Danielle Sepulveres
February 06, 2015 10:58 am

With Valentine’s Day fast approaching, I’ve got romance on the brain. More specifically? The dynamic of a first kiss. There’s a lot riding on a first kiss! And not just your first kiss ever (I was thirteen and expecting a life-altering moment and ended up kinda grossed out by the whole thing). Every time you start a new relationship, the anticipation of the first kiss weighs heavily on our minds. Will it be good? Awkward? Romantic? Sexy? Will we have crazy chemistry and kiss for hours? Will we hate it and never want to call this person again?

SO MUCH PRESSURE.

Some of this anxiety is due in part to wonderful movies that give us our starry eyed notions of the perfect first kiss. Who doesn’t want to be made to feel like they’re flying on the bow of a ship (even a doomed one) while Leonardo DiCaprio holds you and then kisses you with the reckless abandon that only a passenger from steerage can? *raises hand*

There are all kinds of first kisses, but sometimes the ones that speak to me the most are the sweet, somewhat awkward ones. They feel more real, and perfectly capture that moment of being unsure and not knowing where it might possibly lead. Here are some of the sweetest first kisses to grace the movie screen. Spoiler alert: Be prepared to say “awwww” several times.

Sixteen Candles

Molly Ringwald—one of the original teen angst heroines! As the smart, quiet Samantha, she spends the entire movie trying to get up the nerve to talk to Jake, the school hottie. Unbeknownst to her, he is trying to do the same. The film ends with them sitting on a table, a birthday cake between them as he tells her to make a wish and she says, “It already came true.” Cue the super sweet kiss over the cake!

Never Been Kissed

Drew Barrymore as Josie Geller gets a do-over at high school as an undercover reporter—a fantasy many of us wouldn’t mind indulging sometimes. She not only stands up to the school mean girls, but she also falls in love with a guy who gives her a meaningful and genuine confidence boost, and later her first real kiss that she’s been waiting for her whole life. It’s all the more sweet because it happens on a baseball field in front of a cheering crowd of people rooting for her to finally have her romantic moment. Because everybody loves love!

Titanic

Pretty self explanatory, as mentioned above. Leo and Kate. Jack and Rose. A kiss that starts as sweetly hesitant and quickly becomes super passionate. Sigh. Thanks for setting the bar so high, you two.

The Princess Bride

This movie is synonymous with sweet romance; and all the more so because of the narration. While Westley and Buttercup are about to share an incredibly romantic first kiss, it cuts back to Peter Falk and Fred Savage, with Savage getting grossed out that his grandfather would deign to read him a “kissing book.” It contributes to the overall innocence and sweetness to the love story.

Good Will Hunting

Besides being sweet, this might be one of the coolest and most fun first kisses of all time. Matt Damon and Minnie Driver opt not to wait until the end of the night of their first date, and just go for it right in the middle (in between bites of food, no less!). I’ve been on many a date where I’ve nervously wondered about the end of the evening kiss, and this movie totally kicks that cliché to the curb in such an unexpected but really adorable way.

One Fine Day

Over the course of one day, Michelle Pfeiffer and George Clooney—who are both divorced, single parents—meet for the first time and completely fall for each other. They’ve both been hurt, and as a result have fostered their own daily routines that don’t allow much room for another person to be a real romantic possibility. A fact that eventually culminates in a totally “awwww”-inducing honest conversation about it and an amazing first kiss at the very end of the day.

Blue is the Warmest Color

Everything about this kiss was so sweet and lovely and perfect. The way Adele and Lea look at each other, and the way they sort of laugh at the awkwardness of it all—it perfectly captures what it’s like to be young and in love and a little unsure but ultimately unable to help yourself. Could this kiss be any sweeter?!

10 Things I Hate About You

Heath Ledger serenades Julia Stiles in front of their high school. She flashes a teacher to get him out of detention for it. They ride on a paddle boat and then go play paintball. How else would this incredible day end if not with the sweetest kiss in a pile of hay on the paintball obstacle course?? And why weren’t dates (and kisses) like this when I was in high school? (Pretty sure my dates were at the mall, the movies, and the 24-hour diner.)

Playing By Heart

This movie intertwines numerous different love stories of all kinds in all sorts of amazing ways. Angelina Jolie spends a great deal of the film aggressively throwing herself at Ryan Philippe to no avail. He finally admits that his last girlfriend gave him HIV and he will never again be capable of a relationship or love. She tearfully argues with him that he can absolutely love someone again and they kiss in her car while it’s pouring rain outside (naturally).

Save The Last Dance

Julia Stiles has had a pretty ideal fictional high school experience when it comes to boyfriends. In this movie she not only gets to be best friends with Kerry Washington-the fabulous future Olivia Pope-she dances and romances with future OP’s brother, Derek. Derek is the first person she’s able to open up to about her heartbreak and guilt over the death of her mother and her dream to attend Juilliard. He teaches her dance moves for her Juilliard audition, takes her to the ballet and they share an incredibly romantic kiss at the end of the night.

The Spectacular Now

Shailene Woodley seems to be the new contender for most swoon-inducing high school romances, and her scene with Miles Teller in this flick depicts some very realistic sweet first kiss innocence. It’s just one long continuous take of the two of them walking together, where it’s clear that Teller’s character is not used to sensitive, down to earth girls and Woodley’s character is still baffled by his apparent interest in her. The walk ends with a fantastically (spectacularly?) sweet, awkward kiss between them that solidifies that these two opposites might just belong together.

Imagine Me and You

This film takes us through the love story of two women, Rachel (Piper Perabo) and Luce (Lena Headey). They meet on Rachel’s wedding day, marrying a man and not having even realized herself that she’s actually attracted to women. Luce and Rachel immediately bond and become fast friends, although Luce—openly identifying as a lesbian—is painfully aware of her passionate feelings for Rachel, but knows she can’t and shouldn’t break up a marriage. Later, Rachel finally admits that she’s in love with Luce, leading to a highly-anticipated kiss in her flower shop. Bonus? The two of them have an incredible night playing Dance Dance Revolution at an arcade that’s equally as adorable as their first kiss.

Now and Then

Christina Ricci is the tough tomboy Roberta and Devon Sawa is Scott of the dreaded Wormer family, who constantly taunts and pranks all of Roberta’s friends. One night, Scott comes across Roberta shooting hoops by herself and they tentatively agree to a truce after playing some one on one. Scott then nervously mumbles/asks if he can kiss her. She anxiously agrees and they share the sweetest kiss that two awkward teenagers have ever had in the history of pubescent romance.

(Images via, via, via, via, via, via, via, via, via, via, via, via.)

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