In ‘Planning Perfect,’ an Asexual Jewish Heroine Gets a Dreamy Queer Romance

Author Haley Neil tells Hey Alma that her new novel grew out of a joke about writing a sapphic "Under the Tuscan Sun."

Jewish young adult literature has made leaps and bounds of progress in the last several years: Jewish YA on any subject used to be a rarity, but now, new releases that center Jewish protagonists are beginning to fill my shelves. A genre that used to be dominated by Holocaust literature has broadened and diversified to include not just books about our historical traumas but about romance, joy and all the messiness of life.

Haley Neil’s books are emblematic of that shift, and of the opportunities that now exist for writers and readers hungry for fresh and authentic depictions of contemporary Jewishness. Whether tackling an organized tour to Israel (as in ”Once More With Chutzpah”) or falling in love while on the asexuality spectrum (in a gorgeous Vermont apple orchard!), as she does in her new novel “Planning Perfect,” Neil’s Jewish heroines are intensely relatable — especially if, like me, you are a musical theater nerd with many opinions about the best challahs in the metro Boston area. I was so excited to chat with Haley around the release of “Planning Perfect” to talk writing while Jewish, vulnerability, “Gilmore Girls” and more.

This conversation has been edited and condensed for clarity.

To start, how would you describe “Planning Perfect”?

I’ve been calling it my “Gilmore Girls, but make it Jewish” book. It is a YA rom-com about Felicity Becker, who is 16 and finds out that her mom is getting married and hears that and thinks, “Wow! I will plan the entire thing! I am in charge now!” In the process of planning this wedding, she convinces her mother and her mother’s fiancé that they should do it at a Vermont apple orchard where, what a coincidence, her long-distance friend just happens to live. Just a friend and definitely nothing more than a friend, her gal pal, if you will…

Ha, love it! I could definitely see the “Gilmore Girl” vibes when I read, which I appreciated as someone who was always a bit frustrated with Gilmore Girls being very Jewish-coded while ultimately not being Jewish. 

It’s funny that you bring up “Gilmore Girls” being sort of Jewish-coded, but then also so WASP-y. When I was revisiting the show, in the very last episode, almost at the very end of the entire show, Lorelai makes a joke about her wedding and says, “Then we step on the glass!” And Luke says something along the lines of, ”We’re not Jewish.” Lorelai goes, “We’re not Jewish?” and I had a moment where I was like, “Exactly, exactly!”

What made you decide to write this story?

There’s two answers to this. The first, silly answer is that I made a joke. This happens sometimes. In this particular case, I made a joke that I was going to write a sapphic version of “Under the Tuscan Sun.” I made a joke because I was watching the movie and felt that it should have been a queer story. It happens a lot, watching something and thinking, “Oh, that’s a missed opportunity!”

The other reason was that I wanted to tell an ace-spectrum story that wasn’t about figuring out your identity. It was that next step of, well, what does it look like in practice?

Did you know from the start that you wanted this to be a Jewish story?

From the very beginning, I knew that Felicity was a Jewish character. I’m not sure when I realized I wanted to explore the differences of attitudes toward Jewish observance within the family, but as I started to see this very untraditional mother figure, I enjoyed exploring the dynamics between the three generations of women in this family and how intergenerational trauma plays into all that. I also loved showing untraditional traditions and the women connecting in different ways to their culture, whether it’s the details of the wedding or the challah — which is hopefully from the good kosher market, even if it’s a little bit out of the way. But that doesn’t mean there aren’t heavier moments in it connected to Jewishness. I’m a firm believer in bridging the heavier moments and the lighter moments to tell a full story.

Are there similarities in the way Felicity thinks about her queer identity and her Jewish identity? Are there differences?

Yeah! One thing that I loved for Felicity is that she’s not questioning necessarily what her identity is, as she already knows it. She knows that she’s Jewish, and it is how she explains her family background when people ask where she’s from; she says that it’s hard to pin down exactly where they’re from because of the way the diaspora works, but she can say she’s Jewish. She also knows that she falls underneath the asexual umbrella. That’s not the question. It’s that next step of figuring out what an identity means in practice. “OK, I know who I am, what am I going to do about it? How is it going to apply in my life?”

Are there similarities between how Felicity thinks of her identity and how you think of your own?

As someone who is also on the asexual spectrum, I do struggle with those feelings of “am I enough?” in queer spaces. And I have struggled with those feelings of “am I enough?” in Jewish spaces.

On the one hand, there’s that part of my brain that knows everyone connects to their personal backgrounds in different ways — and that ultimately, it’s your personal background. But then there’s always that other voice that says, “Are you enough? Do you fit? Are you in the right spaces?” It’s hard to talk about, but as an author, there is an expectation that we’re supposed to be vulnerable and upfront about all parts of our background, and then there are also a lot of assumptions that get made — particularly about asexual identity, but with Jewish identity as well.

Is that something you struggle with?

I think a lot about authors like Becky Albertalli, who has seen so much scrutiny about her own identity. Authors see the way that other authors are being treated and the way that assumptions around their identities are explored and exploited in such a public space, and it is intimidating.

It’s wild to think about writing in this way, because on the one hand writing is this quiet act of sitting at your computer or your notebook. It’s you and the words. But then those words go out to other people. You watch how people connect in different ways. I have actually had so many utterly heartwarming moments. There have been a lot of Jewish readers who’ve reached out and talked about how meaningful it is to see to see that representation. I had a couple of experiences where readers have reached out and talked about how seeing asexual spectrum identities in stories has helped them think about their own feelings and think about themselves. You never assume that your writing is going to reach people in that way.

Is there advice you have for Jewish writers?

I’m going to preface this by telling a bit of a story. I got my MFA at The New School, specifically in writing for children and young adults, and as a part of the program, we had a critical thesis where you could interview authors. I decided to do a piece where I interviewed Jewish authors who wrote Jewish stories. This was some time ago, and a theme that really fascinated me was that many authors had initially written characters who weren’t Jewish, and they were inclined to do so because they thought that if they wrote a Jewish story, no one’s would publish it.

For those writers to then actually write Jewish stories was a risk. And I am so grateful that they did that — because now you see lists, on bookstagram and elsewhere, of awesome upcoming Jewish romances and YA books, and there are options! And that is amazing. But that wouldn’t have happened without that initial choice those writers made, to write something that is more closely aligned with their background, versus what at the time was being published. It was huge.

So I would say: Take that risk to tell a truthful story, to tell your story.

My other piece of advice is to find community. First, because there are so many moments when having input and advice can be helpful, from technical elements to input from different voices of different backgrounds. That can be so deeply helpful in working on your story. And then specifically as a Jewish author, I am honored by the people in the book community who are doing so much amazing work. Looking at Jewish bookstagram, I am in awe of these creators who are spreading the word about these amazing books.

How was the process of writing this book? How was it different from your previous book?

So different. I was working with my wonderful publishing team at such an earlier stage. It went through major changes — I think so much of writing is revising. I completely reworked the relationship timeline because I found that I was writing to the beats of the types of rom-coms I had read before, and that did not make sense for an asexual spectrum character. It was following a pattern and a formula that didn’t fit for these two characters. And I completely reworked that in revisions to try and tell a more honest story.

What would you recommend to someone who has just finished “Planning Perfect”?

Loveless” by Alice Oseman and “The Lucky List” by Rachael Lippincott are two I’d recommend, as well as “The Sound of Stars” by Alechia Dow.

Then there are just so many amazing Jewish folks! I feel like I can’t narrow it down. I already mentioned Becky Albertalli; I will read whatever she writes. I will also read whatever Rachel Lynn Solomon writes. She could write a grocery list, and I would like to read it. Marissa Kanter’s writing is brilliant, and Dahlia Adler. The list goes on and on, there’s so many authors. And that’s amazing.

Definitely, and ten years ago, you wouldn’t be able to say the same thing about YA.

Oh, I remember looking for Jewish books as a child and as a young adult, and only finding Holocaust books. It was hard to see this part of my identity boiled down to trauma. I have family that was murdered in the Holocaust — that’s certainly not a unique story for Jewish people. To have that background and, frankly, to see your own generational trauma displayed as entertainment for others is hard.

So when I talk about the books that are out now, I am overwhelmed by it. I am so happy that people can go into a bookstore or a library and see this variety of stories — good stories that show Jewish joy and Jewish characters doing all kinds of things, falling in love and making mistakes and learning and connecting to their identities in such varied ways. Because there’s not a single Jewish experience. I love that. Keep going.

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