Movies Like Sierra Burgess Is a Loser

If you liked Sierra Burgess Is a Loser (2018), a comedy and drama movie directed by Ian Samuels, 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
10 Things I Hate About You (1999)
★ 7.6/10Also comedy and romance
After discovering his high school crush can't date until her brash older sister does, a lovesick teen enlists a bad-boy classmate to woo her.
2
John Tucker Must Die (2006)
★ 6.1/10Also comedy and romance
After discovering they are all dating the same same guy, three popular students from different cliques band together for revenge, so they enlist the help of a new gal in town and conspire to break the jerk's heart…
3
He Said, She Said (1991)
★ 5.9/10Also comedy and drama
Womanising, right-wing Dan Hanson and quiet, liberal Lorie Bryer work for the Baltimore Sun. Rivals for the job of new writer of a vacant column, the paper ends up instead printing their very different opinions…
4
The Best of Me (2014)
★ 7.5/10Also drama and romance
A pair of former high school sweethearts reunite after many years when they return to visit their small hometown.
5
The Half of It (2020)
★ 7.1/10Also comedy and romance
Shy, straight-A student Ellie is hired by sweet but inarticulate jock Paul, who needs help wooing the most popular girl in school. But their new and unlikely friendship gets tricky when Ellie discovers she has feelings…
6
Drive Me Crazy (1999)
★ 6.6/10Also romance and comedy
Nicole and Chase live next door to each other but are worlds apart. However, they plot a scheme to date each other in order to attract the interest and jealousy of their respective romantic prey. But in the mist of…
7
The Wrong Paris (2025)
★ 6.7/10Also romance and comedy
Dawn thinks she's joining a dating show in Paris, France, only to land in Paris, Texas. She has an exit plan — until sparks fly with the cowboy bachelor.
8
Twelfth Night (1996)
★ 7/10Also drama and comedy
Shakespeare's comedy of gender confusion, in which a girl disguises herself as a man to be near the count she adores, only to be pursued by the woman he loves.
9
The Prom (2020)
★ 6.1/10Also romance and comedy
After the PTA of a conservative high school in Indiana bans same-sex couples from attending the annual prom, a gang of flamboyant Broadway stars try to boost their image by showing up to support two lesbian students.
10
The DUFF (2015)
★ 6.8/10Also romance and comedy
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…
11
Sidewalks of New York (2001)
★ 6.1/10Also comedy and drama
The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with scenes from the six characters' lives…
12
A California Christmas (2020)
★ 6.4/10Also comedy and romance
With his carefree lifestyle on the line, a wealthy charmer poses as a ranch hand to get a hardworking farmer to sell her family’s land before Christmas.
13
Which Brings Me to You (2023)
★ 6.3/10Also romance and comedy
Two romantic burnouts, Jane and Will, are immediately drawn to each other at a mutual friend’s wedding. After a disastrous hookup in the coatroom, the two spend the next 24 hours together, trading candid confessions of…
14
Love in Taipei (2023)
★ 6.8/10Also romance and comedy
A young American woman is sent by her parents to a cultural immersion program in Taipei where she begins a new journey of self-discovery and romance.
15
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…
16
Bridget Jones: Mad About the Boy (2025)
★ 6.3/10Also romance and comedy
Bridget Jones navigates life as a widow and single mum with the help of her family, friends, and former lover, Daniel. Back to work and on the apps, she's pursued by a younger man and maybe – just maybe – her son's…
17
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.
18
Endless Love (2014)
★ 6.9/10Also drama and romance
A privileged girl and a charismatic boy's instant desire sparks a love affair made only more reckless by parents trying to keep them apart.
19
You Will Meet a Tall Dark Stranger (2010)
★ 5.9/10Also comedy and drama
Two married couples find only trouble and heartache as their complicated lives unfold. After 40 years of marriage, Alfie leaves his wife to pursue what he thinks is happiness with a call girl. His wife, Helena, reeling…
20
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.