Best movies like 16 to Life

A unique, carefully handpicked, selection of the best movies like 16 to Life Starring Hallee Hirsh, Theresa Russell, Shiloh Fernandez, Will Rothhaar, and more. If you liked 16 to Life then you may also like: Sixteen Candles, Normal Adolescent Behavior, On the Line, Book of Love, The Breakfast Club and many more popular movies featured on this list. You can further filter the list even more or get a random selection from the list of similar movies, to make your selection even easier.

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Romantic comedy. A small town teenager's angst about sexual inexperience drives a comic quest for love and understanding on a birthday to end all birthdays.

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Sixteen Candles

A teenage girl deals with her parents forgetting her birthday and a crush on her high school's heartthrob.

Normal Adolescent Behavior

High school student Wendy has an odd relationship with her five friends: They're openly sexual with each other, swapping partners every week. But this is all thrown into turmoil when she meets Sean, a new student in school who has a crush on her. Wendy wants to be with Sean, but doesn't want to disappoint her friends, whom she has known since grade school. When she does decide to leave them, her best friend, Billie, threatens revenge.

On the Line

A young man (Bass) is smitten with a girl (Emmanuelle Chriqui) he meets on a subway train and spends the rest of the movie trying to reunite with her. The man's best friend (Fatone) helps him in his quest by wallpapering Chicago with posters and signs that soon become the talk of the town.

Book of Love

John Twiller takes down his high school yearbook and begins to reminiscence about that time he first moved into the neighborhood in 1956. His teenage self, Jack is obsessed with Lily one of the more popular girls around. The sole obstacle is Angelo, her bullying boyfriend. With the help of his pals Crutch, Floyd, and Spider, he makes every attempt possible to change her mind.

The Breakfast Club

Five high school students from different walks of life endure a Saturday detention under a power-hungry principal. The disparate group includes rebel John, princess Claire, outcast Allison, brainy Brian and Andrew, the jock. Each has a chance to tell his or her story, making the others see them a little differently -- and when the day ends, they question whether school will ever be the same.

Cake

A travel writer improves her love life when she becomes an editor for her father's wedding magazine.

Clueless

Shallow, rich and socially successful Cher is at the top of her Beverly Hills high school's pecking scale. Seeing herself as a matchmaker, Cher first coaxes two teachers into dating each other. Emboldened by her success, she decides to give hopelessly klutzy new student Tai a makeover. When Tai becomes more popular than she is, Cher realizes that her disapproving ex-stepbrother was right about how misguided she was -- and falls for him.

Pretty in Pink

Andie is an outcast, hanging out either with her older boss, who owns the record store where she works, or her quirky high school classmate Duckie, who has a crush on her. When one of the rich and popular kids at school, Blane, asks Andie out, it seems too good to be true. As Andie starts falling for Blane, she begins to realize that dating someone from a different social sphere is not easy.

Hiding Out

A very successful stock broker is called to court to testify against a mob boss who was into some inside trading. Andrew Morenski must become Max Hauser and go back to high school for protection from the mob.

The Sisterhood of the Traveling Pants 2

Four young women continue the journey toward adulthood that began with "The Sisterhood of the Traveling Pants." Now three years later, these lifelong friends embark on separate paths for their first year of college and the summer beyond, but remain in touch by sharing their experiences with each other.

6.8 / 10 2015 Romance Comedy
suggested by: user103q676d6a7

The DUFF

Bianca's universe turns upside down when she learns that her high school refers to her as a ‘DUFF' (Designated Ugly Fat Friend). Hoping to erase that label, she enlists the help of a charming jock and her favorite teacher. Together they'll face the school's mean girl and remind everyone that we are all someone's DUFF… and that's totally fine.

The First Time

Dave, a high school senior, spends most of his time pining away over a girl he can’t have. Aubrey, a junior with artistic aspirations, has a hot boyfriend who doesn’t quite understand her or seem to care. Although they go to different schools, Dave and Aubrey find themselves at the same party. When both head outside to get some air, they meet. A casual conversation sparks an instant connection, and, over the course of a weekend, things turn magical, romantic, complicated, and funny as Aubrey and Dave discover what it's like to fall in love for the first time.

Lucas

A socially inept fourteen year old experiences heartbreak for the first time when his two best friends -- Cappie, an older-brother figure, and Maggie, the new girl with whom he is in love -- fall for each other.

Happy Campers

Chaos and rampant hormones reign when teenage counselors are left in charge during their summer-camp director's absence.

Sex Appeal

Avery, a teenager with a tendency towards perfectionism, enlists her friend Larson to help her prepare for her first time with her long-distance boyfriend.

The Hottie & The Nottie

Nate moves to L.A. to track down Cristabel, the woman he's been in love with since childhood, only to discover that his plan to woo her only has one hurdle to overcome: what to do with June, Cristabel's ever-present, not-so-hot best friend? What's even more complicating is Nate's growing feelings for June, whose true beauty starts to emerge.

How to Deal

Halley is convinced true love doesn't exist based on the crazy relationships around her. Her mother is divorcing her father who is dating a younger woman Halley can't stand. Her crazed sister is planning a wedding but has second thoughts and her best friend has fallen madly in love for the first time leaving Halley to feel even more alone.

Lloyd

A boy learns that confidence and self-esteem are the greatest gifts.

My Life in Ruins

A Greek tour guide named Georgia attempts to recapture her kefi (Greek for mojo) by guiding a ragtag group of tourists around Greece and showing them the beauty of her native land. Along the way, she manages to open their eyes to the wonders of an exotic foreign land while beginning to see the world through a new set of eyes in the process.

Tru Loved

Recently relocated from San Francisco to conservative suburbia by her lesbian mothers, Tru struggles like all teens to fit in and find love, but her quest is complicated by sexual politics, closed minds, and closeted friends as she seeks to establish her school's first Gay-Straight Alliance.

The Perfect Date

No beau? No problem! To earn money for college, a high schooler creates a dating app that lets him act as a stand-in boyfriend.

Blue Citrus Hearts

A first love could quite possibly be the last for Sam, a Memphis teenager coming to terms with the romantic feelings he harbors for his best friend, Julian. Will the love he feels for this boy guide him through his struggles with his abusive father, ignorant girlfriend, and suicidal thoughts -- or will the conflict that his love for Julian stirs throughout his life prove to be more than one boy can handle?

Pizza

A pizza deliveryman develops a bond with a girl nearly half his age.

Old Boys

In the school-set re-working of Cyrano, an awkward but imaginative pupil helps the handsome but spectacularly dim school-hero pursue the fiery daughter of a visiting French teacher.

A Christmas Kiss

Wendy Walton is the best designer in Boston... but no one knows it yet. Hoping to kick-start her career, Wendy has left work with the local theatre to take a job as an assistant to Priscilla Hall, the most prestigious designer in the city. Ms. Hall works Wendy around the clock, which is how Wendy finds herself trapped in an elevator late one night with an incredibly handsome stranger. Wendy and the mystery man share an impulsive, romantic, life changing kiss before the doors open and Wendy runs out, leaving him behind. The next day at work, Wendy answers the door to find the handsome gentleman standing in front of her.

Dating & New York

After an electric one-night stand, two New York millennials draw up a friends-with-benefits contract to avoid the pitfalls of their past relationships

Heterosexual Jill

A self-proclaimed "ex-lesbian," Jill hunts down her ex-girlfriend Jamie to prove to herself that she is no longer attracted to her. "Heterosexual Jill" is a satire about sexuality where nothing is as it seems.

A Christmas Kiss II

At a Christmastime event, Jenna shares an impromptu, unforgettable kiss with the dashing billionaire, Cooper Montgomery. Unaware of his intentions and fearful of getting hurt in another relationship, Jenna vows to resist his charms, but begins to realize his affection is real as the two spend more time together.

Lust for Love

Winning your childhood sweetheart can create more problems than it solves.

The Bad Mother's Handbook

Karen Cooper wants to domineer her family and believes she's its pillar. In fact she does everything wrong. Thus she messes up all their lives and futures, rather then help her loved-ones.

The Right One

Sara, a novelist struggling with writer's block, needs inspiration — and finds it when she serendipitously meets Godfrey, a down-on-his-luck oddball who constantly changes personas and alter egos in order to cope with his past and avoid reality. Just as Godfrey begins to open up to Sara, he discovers that she’s been using him as inspiration for her next novel, and he vanishes from her life. Did Sara just lose the man of her dreams, or will she be able to find him and make things right?

The Sweeter Side of Life

Pampered Manhattan housewife Desiree Harper has it all. That is until her husband unexpectedly dumps her for his acupuncturist. Faced with an airtight prenup, Desiree reluctantly lands a job making cupcakes at her father's bakery in Flemington, NJ. She soon discovers there's more to life than 5th Avenue and true love can be even sweeter in small town America.

Sex and the Teenage Mind

Bumbling high school geek Virgil Heitmeyer has yet to lose his virginity. A golden opportunity for finally getting deflowered arises after Virgil manages to get closer to the beautiful and popular Kellie Guthrie. Will Virgil's date with Kellie go smoothly? Or is Virgil going to blow his big chance to score with the girl of his dreams?

4.0 / 10 2013 Comedy Romance
suggested by: popcornlover

Dry Spell

Sasha tries to get her soon-to-be ex husband Kyle laid so she can move on with her sex life guilt-free.

Young Hearts

Two young neighbors embark on a first love relationship in which they struggle to remain kids amid the complexities of modern adolescence.

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