30 Movies to Watch if Cuffing Season Isn’t Going as Planned

If all your hopes and dreams of doing as our lord and savior SZA suggested and finding yourself a “big boy” for cuffing season aren’t going as planned, don’t fret. We’ve all been in less-than-ideal dating situations, and could use a little encouragement to get through these potentially soul crushing times. Whether you just have to laugh at how poorly your 2023 relationship plans are going so far, you need a good cry to cleanse your soul, you’re ready to embrace being a single queen, or you want to restore you hope in love and romance, there’s a movie (or 6) for that! 

No matter how you’re feeling about the perils of dating, embrace the emotions. Another cuffing season has come just as it will pass, and we will all be better people for surviving it. If you need a way to fill your next dateless Saturday night, refer to this list for 30 movies to watch if cuffing season isn’t going as planned. 

 

 

If you need a laugh

 

How to Lose a Guy in 10 Days

Where to stream: Paramount+

If hearing “And all the girls thought that they’d be Ben’s partner, they’d be Ben’s partner…” trending on TikTok and Instagram reels puts a smile on your face, that’s a sign it’s time for a rewatch of How to Lose a Guy in Ten Days. Watch as advice columnist Andie Anderson works on a piece about making a man break up with her within ten days by doing the most outrageous things to drive him off. Meanwhile, her man of choice, Ben Berry, is on a mission of his own—to prove he can make any woman fall in love with him within ten days. Of course, chaos ensues. When you’re finished, you can day dream of your own iconic yellow dress moment. 

 

Beauty Shop

Where to stream: Prime Video

When you’re in need of a good laugh, I can’t think of anyone more capable of inflicting some giggles than Queen Latifah. After one too many run-ins with her boss, Jorge, at their hair salon, Gina has had enough. Being the exceptional hair stylist that she is, she sets out to open her own salon, even taking a few of her previous clients with her. Jorge will stop at nothing to derail her success. Gina must fight several battles she didn’t see coming, as well as navigate a new love interest she didn’t expect. 

 

John Tucker Must Die

Where to stream: Prime Video

We’ve all been there: overcome by the urge to ruin the life of the person that broke our heart. Unfortunately for us, our lives aren’t a movie and we can’t exact brutal revenge on the people who scorn us. Luckily, we can live vicariously through the gals of John Tucker Must Die who join forces to inflict the ultimate revenge on the man who cheated on all of them. 

 

About Last Night

Where to stream: Hulu

Few actors have reached the comedic level of Kevin Hart, so when you just have to laugh at the state of your love life, turn to About Last Night. Danny and Debbie’s past relationship issues have made them each skeptical about love, but neither can deny their attraction to one another. Their best friends, Bernie and Joan, try to caution them about starting a relationship, but Danny and Debbie continue to spend time together. Of course, Bernie and Joan find some trouble to get into of their own. 

 

The Proposal

Where to stream: Hulu

If seeing Sandra Bullock dancing in the woods to “Get Low” doesn’t put a smile on your face, I truly don’t know what will. The Proposal is an all-around adorable and hilarious film to throw on when you could use a laugh. When book editor Margaret Tate is threatened with deportation back to Canada, she compels her assistant to go along with the ruse that they’re engaged. Feeling obligated to go along with the scheme, he puts forth a condition—she must join him in visiting his family in Alaska. The two must play the role of the loving couple for both his family and the immigration agent on Margaret’s tail.

 

Imagine Me & You

Where to stream: Prime Video

While this movie has made our “laugh list” because you won’t be able to watch without chuckling every other minute, we should also mention there are quite a few “Aww” moments, too (so, basically the perfect movie, right?). Rachel couldn’t be more excited to marry her best friend, Heck. But as she’s walking down the aisle, she notices Luce, the wedding florist, and feels instantly drawn to her. Despite a happy marriage, Rachel can’t get Luce out of her head, and upon spending more and more time with her, Rachel feels herself starting fall. This story is complicated, heartfelt, and wildly funny—just what all of us need. 

 

If you want to embrace being single

 

How to Be Single

Where to stream: Hulu

When you’re in your anti-Valentine’s Day era, it’s important to be equipped with plenty of content to keep you feeling empowered about your singledom. Enter: How to Be Single. When Alice decides to take a break from her long term relationship to find her wings in New York City, she had no idea how much she’d learn about herself, love, and friendship. Warning: we can’t be held responsible if this movie makes you want to pack up and move to the Big Apple. 

 

Eat, Pray, Love

Where to stream: Prime Video

There’s not a movie out there that will make you want to travel quite like Eat, Pray, Love. Liz Gilbert’s world is flipped upside down after going through a divorce and she begins questioning herself and what’s important in life. Determined to reclaim her identity, she sets out on the journey of a lifetime to Italy, Bali, and India. If you can relate to going through major life changes that shake your world, press play immediately. 

 

Wild

Where to stream: Prime Video

If you’ve ever found yourself in a Lorelai Gilmore circa A Year in the Life “Summer” episode moment (IYKYK), you’re probably going to feel incredibly inspired by Wild. Cheryl has been dealing with a string of troubles, most notably, losing her mother and the end of her marriage. She realizes that she hasn’t been handling it very well, often falling into self-destructive behaviors. Fed up with her own choices, she sets out to change her life by hiking the Pacific Crest Trail, even though she has little outdoor experience. What could go wrong—or very right? 

 

The Other Woman

Where to stream: HBO Max

Nicki Minaj’s cameo in this movie is just the icing on top of an all around great cinematic experience. Against her better judgement, Carly Whitten, a successful New York lawyer, falls for a handsome man named Mark King. Little does she know, Mark is married to a woman named Kate. When the two find out about one another, they cultivate a hatred of Mark. That is until they learn of a third woman involved in Mark’s life and the trio join forces to seek revenge. 

 

Waiting to Exhale

Where to stream: Prime Video

The cast of Waiting to Exhale is basically the dream team of female empowerment, and we know you’ll end this movie feeling more confident than ever before (and not just because of the car scene—if you know, you know). The theme of this movie is one we can all relate to, and it’s a film that will make us more thankful than ever for our girlfriends. Four women lean on one another as they navigate life and deal with the failures of their love lives.

 

Under the Tuscan Sun

Where to stream: Prime Video

We’ve all been there—having the undeniable urge to leave everything behind and start over in a foreign country. Frances Mayes does just that after divorcing her cheating husband. When her friends send her on a tour of Italy, she impulsively decides to stay, purchase a rural villa, and start over. This movie is the perfect reminder that when your life gets turned upside down, you’re in the perfect place for redirection. 

 

If you want to feel hopeful about love

 

To All the Boys I’ve Loved Before

Where to stream: Netflix

If you ask me, looking at Noah Centineo’s face for an hour and a half is enough to restore anyone’s hope in love, but if you require a little bit more, this movie delivers. Lara Jean’s world collapses when she realizes the five love letters she wrote for each one of her crushes that were never supposed to see the light of day were mailed out to the boys. What seems like the end of her young world may just open more doors than she ever could have imagined. 

 

10 Things I Hate About You

Where to stream: Disney+

In a movie based on Shakespeare’s classic tale, Taming of the Shrew, you know you’re in for an epic love story (and, in this case, a lot of laughs). Kat and her sister Bianca could not be more different—Kat wants nothing to do with the nauseating boys at her high school, while Bianca is begging to be able to go on a date. But, per their father’s rules, Bianca can only date when Kat does. Bianca and her suitor come up with a master plan to get Kat on the market. 

 

He’s Just Not That Into You

Where to stream: Hulu

In He’s Just Not That Into You, 20 and 30 somethings in Baltimore navigate their struggles with love. When Gigi, who is desperate to find “the one,” meets cute bartender, Alex, he lets her in on a little secret: if a man wants to be with you, he will make it happen. With this life changing knowledge in mind, she sets out to conquer the dating world. This movie will leave you hopeful that, to someone out there, you are the exception to the rule. 

 

Love, Simon

Where to stream: Hulu

As if navigating puberty isn’t difficult enough, Love, Simon perfectly captures the added pressures of life as a teen keeping their sexuality a secret. When he begins an online relationship with a boy at school who also hasn’t come out yet, it proves to be a life-changing experience. There’s always something special about a coming-of-age story, and this one tugs on the heartstrings in a special way, providing everything you could hope for in a movie. With Love, Simon you’re in for plenty of giggles, a tear or two, and all the feels. 

 

Friends With Benefits

Where to Stream: HBO Max

If you’ve never wanted to participate in a flash mob before, allow this movie to change your mind. It may discourage you from attempting to navigate a FWB relationship, however, but, a win is a win. Jamie is a recruiter in New York City tasked with convincing Dylan, an art director, to leave the slow pace of Los Angeles life for a job in the bustling Big Apple. The two become fast friends, and upon learning that they’ve each had a string of bad luck in the love department, they agree to start a sexual relationship with no strings attached. 

 

Valentine’s Day

Where to stream: HBO Max

Just in time for the most romantic holiday of the year, rewatch Valentine’s Day for a little bit of hope for the future. Over the span of one Valentine’s Day, watch as several Los Angeles hopefuls navigate love in stories that connect with one another in the most unexpected and heartwarming ways. 

 

If you need a reminder of what romance looks like

 

Pride and Prejudice

Where to stream: Prime Video

No one has captured love quite like Jane Austen, and this adaptation of her acclaimed novel is beautiful enough to restore anyone’s belief in romance. Elizabeth Bennett is the oldest sister in her family, meaning she feels the most pressure to marry. When she meets Mr. Darcy, she quickly falls head over heels. Don’t be alarmed if this movie gets your heart racing a time or two. 

 

The Notebook

Where to stream: Prime Video

Perhaps the modern day Jane Austen, Nicholas Sparks also knows a thing or two about crafting the perfect love story. When Noah and Allie meet one summer, the two become inseparable. Her family doesn’t approve of the match as he is from a lower class in society. After being forced to separate, time and space allows Allie to somewhat move on. Noah, however, spends his life remembering her and waiting for her to come back to him. 

 

Carol

Where to stream: Prime Video

If you could use a reminder that love does, in fact, conquer all, head to Prime Video to watch Carol ASAP. Set in the 1950s, a young photographer named Therese meets the elegant and glamorous Carol Aird as she’s shopping for a doll for her daughter. The two women form an unexpected bond that comes with even more unforeseen repercussions. We know you won’t be able to get enough of this story, so after the credits roll, pick up the book it was based off of, The Price of Salt. 

 

Love & Basketball

Where to steam: Prime Video

Romance and nostalgia go hand in hand, and Love & Basketball is one of those movies from our childhood that truly never gets old. Monica has two loves in life: basketball and Quincy, a childhood friend that becomes much more than a friend as they grow older. As they both seek to grow their career in the sport, their relationship is threatened. 

 

Say Anything

Where to stream: Hulu

It doesn’t get much more iconic love story-esque than the boombox outside of the window move. See where the ultimate romantic gesture began with Say Anything. Lloyd isn’t the only one shocked to learn that beauty queen and star student Diane shares his affections. Her father is against Diane pursuing the relationship, though, and Lloyd is forced to put in more work than he thought to win her over. 

 

Casablanca 

Where to stream: HBO Max

If we learned anything from Lorelai Gilmore (other than coffee is necessary to survive), it’s that one of the best movies ever created is Casablanca. This movie exudes romance, so it should come as no surprise that it gained a spot on our list. Rick Blaine, a nightclub owner, never expected to see his lost love Ilsa again. That is until Ilsa and her revolutionist husband show up at his doorstep in trouble asking for his help to get them out of the country. Do Lorelai proud while watching this one by having way too many snacks and minimizing all distractions. 

 

If you just want to cry for a bit

 

Inside Out

Where to stream: Disney+

While not exactly a love story, I’ve yet to find a movie that can make me cry quite like Inside Out—it’s literally all about emotions. 11-year-old Riley from the Midwest struggles to deal with her family moving to San Francisco. Her emotions aim to help guide her through the life changing event. When you’re ready to let it all out, Disney+ is the place to go. 

 

The Fault in Our Stars

Where to stream: HBO Max

Gus and Hazel meet and quickly bond over two things: their favorite author, Peter Van Houten, and cancer. The more time they spend together, the closer they get and inevitably fall in love. When Gus is invited to meet the author, he and Hazel plan to share the experience with one another. Be sure to have a Kleenex box or two on hand while watching this one. 

 

Portrait of a Lady on Fire

Where to stream: Hulu

Something about 18th century France screams romance these days, but Héloïse, who has just left the convent and is preparing for marriage, couldn’t be more reluctant about her impending nuptials to a nobleman. A painter named Marianne is hired to create a portrait of Héloïse, but quickly learns it will be no simple task as her subject refuses to pose. Instead, Marianne must accompany Héloïse on her daily activities and observe her enough to create the portrait. Neither of the women know just how much their time together will mean to both of them. 

 

Titanic

Where to stream: Paramount+

This wouldn’t be a well rounded list without including one of the greatest love stories of all time. Based on the tragic event that shook the world in 1912 comes the epic love story of Rose and Jack. A member of high society, Rose’s life has been planned out for her to a T. When she meets Jack, a struggling artist who had to gamble his way onto the ship, she quickly falls in love with his free spirit and the life they could create together before tragedy strikes. 

 

My Girl

Where to stream: Netflix

When the major setting of a movie is a funeral home, there’s bound to be a tear or two shed. Vada Sultenfuss isn’t your typical 11-year-old girl. For one, her mom died giving birth to her and her father runs a funeral home out of their house—giving her a bit of a morbid curiosity in life. It also doesn’t help that her best friend is a boy with plenty of problems of his own, who happens to be the only one who accepts her for who she is. If the song “My Girl” alone could make you cry, brace yourself for this tear jerker.

 

If Beale Street Could Talk

Where to stream: Netflix

Set in 1970’s Harlem, Tish and Fonny couldn’t be more in love and excited to plan for their upcoming wedding and their growing family. Their plans are hindered when Fonny is arrested for a crime he didn’t commit. Left to handle her pregnancy and life on her own, Tish and her family dedicate themselves to proving Fonny’s innocence. Based on the novel by praised author James Baldwin, this is a story for the ages. 


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