What to Read Next, Based on Your Favorite 90s/00s Rom-Com
I ❤️ love stories.
Is there anything more enjoyable than a well-written rom-com? I feel like we don’t get enough new, good rom-coms anymore, except in book form. Maybe now that there’s a mad dash to adapt every Emily Henry novel, we can usher in a second wave of great movie rom-coms.
Anyways, I was reflecting the other day on how much my favorite rom-com films from my early years have shaped my reading tastes and interests as I dive more into the romance genre. So I decided to put together some book recs based on some of my personal favorite movies from the 90s and 2000s.
When Harry Met Sally (1989)
Okay this one came out in the eighties, technically, but CLOSE ENOUGH. I think this is my favorite movie. I just love it. I quoted it on my wedding invitations (“When you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible.” because we decided, mid-COVID, to scrap our ceremony plans and get married with two weeks notice).
Anywho. Books!
You, Again by Kate Goldbeck
Ari is free-spirited, go with the flow, and anti-commitment. Josh is driven, ambitious, and has a rigid set of rules and expectations for his live. The two have nothing in common – except that they’re sleeping with the same woman. They never expect to cross paths again, but years later they’re both reeling from breakups and bump into each other – and an unlikely friendship blossoms. Soon enough they’re best friends, until the lines of their platonic relationship start to blur…
Literally billed as a retelling of When Harry Met Sally, Exit Lane follows Teddy and Marin, two polar opposites who have had more than enough of each other by the time they get from Iowa City to NYC after college. But their paths keep crossing over the course of eight years, bringing them together as friends, and maybe something more…
We Met Like This by Kasie West
Margo is a certified hopeless romantic who keeps encountering the same guy, Oliver, on every dating app. They went on one disastrous first date and called it quits, but she can’t seem to escape him. She meets Oliver in person again after being fired from her dream job, and he thinks she’s only in it for the physical side of things… Granted, they have very little in common, but Margo just can’t shake him. As she embarks on a new journey of starting her own literary agency, Oliver is there every step of the way as a cheerleader and helping hand… and eventually, something even better.
13 Going on 30 (2004)
You know, growing up, I never gave this movie too much thought. I watched it and enjoyed it, sure, but I feel like it’s only in hindsight (ironic!) that I realize how much I adore this film.
The MASH Up by Laura Marie Meyers
Okay, this doesn’t come out until July but I had to include it because it’s so perfect! A woman makes a wish on her 35th birthday and wakes up to find herself living inside one of her MASH games from seventh grade. Her intended other half is her brother’s annoying(ly handsome) best friend – and she realizes she has to make him fall in love with her if there’s any hope of completing the MASH game and getting back to her real life.
This Time Tomorrow by Emma Straub
On the morning of her 40th birthday, Alice wakes up back in 1996, reliving her 16th birthday all over again. While it’s all quite shocking, the biggest difference is seeing her dad fully healthy and as she remembers him, not the ailing, elderly man he is now. Armed with a new perspective on her life and relationships, Alice has the chance to change her future. This one is definitely more focused on familial relationships than romantic ones, but has all the heart and introspection of 13 Going on 30.
The Do-Over by Suzanne Park
While this one doesn’t involve actual time travel, it centers around Lily, who finds out during a job hunt that she actually didn’t earn enough credits to graduate (nightmare fuel). She commits to fully going back to college – living on-campus, attending frat parties, eating in the dining hall, and reconnecting with her former-boyfriend-turned-TA. Along the way, she realizes she may have the opportunity to make different choices this time and has to decide if her high-powered corporate career actually makes her happy.
You’ve Got Mail (1998)
Another perennial classic. I cry every time she says “I wanted it to be you.” That said, in real life, I do think I would have a hard time forgiving someone who ran my beloved second-generation bookstore into the ground. Alas. I’m sure Amazon came along a few years later and destroyed Fox Books so, I guess they’re even now?
Battle of the Bookstores by Ali Brady
Josie and Ryan both manage bookstores on the same street. Josie’s is a serious literary enterprise, while Ryan’s store only sells romance novels. But when a new owner purchases both stores and decides to combine them, they’re thrust into competition – only one manager can remain. It’s a stressful time and the two butt heads constantly. Their only solace are the anonymous online pen pals they’ve made in a book forum. Little do they know, they’re actually chatting with each other…
The Neighbor Favor by Kristina Forest
Lily longs to be a children’s book editor, but she’s stuck in a dead-end job, feeling left behind in her career, relationships, and her family. Her only solace is an online correspondence with her favorite author – until he ghosts her. Months later, she’s still heartbroken but determined to move on. She needs a date for her sister’s wedding, and enlists her neighbor Nick for help. Little does she know, Nick is actually that same author, writing under a pen name. As the two get closer, Nick realizes that the Lily he’d fallen in love with via email is his shy, reserved neighbor. He agrees to set her up with a friend, but he can’t get her out of his head.
Book Lovers by Emily Henry
While this doesn’t have the exact plot of You’ve Got Mail, it involves two rivals in the publishing industry who find out they have more in common than they thought. Nora is on a begrudging trip to a tiny small town straight out of one of her client’s romance novels when she runs into Charlie, a big shot editor who she’s clashed with back home in NYC. Turns out he’s a local, and the two of them begin a tentative alliance when Charlie gets called in to edit Nora’s star author’s new book.
Sweet Home Alabama (2002)
I’m sure this movie didn’t age super well, given its subject matter (and also, as much as I love it, I would choose Patrick Dempsey every time. Dr. McDreamy was one of my very first celebrity crushes). But I love it, and for the longest time, I would stop to watch it every time I saw it on TV, which was OFTEN. Seriously, were the networks getting a kickback or something? Anyways, if you’re not familiar, it’s the classic “successful, high-powered business woman from the city has to come back to her backwater hometown” story, in this case because she’s engaged and needs to seek an actual divorce from her childhood sweetheart she was married to years before.
That’s pretty specific, so I picked books that felt spiritually the same – second-chance romances with childhood or high school loves. One of my all-time favorite tropes.
Every Summer After by Carley Fortune
This is probably the closest match – Persephone has left her quiet hometown of Barry’s Bay behind for a stylish apartment in the city, drinks with friends, and never getting too close to anyone. Until she receives a call that sends her back home – and back into the life of Sam, her former best friend. The pair spent six inseparable summers together before their budding romance imploded. Now that Percy is back home for Sam’s mother’s funeral, she’s forced to confront the choices they both made way back when – and her very real current-day feelings for Sam.
Slow Dance by Rainbow Rowell
Shiloh and Cary were inseparable in high school; everyone thought they would end up together. The pair spent their time dreaming about the day they could get out of their hometown – Shiloh was going to be an actress and Cary wanted to join the Navy. Now Shiloh’s thirty-three, and it’s been fourteen years since she talked to Cary. A divorced mom of two, back living in the house she grew up in, Shiloh’s life is nothing like she planned. When she’s invited to an old friend’s wedding, all Shiloh can think about is whether Cary will be there. Would Cary even want to talk to her, after everything?
Same Time Next Summer by Annabel Monaghan
Sam has a great job in Manhattan (unless they fire her), a perfect doctor fiancé (who gets on her nerves more often than not), and she’s in Long Island to tour wedding venues near her family’s beach house. The last person she expects to run into is Wyatt, her first love and the boy who broke her heart nearly fifteen years ago. The more time she spends around him, the more she remembers the person she used to be, and starts to wonder if her “perfect” life is really even what she wants.
The Proposal (2009)
High-powered hotshot editor Margaret faces deportation, but convinces her assistant Andrew to legally marry her for the green card. When she’s forced to accompany him to his hometown to meet his family, she’s finally able to let loose and learn a thing or two about herself – and Andrew.
An Academic Affair by Jodi McAlister
Sadie and Jonah have been academic rivals since they first crossed paths as undergrads thirteen years ago. Now that a highly coveted teaching opportunity has come up, their rivalry hits epic proportions. When Sadie notices that the job offers partner hire, however, she hatches a plot to get them both the job. All they must do is get legally married. It’s a simple win-win solution but when sparks begin to fly, it becomes clear that despite their education, these two may not have thought this whole thing through.
The Paradise Problem by Christina Lauren
Anna and Liam got married in college to access subsidized family housing on campus. The signed divorce papers after graduation (so she thought) and went their separate ways. Three years later, Anna is a starving artist and Liam is a Stanford professor. He’s one of the four heirs to the Weston Foods conglomerate, but has zero interest in working for the family business. He is interested in his nine figure inheritance, but there’s one catch. Due to a clause in his grandfather’s will, Liam won’t get a penny until he’s been married for five years. Just when he thinks he’s home free, Liam’s family demands to meet his mystery wife, and he’s forced to introduce his foul-mouthed, paint-splattered, not-so-ex wife, Anna.
And Then There Was You by Sophie Cousens
Stuck in an entry-level job and still living at home after a bad breakup, 31-year-old Chloe isn’t where she wants to be in life. The last thing she wants to do is to face the people who voted her “most likely to succeed” at her college reunion. She definitely doesn’t want to see her former best friend, Sean, who is now a hotshot director living Chloe’s dream life. Desperate to save face, she turns to a dating service. Rob, her handsome, well-read, charming match seems like the perfect plus-one. As Chloe reconnects with old friends, she begins to question everything she thought she wanted. Maybe revisiting the past is exactly what she needs to move forward…
Notting Hill (1999)
Good old celebrity x regular person (citizen? pedestrian? we gotta figure out a better word here). I’m always like “damn, Julia Roberts is kind of awful to Hugh Grant, why does he still accept her?” and then I think about how Julia Roberts may just be the most beautiful woman on the planet and I get it.
Set Piece by Lana Schwartz
Jack is a breakout actor still coming to grips with his newfound stardom. CJ is a bartender with big dreams about working in the film industry. The pair share a hot and heavy night together, and go their separate ways. Five years later, Jack shows up to set for his latest blockbuster, only to find CJ is the film’s production designer. But neither of them is the same person they were five years ago – CJ is a single mom, and Jack is a bona fide celebrity. Their chemistry hasn’t dimmed a bit, but is there room in their lives for anything more?
When in Rome by Sarah Adams
Amelia, known as Rae Rose to her fans, is burned out after years of maintaining her “princess of pop” image. Inspired by “Roman Holiday” she drives off in the middle of the night to Rome (Kentucky, of course). When Noah finds Amelia on his lawn in her broken-down car, he makes it clear he’s not up for any celebrity drama. Despite his better judgment, he lets her stay in his guest room until her car is fixed. But soon he starts to see a different side of Amelia. She’s kind, goofy, and lonely from years of public scrutiny. He can’t help but get closer to her, despite the fact that soon she’ll be leaving back for her glamorous life on tour. But Amelia’s starting to think it’s time to settle down, and Rome seems like the perfect spot.
Funny You Should Ask by Elissa Sussman
Chani Horowitz is a twenty-something writer looking for her big break. When she’s hired to write a profile of movie star Gabe Parker – her ultimate celebrity crush – she thinks she’s finally found it. What comes next proves to be life-changing in ways Chani never saw coming. A decade later, Chani, now a successful writer, is still getting asked about her profile of Gabe Parker. So when his PR team requests that they reunite for a second interview, she wants to say no. But those seventy-two hours are still etched in her memory. So… she says yes.
The Lake House (2006)
I swear I’m the only one who remembers/loves this movie because I never see it on any “best of” lists but I was obsessed with it when I was 12. Sandra Bullock, Keanu Reeves, they exist in the same house several years apart and can only communicate through a magic mailbox??? SIGN ME UP. Also as I’m typing this I’m thinking, maybe this isn’t a rom-com so much as just a romance but… whatever.
The Seven Year Slip by Ashley Poston
Something tells me Ashley Poston also remembers The Lake House, because this book has a very similar premise. When Clementine finds a strange man standing in the kitchen of her late aunt’s apartment, it seems like a soul connection – except he’s living seven years in the past. Her aunt always said the apartment was a wrinkle in time, and now Clementine has to figure out a way to make this relationship work while dealing with the time difference.
Over and Over by Becky Hunter
Lissa is at a low point in her life when she meets Ash, who seems familiar… then the flashbacks start. She realizes she’s met Ash in several past lives, in different bodies and situations, but she always falls in love with him. And every time, it ends badly. Lissa knows she eneds to do something different this time to get the happy ever after she and Ash deserve. But how is she supposed to do that when she’s not sure what went wrong before?
One Last Stop by Casey McQuiston
August is a cynical recent transplant to NYC. She’s expecting the city to affirm her worldview – that love and magic aren’t real, and that she’s better off alone. But then she meets a gorgeous woman named Jane on the subway and that all goes out the window. There’s only one problem – Jane is somehow, inexplicably, displaced in time from the 1970s. Now August has to use everything she tried to leave behind if she wants to help Jane, and maybe get her happy ending.
Clueless (1995)
Oh, Clueless, how I love you. Is it a LITTLE weird she ends up with her stepbrother? Yeah, I guess, but look, he’s not even her CURRENT stepbrother. And it’s young Paul Rudd. I get it, okay.
Emma, Jane Austen
I mean, I can’t not include the book that movie is literally based on. I admit I have not actually read this one yet, but it’s a classic for a reason. Beautiful, spoilt, vain and irrepressibly witty, Emma organizes the lives of the inhabitants of her sleepy little village and plays matchmaker with devastating effect.
Emma of 83rd Street by Audrey Bellezza and Emily Harding
Beautiful, clever, and rich, Emma has lived her entire life in her Upper East Side neighborhood with very little to distress her… until her budding matchmaking hobby results in her sister’s marriage. Now her sister’s gone, and Emma’s dealing with an entirely new emotion: boredom. So when she meets Nadine, a wide-eyed Ohio transplant, Emma not only sees a potential new friend but a new project. If only her overbearing childhood friend George would get out of her way.
Kamila Knows Best by Farah Heron
Kamila lives a life of comfort, filled with elaborate parties, a dog with more Instagram followers than most celebrities, a job she loves, and an endless array of friends who clearly need her help finding love. In fact, Kamila is so busy with her friends’ love lives, she’s hardly given any thought to her own… Fortunately, Kamila has Rohan, her handsome, successful family friend. Only lately, Kamila’s “harmless flirting” with Rohan is making her insides do a little dance. But when Kamila’s secret nemesis returns to town with an eye for Rohan, it seems like Kamila’s perfectly ordered life is beginning to unravel.
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Love this but I need 10 things I hate about you book recs tho!
Truly obsessed and now dying for Mash Up to come out! Amazing!