Movies Like The Upside of Unrequited

If you liked The Upside of Unrequited, a romance and comedy movie directed by Hillary Shakespeare and Anna-Elizabeth Shakespeare, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Relationship Goals (2026)
★ 6.4/10Also romance and comedy
When TV producer Leah Caldwell aims to become the first woman running New York's top morning show, her ex competes for the same role. Leah stays focused on her career, until chemistry with her ex challenges her…
2
Boot Camp (2024)
★ 6.1/10Also romance and comedy
Unathletic Whitney Carmichael signs up for an intense summer boot camp to reinvent herself and falls for her personal trainer. She then finds the strength to embrace her true self and ignore the others' expectations.
3
Love Is in the Air (2023)
★ 6.2/10Also romance and comedy
A fiercely independent pilot fighting to keep her family business afloat starts to fall for the man sent by corporate to ground her operation forever.
4
¿Quieres ser mi hijo? (2023)
★ 8.4/10Also comedy and romance
Lu, a conformist woman in her forties, learns that her 15-year partner has been having extramarital affairs. Starting from scratch, she gets involved in an unexpected relationship with a young womanizer.
5
What's Love Got to Do with It? (2023)
★ 6.1/10Also romance and comedy
Two childhood friends now in their thirties must decide whether to follow their heads or their hearts once the man decides to follow his parents' advice and enter into an arranged marriage in Pakistan.
6
How I Got Into College (1989)
★ 6/10Also comedy and romance
High school senior Marlon Bowne is smitten with overachieving classmate Jessica Kailo. But, if he wants to have a shot with her, he'll have to find a way to get into Ramsey College, Jessica's top choice of schools. It…
7
To All the Boys I've Loved Before (2018)
★ 7.6/10Also comedy and romance
Lara Jean's love life goes from imaginary to out of control when her secret letters to every boy she's ever fallen for are mysteriously mailed out.
8
The Kissing Booth 2 (2020)
★ 7.6/10Also comedy and romance
With college decisions looming, Elle juggles her long-distance romance with Noah, changing relationship with bestie Lee and feelings for a new classmate.
9
Yoh! Bestie (2026)
★ 6.2/10Also romance and comedy
Thando is perpetually unlucky in love, but when her bestie returns from his travels with a fiancée in tow, she's forced to face a new emotion — jealousy.
10
Love, Weddings & Other Disasters (2020)
★ 6/10Also romance and comedy
A fussy celebrity caterer, a blind woman, a tour-bus guide and an inexperienced wedding planner search for love.
11
The Prince & Me 4: The Elephant Adventure (2010)
★ 6.1/10Also comedy and romance
One year after their royal wedding, King Edvard and Queen Paige of Denmark receive an invitation to attend the wedding of Princess Myra of Sangyoon. Upon their arrival, Paige finds Myra is unhappy with her arranged…
12
The List (2023)
★ 5.9/10Also romance and comedy
After her fiance sleeps with a celebrity on his free pass list, Abby Meyers, with nothing but five names and a fantasy shared by millions, sets out for Los Angeles to sleep with someone from hers.
13
The Kissing Booth (2018)
★ 7.2/10Also romance and comedy
When teenager Elle's first kiss leads to a forbidden romance with the hottest boy in high school, she risks her relationship with her best friend.
14
The Kissing Booth 3 (2021)
★ 6.8/10Also romance and comedy
It's the summer before Elle heads to college, and she has a secret decision to make. Elle has been accepted into Harvard, where boyfriend Noah is matriculating, and also Berkeley, where her BFF Lee is headed and has to…
15
Dinner in America (2022)
★ 7.8/10Also romance and comedy
An on-the-lam punk rocker and a young woman obsessed with a local band go on an unexpected and epic journey together through the decaying suburbs of the American Midwest.
16
A Nice Girl Like You (2020)
★ 5.8/10Also comedy and romance
Lucy Neal is thrown for a loop when she is accused of being too inhibited by her ex-boyfriend. In an effort to prove him wrong, Lucy creates a rather wild to-do list that sends her on a whirlwind and surprising journey…
17
Hot Frosty (2024)
★ 5.9/10Also romance and comedy
When a young widow's magic scarf brings a dashing snowman to life, can he help her rediscover romance, laughter and holiday cheer before he melts away?
18
Christmas with You (2022)
★ 5.8/10Also romance and comedy
Feeling career burnout, pop star Angelina escapes to grant a young fan's wish in small-town New York, where she not only finds the inspiration to revitalize her career but also a shot at true love.
19
Your Christmas or Mine? (2022)
★ 6.4/10Also comedy and romance
Students Hayley and James are young and in love. After saying goodbye for Christmas at a London train station, they both make the same mad split-second decision to swap trains and surprise each other. Passing each…
20
All Over the Guy (2001)
★ 5.9/10Also comedy and romance
A contemporary romantic comedy exploring the unlikely pairing of two 20-somethings thrown together by their respective best friends in hopes of igniting their own romance.