dorrian’s, and Brandy’s on the Upper East Side.

In the last few years, we’ve seen a lot of influencer weddings that are partially if not completely sponsored. Were you thinking of any in particular while you were writing? How do you think these sponsored weddings influence those that are not?

The first time I remember a wedding from an “influencer” type (I’m using that term loosely in this case) is 2014, when #nellandteddy, the Instagram hashtag for Nell Diamond and Ted Wasserman’s wedding, suddenly appeared all over my feed. There’s even a HarpersBazaar.com story from that week with the headline, “The Internet Is in Love with Nell Diamond’s Gorgeous Wedding Photos.” It was one of the first times that wedding photos from a noncelebrity really dominated social media and digital media, and that concept certainly influenced Love at First Like. Just as I finished the first draft of the novel, Brides announced that fashion blogger Chiara Ferragni would appear on the cover of their Weddings of the Year! issue. The fact that an influencer would get that honor—instead of Meghan Markle or any number of high-profile celebrities who got married that year—speaks volumes about how influencer love stories and weddings are a source of cultural fascination right now.

What do you want readers to take away from this story?

My number one goal is always to entertain. If readers have a great time reading about Eliza’s adventures, I’m happy! Beyond that, I hope this novel helps people consider what roles ambition, love, passion, and social media play in their own lives.

What’s next for you? Are you working on anything new?

I’m currently writing a third novel set in the world of elite gymnastics, due out summer 2020 (in time for the Olympics!). I also work as the senior dating editor at Elite Daily, editing stories about single life, dating, and relationships, and I stay busy taste-testing every cheese plate in New York City.