Book picks similar to
Flirting with Maybe by Wendy Higgins


young-adult
contemporary
romance
new-adult

The Best Laid Plans


Cameron Lund - 2020
    She wants to have that experience too (well, not exactly like that--but with someone she trusts and actually likes), so she's going to need to find the guy, and fast. Problem is, she's known all the boys in her small high school forever, and it's kinda hard to be into a guy when you watched him eat crayons in kindergarten. So she can't believe her luck when she meets a ridiculously hot new guy named Dean. Not only does he look like he's fallen out of a classic movie poster, but he drives a motorcycle, flirts with ease, and might actually be into her.But Dean's already in college, and Keely is convinced he'll drop her if he finds out how inexperienced she is. That's when she talks herself into a new plan: her lifelong best friend, Andrew, would never hurt or betray her, and he's clearly been with enough girls that he can show her the ropes before she goes all the way with Dean. Of course, the plan only works if Andrew and Keely stay friends--just friends--so things are about to get complicated.Cameron Lund's delightful debut is a hilarious and heartfelt story of first loves, first friends, and first times--and how making them your own is all that really matters.

A Totally Awkward Love Story


Tom Ellen - 2014
    The book, which Sullivan calls The Statistical Probability of Love at First Sight meets Bridesmaids, is a dual narrative novel by authors who dated when they were in high school, about a boy and girl who must navigate social misunderstandings, the plotting of well-meaning friends, and their own fears about being virgins forever. It's slated for summer 2016; Allison Hellegers of Rights People brokered the deal on behalf of Barry Cunningham and Elinor Bagenal at Chicken House in the U.K.

The Unexpected Everything


Morgan Matson - 2016
    When you are a politician’s daughter who’s pretty much raised yourself, you learn everything can be planned or spun, or both. Especially your future. Important internship? Check. Amazing friends? Check. Guys? Check (as long as we’re talking no more than three weeks).But that was before the scandal. Before having to be in the same house with her dad. Before walking an insane number of dogs. That was before Clark and those few months that might change her whole life. Because here’s the thing—if everything’s planned out, you can never find the unexpected. And where’s the fun in that?

Welcome, Caller, This Is Chloe


Shelley Coriell - 2012
    Chloe is forced to take on a meaningful project in order to pass, and so she joins her school’s struggling radio station, where the other students don’t find her too queenly. Ostracized by her former BFs and struggling with her beloved Grams’s mental deterioration, lonely Chloe ends up hosting a call-in show that gets the station much-needed publicity and, in the end, trouble. She also befriends radio techie and loner Duncan Moore, a quiet soul with a romantic heart. On and off the air, Chloe faces her loneliness and helps others find the fun and joy in everyday life. Readers will fall in love with Chloe as she falls in love with the radio station and the misfits who call it home.

The Geek's Guide to Unrequited Love


Sarvenaz Tash - 2016
    Archie and Veronica. Althena and Noth.…Graham and Roxy?Graham met his best friend, Roxy, when he moved into her neighborhood eight years ago and she asked him which Hogwarts house he’d be sorted into. Graham has been in love with her ever since.But now they’re sixteen, still neighbors, still best friends. And Graham and Roxy share more than ever—moving on from their Harry Potter obsession to a serious love of comic books.When Graham learns that the creator of their favorite comic, The Chronicles of Althena, is making a rare appearance at this year’s New York Comic Con, he knows he must score tickets. And the event inspires Graham to come up with the perfect plan to tell Roxy how he really feels about her. He’s got three days to woo his best friend at the coolest, kookiest con full of superheroes and supervillains. But no one at a comic book convention is who they appear to be…even Roxy. And Graham is starting to realize fictional love stories are way less complicated than real-life ones.

Sophie & Carter


Chelsea Fine - 2011
    Carter is overwhelmed by issues at home as he struggles to support his mother. Meanwhile, next door neighbor Sophie is left to care for her three younger siblings in place of their absent and troubled mother. All that holds these two best friends together is each other, and knowing that each night they'll sit together on Sophie's front porch swing and escape from reality, if just for awhile. But as their relationship reaches a turning point and high school graduation nears, will their friendship become something more?

One of the Guys


Lisa Aldin - 2015
    She'll take horror movies, monster hunts and burping contests over manicures. So Toni is horrified when she's sent to the Winston Academy for Girls, where she has to wear a skirt and learn to be a lady while the guys move on without her.Then Toni meets Emma Elizabeth, a girl at school with boy troubles, and she volunteers one of her friends as a pretend date. Word spreads of Toni’s connections with boys, and she discovers that her new wealthy female classmates will pay big money for fake dates. Looking for a way to connect her old best friends with her new life at school, Toni and Emma start up Toni Valentine’s Rent-A-Gent Service. But the business meets a scandal when Toni falls for one of her friends--the same guy who happens to be the most sought-after date. With everything she's built on the line, Toni has to decide if she wants to save the business and her old life, or let go of being one of the guys for a chance at love.

What I Didn't Say


Keary Taylor - 2012
    He's been in love with her for years and never had the guts to tell her. Now it's too late. Because after that night, Jake will never be able to talk again.When Jake returns to his small island home, population 5,000, he'll have to learn how to deal with being mute. He also finds that his family isn't limited to his six brothers and sisters, that sometimes an entire island is watching out for you. And when he gets the chance to spend more time with Samantha, she'll help him learn that not being able to talk isn’t the worst thing that could ever happen to you. Maybe, if she'll let him, Jake will finally tell her what he didn't say before, even if he can't actually say it.

Unbreak My Heart


Melissa C. Walker - 2012
    She fell for her best friend’s boyfriend and long story short: he’s excused, but Clem is vilified and she heads into summer with zero social life. Enter her parents’ plan to spend the summer on their sailboat. Normally the idea of being stuck on a tiny boat with her parents and little sister would make Clem break out in hives, but floating away sounds pretty good right now. Then she meets James at one of their first stops along the river. He and his dad are sailing for the summer and he’s just the distraction Clem needs. Can he break down Clem’s walls and heal her broken heart?Told in alternating chapters that chronicle the year that broke Clem’s heart and the summer that healed it, Unbreak My Heart is a wonderful dual love story that fans of Sarah Dessen, Deb Caletti, and Susane Colasanti will flock to.

Magnolia


Kristi Cook - 2014
    Neighbors since the Civil War, the families have shared vacations, holidays, backyard barbecues, and the overwhelming desire to unite their two clans by marriage. So when a baby boy and girl were born to the families at the same time, the perfect opportunity seemed to have finally arrived.Jemma Cafferty and Ryder Marsden have no intention of giving in to their parents’ wishes. They’re only seventeen, for goodness’ sake, not to mention that one little problem: They hate each other! Jemma can’t stand Ryder’s nauseating golden-boy persona, and Ryder would like nothing better than to pretend stubborn Jemma doesn’t exist.But when a violent storm ravages Magnolia Branch, it unearths Jemma’s and Ryder’s true feelings for each other as the two discover that the line between love and hate may be thin enough to risk crossing over.

Art Geeks and Prom Queens


Alyson Noel - 2005
    A New York transplant, Rio has no clue how she's going to fit in at her fancy new private school in Southern California. Plus, being late, overdressed, and named after a Duran Duran song doesn't make the first day any easier for her.Then Rio meets Kristi. Beautiful, rich, and a cheerleader, Kristi is the queen bee of Newport Beach. And Kristi isn't friends with just anyone, so Rio is thrilled when she's invited to be part of the most exclusive, popular clique. Of course, like any club, Kristi and her friends have rules: Always smile (even if you don't mean it), always dress cute (and never repeat outfits), and always flirt (but only with jocks, preps, and rich college guys). At first Rio is having a great time, but as she becomes more immersed in this jet-set crowd, she figures out there is one last rule that her new friends forgot to mention: Don't cross Kristi . . .

In Honor


Jessi Kirby - 2012
    Its contents are a complete shock: concert tickets to see Kyra Kelly, her favorite pop star and Finn’s celebrity crush. In his letter, he jokingly charged Honor with the task of telling Kyra Kelly that he was in love with her. Grief-stricken and determined to grant Finn’s last request, she rushes to leave immediately. But she only gets as far as the driveway before running into Rusty, Finn’s best friend since third grade and his polar opposite. She hasn’t seen him in ages, thanks to a falling out between the two guys, but Rusty is much the same as Honor remembers him: arrogant, stubborn . . . and ruggedly good-looking. Neither one is what the other would ever look for in a road trip partner, but the two of them set off together, on a voyage that makes sense only because it doesn’t. Along the way, they find small and sometimes surprising ways to ease their shared loss and honor Finn--but when shocking truths are revealed at the end of the road, will either of them be able to cope with the consequences?

Fan Art


Sarah Tregay - 2014
    Not college—that’s all set. Not prom—he’ll find a date somehow. No, it’s the worst problem of all: he’s fallen for his best friend.As much as Jamie tries to keep it under wraps, everyone seems to know where his affections lie, and the giggling girls in art class are determined to help Jamie get together with Mason. But Jamie isn’t sure if that’s what he wants—because as much as Jamie would like to come clean to Mason, what if the truth ruins everything? What if there are no more road trips, taco dinners, or movie nights? Does he dare risk a childhood friendship for romance?This book is about what happens when a picture reveals what we can’t say, when art is truer than life, and how falling in love is easy, except when it’s not. Fan Art explores the joys and pains of friendship, of pressing boundaries, and how facing our worst fears can sometimes lead us to what we want most.

A Little Something Different


Sandy Hall - 2014
    They get the same pop culture references, order the same Chinese food, and hang out in the same places. Unfortunately, Lea is reserved, Gabe has issues, and despite their initial mutual crush, it looks like they are never going to work things out.  But somehow even when nothing is going on, something is happening between them, and everyone can see it. Their creative writing teacher pushes them together. The baristas at Starbucks watch their relationship like a TV show. Their bus driver tells his wife about them. The waitress at the diner automatically seats them together. Even the squirrel who lives on the college green believes in their relationship. Surely Gabe and Lea will figure out that they are meant to be together....

The Boyfriend Thief


Shana Norris - 2011
    2 former BFFs. 11 days to seduce a boy. Avery James doesn’t believe in romance—she’s studied enough biology to know that love is nothing more than hormones and chemicals. Besides, she has more practical goals in mind, namely saving up for a summer humanitarian program in Costa Rica. But when her Diggity Dog House supervisor denies her a raise and Avery finds herself $500 dollars short for the trip of a lifetime, Avery has no choice but to accept an unexpected offer. The deal? She must steal her arch nemesis Hannah’s boyfriend before prom, giving Avery eleven days to seduce Zac Greeley. Avery is sure the job will be easy. But a few midnight comedy shows and spontaneous dance parties (not to mention one particularly intimate carwash) later, Avery finds herself questioning everything she’s ever thought about love. Could Zac’s signature cherry-lime Slurpees be causing brain freeze, or is Avery actually starting to fall for him? Will Avery be able to steal Zac away from Hannah before he steals Avery’s heart?