Romance/Erotica

10 Hilarious and Heartfelt Books like FUNNY STORY

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Isabelle Popp

Senior Contributor

Isabelle Popp has written all sorts of things, ranging from astrophysics research articles and math tests to crossword puzzles and poetry. These days she's writing romance. When she's not reading or writing, she's probably knitting or scouring used book stores for vintage gothic romance paperbacks. Originally from New York, she's as surprised as anyone that she lives in Bloomington, Indiana.

Books like Funny Story aren’t so easy to come across. In these trope-saturated rom-com days, matching the tropes one-to-one simply won’t suffice. What makes Emily Henry stand out in the crowd is that her writing doesn’t rely too much on the tropes. Emily Henry’s novels are full of fully realized characters with big flaws and plenty of baggage. Virtually all of her novels put a secondary storyline, usually a reckoning with family members or friends, on a nearly equal footing with the romance itself.

Don’t get me wrong, Funny Story is trope-tastic. It’s got two recently jilted opposites who, thanks to their forced proximity as unlikely roommates, hatch a goofy fake dating plot. Daphne is a little rigid and aloof. Miles is charming but rough around the edges — he’s got that Nick Miller from New Girl quality. He’s definitely not going to be everyone’s “book boyfriend,” but he brings out the best in Daphne, and vice versa. They figure out a lot about themselves through each other, and that’s the magic to witness.

That’s also the magic I’ve tried to capture in finding more books like Funny Story. They will share a trope or two, but the thoughtful character development is what’s really going to get you. While Emily Henry’s books may be a cut above in terms of sales and popularity, I promise she’s got some competitors in the storytelling.

Cover of Role Playing by Cathy Yardley

Role Playing by Cathy Yardley

If you like witnessing a friendship between opposites blossom into something more, here’s a great pick for you. Maggie’s the grump; Aiden’s the sunshine. They know each other through online gaming, but they have the totally wrong ideas about each other, age-wise. When they meet in person and find out who was on the other end of the line, everything changes. They both have complicated pasts that threaten their ability to make relationships work, like many an Emily Henry character, but they find a way.

cover of Lips Like Sugar

Lips Like Sugar by Jess K. Hardy

Caving to the impulse to bring a revenge date to a wedding ties this book to Funny Story. In Lips Like Sugar, Mira wants to bring the sexy stranger she just met to a wedding, and luckily, he agrees. Cole is a former rock star and is — no joke — the bisexual grandfather of your dreams. What started out as a lark turns into something real. Again, these characters are wonderfully nuanced with messy lives, and you will absolutely be rooting for them.

cover of Stars in Your Eyes by Kacen Callender

Stars in Your Eyes by Kacen Callender

I’m generally on the record as a fake dating hater (how is this a thing adults do?!?!), but I made an exception for Funny Story and Stars in Your Eyes. After all, Stars in Your Eyes is a Hollywood romance, the one place where fake dating seems to be a real thing. Hollywood bad boy Logan publicly disses his new costar, Mattie. A fake relationship should solve this PR crisis, right? Despite the fluffy premise, this book really digs into trauma and healing in a way I absolutely loved.

Book cover of Georgie, All Along by Kate Clayborn

Georgie, All Along by Kate Clayborn

If you’re looking for books like Funny Story, you simply need to be reading everything Kate Clayborn writes. Her books aren’t especially comedic, but they have plenty of fun and whimsy along with the heartfelt emotions. If you like opposites-attract stories about roommates, this is it. Georgie is a personal assistant who’s never figured out what she really wants. Levi, Georgie’s surprise roommate in her hometown, is a gruff guy with a bit of a bad reputation in town. This story follows them shedding all their layers to find their true selves together, and it’s lovely.

funny guy cover

Funny Guy by Emma Barry

What I love about Funny Guy is that, like in Funny Story, the male main character is also not going to be everyone’s cup of tea. Sam is dramatic, in a fun way. He’s a famous comedian whose ex just released a pop hit roasting him. He’s licking his wounds at his lifelong friend Bree’s apartment. She’s been pining for him forever and he doesn’t know. It’s got that tentative friends-to-lovers plot, it’s got yearning for days, and it’s got big emotions. As I write this I’m convincing myself it’s time for a reread.

The Comeback by Lily Chu Book Cover

The Comeback by Lily Chu

If you can relate to a woman who’s trying to do everything right and is hanging onto that “perfect” life by a thread, pick The Comeback up. Ariadne is such a woman, so you know it’s going to throw her for a loop when her roommate’s cousin, the chaotic and recently heartbroken Jihoon, is couch-surfing for a while. This book obviously is a very close match for Funny Story setup-wise, but it also has very loveable characters trying to figure out their futures.

If the Dress Fits by Carla Guzman book cover

If The Dress Fits by Carla de Guzman

More wedding fake dating! Martha is a fat woman who has a realistically complicated relationship with her body and other people’s opinions about it. When everyone is coming for the wedding of the guy she’s holding a torch for, a fake boyfriend ought to keep the heat off her. Enter her best friend Max, who fills the role perfectly. Maybe a little too perfectly? This book has tons of family drama, great food descriptions, and lots of proper rom-com beats.

cover image of Like Lovers Do by Tracey Livesay

Like Lovers Do by Tracey Livesay

If you like friends-to-lovers mixed with fake dating, here’s another book to add to the mix. And this one is sexy! Nic is a driven doctor who’s facing some discrimination that may affect her career. Oddly enough, her landlord Ben’s family might be able to help her keep her job. So, she agrees to accompany Ben as a fake girlfriend on a trip to Martha’s Vineyard. They’ve been friends for a while, but this trip shows them what else might be possible. This book has a hammock scene you will not want to miss.

house rules cover

House Rules by Ruby Lang

There is something so New York City about living with your ex because the apartment is too good a deal to pass up. That’s what brings Simon and Lana back together despite the fact that they’re literally DIVORCED. They’ve established strict boundaries and a time limit, but their time apart has given them the time to grow that they both needed. If you like Emily Henry’s books because the characters feel so real, you simply must get into Ruby Lang’s backlist.

cover of Count Your Lucky Stars

Count Your Lucky Stars by Alexandria Bellefleur

“…and they were roommates!” Your ears perk up, right? Margot and Olivia end up living together despite being exes. Not just exes, but first loves! Nowadays, Margot only keeps things casual, but Olivia’s reappearance in her life after ten years makes her question that stance. But things went so wrong the first time! You see the source of the angst. If you like dirty talk in your romances, you will LOVE Margot.


I’ve endeavored to give you books like Funny Story by Emily Henry that really balance rom-com tropes with rich character arcs. But maybe there’s a different ingredient in that Emily Henry magic sauce that you’re looking for. Or maybe you tear through this list and you’re hungry for more. Whatever the case, the dedicated bibliologists at Tailored Book Recommendations will help you find the perfect books that will satisfy your readerly appetite.