Adi Alsaid speaks with me on his American cellphone; he has two, one he uses when visiting family in Las Vegas, where he attended school and one for Mexico, where he was born and raised by Israeli parents and now writes and teaches school in an artsy neighborhood he calls the “Greenwich Village of Mexico City.”

Alsaid’s ease with borders and boundaries makes him a natural author for Never Always Sometimes, which focuses on best friends who fall in—and out of—love, transgressing the boundaries of relationships.

Those best friends are Dave and Julia, high school seniors who drew up a Never List of clichés to avoid, ranging from No. 1: Never be recognized by your lunch spot. Keep moving, to No. 10: Never date your best friend.

In the last few months of high school, impulsive daredevil Julia suggests they cross every Never off the list, using clichés to explore an even wilder side of their friendship. Yes, even No. 5: Never dye your hair a color found in a rainbow.

Darkly comic, the book explores the tensions between being yourself and fitting in, the borders of where you end and others begin. “When you’re a teenager, you’re constantly trying to figure out who you are, how you fit into the world around you,” Alsaid says. “You want to stay unique and original but also get along with everyone.”

And all along, Dave has been violating No. 8: Never pine silently after someone for the entirety of high school. Julia and Dave head down a path unforgiving of both U-turns and happy endings. At its heart, the novel reveals that what you want isn’t always what you need, and even the mature, platonic love of true friendship exacts a price.

Jacaranda trees and sunny beaches easily place the novel along the California coastline, where Alsaid lived after college, working on his first novel, Let’s Get Lost. Alsaid started writing in middle school and high school, mostly unfinished short stories and small bits for the school newspaper. Three days from college graduation, he panicked—employers were turning down his applications.

His backup plan? Move to California, become a writer. He gave the plan three years to succeed. “I went and wrote a couple books without anything happening, “ he says. “Then three years to the day of my decision, I signed two-book deal with Harlequin teen. “

Writing a second novel wasn’t quite as arduous as the first, he says, which saw 17 rewrites. This book only took four or five iterations. The quick timeline was necessary, as he had a mere six weeks for his first draft. “I was doing rewrites all summer,” he says.

The comic, conversational tone of the books’ teens comes naturally to Alsaid, no slouch in the language department. The trilingual author speaks English, Spanish, and Hebrew.

“I did want to write a funnier book,” he says. The duo’s smartass repartee is one of the book’s more delightfully surprising aspects. “The two characters naturally came about, and it flowed easily. Sometimes it’s hard to write comedy, you can’t tell people, ‘This is funny.’ But when I started getting notes back from my editor with a little LOL, I knew it was working.”

Alsaid doesn’t shy away from controversial—albeit honest—teen topics in Never Always Sometimes. The book’s drinking party involves bad behavior and Julia’s disappointed dads. “I wanted to tackle putting Dave and Julia into all these clichés,” he says, pointing out the revered parents-are-out-of-town-let’s-drink trope in every teen movie, ever. “I wanted to put them in that situation, and maybe then put real-life spin on it.”

For his upcoming book tour, Alsaid is excited to reengage with supportive and friendly reading and writing community—the YA authors, the librarians and booksellers. After that, he’ll return to Mexico City.

But first, he’s going to Asia on a two-week trip, ready to cross more boundaries.

Lora Shinn is a former youth and teen services librarian and now writes full-time about literacy, health, and travel.