Hollywood has taught us that you're probably destined to be with your younger-self BFF. There are countless movies about it, across decades: 13 Going on 30, When Harry Met Sally, Some Kind of Wonderful, and even the Melissa Joan Heart masterpiece Drive Me Crazy. But it's not all Hollywood; though they are not quite as prominent as the movies, there are some great books about falling in love with childhood best friend.
Even as someone who did not marry her childhood best friend, I fully believe in the teenage and even grown-up desire to end up with someone who has known you when you forgot your lunch in kindergarten, or when you had your first heartbreak in middle school, or who tagged along in your crew for the prom in high school. However, sometimes friends are just friends for a reason, and these BFF-turned-lover relationships just don't work out.
In the seven books in this list of childhood sweetheart novels, there is a mix of happily ever after (at least within in what we know in the confines of these pages), unrequited crushing when one person falls desperately for his or her friend, and full-blown disaster. And, as it turns out, these issues range from middle grade books to young adult to even adult fiction, both classic and contemporary.
1. Shug by Jenny Han
If I were Shug's childhood BFF, I would totally fall in love with her. Annemarie "Shug" Wilcox is in the awkward, about-to-start-junior-high phase that we all shudder to remember, and as she starts to see the world and the people around her with slightly grown-up eyes, she develops an unstoppable crush on her BFF Mark. But as we all remember from those days, unrequited love is par for the course, and Mark doesn't feel the same way back. (Clearly Mark has poor taste because Shug is my favorite, and she's named in homage to The Color Purple so....)
2. Her Name In The Sky by Kelly Quindlen
Hannah's conservative Louisiana community's values have been impressed upon her since she was a child. So when she starts to fall for her female best friend Baker, she knows she should instead be crushing on Wally, who asked her to prom. But who can deny the kind of charge Hannah feels with Baker, when they're up late at night eating mac and cheese and talking endlessly? It's scary to fall for your best friend, and it's even scarier when your whole heart wants something your world says is wrong.
3. Emma by Jane Austen
Longtime friends Mr. Knightley and Emma Woodhouse eventually realize that they're the ones in love in Jane Austen's classic Emma. Throughout the novel, Mr. Knightley and Emma banter back and forth and argue over matchmaking and love interests, but when Emma is faced with watching her friend, Harriet, fall for Mr. Knightley, she knows that she is the one that loves him. (And when you put old-school Paul Rudd or Jonny Lee Miller in the role, it's not hard to see why.)
4. Never Let Me Go by Kazuo Ishiguro
I have to get through this one quickly before I start crying. Whew, here goes: There are not one but two sets of childhood best friends falling in love in this devastatingly beautiful Kazuo Ishiguro novel. First, there's Ruth and Tommy, boarding school student BFFs who grew up together and later start a romantic entanglement. After that, fellow best friend Kathy and Tommy fall for each other, as adults, and begin a relationship they literally believe will save their lives. And, um, excuse me while I go smother myself in tissues.
5. The Summer I Turned Pretty by Jenny Han
Jenny Han is clearly the queen of childhood best friends-turned wannabe lovers, as this is her second appearance on this list, and in The Summer I Turned Pretty series, Belly falls for two of her BFFs. Belly knows summer is the only time of year. It's when she goes to the cottage by the ocean with her mother and brother to meet up with her mother's best friend and her two sons, Conrad and Jeremiah. But as Belly is getting older, she finds a growing attraction, and even love, with both of the boys who have defined her summers as long as she can remember. Passion, romance, and major drama ahead. Oh, and #TeamConrad forever.
6. The Square Root of Summer by Harriet Reuter Hapgood
Gottie and Thomas were trouble-making childhood best friends, until Thomas' family moved him from England to Canada. But this summer, Thomas is returning to spend months with Gottie and her family. But it's odd timing for Gottie: Not only has her beloved grandfather recently died, but she's experiencing wormhole-like time lapses. Oh, and her first secret love Jason has a new girlfriend. But Thomas and Gottie slowly start to experience that magic that sparked their early friendship, and it may start to develop into something even more.
7. Love, Rosie by Cecelia Ahern
From the author who brought you ugly cries in the form of P.S. I Love You, is Love, Rosie (sometimes called Where the Rainbow Ends). Rosie and Alex have been best friends since they were little kids, and they've always waved off comments from all their friends about how they are destined to be with each other. But through the years, years of breakups and loves and life struggles, including a Rosie's child who is not Alex's, their bond only strengthens. And finally, finally, the timing may be right for their friendship love to grow into something more romantic.