10 Quirky Romantic Comedies from the Last Five Years

The '90s and early 2000s were the greatest time for the rom-com, creating movie stars like Julia Roberts, Meg Ryan, and Sandra Bullock, while audiences saw them fall in love in incredible, yet thrilling situations. After that time, new rom-com queens appeared (Kate Hudson, Katherine Heigl), but the genre started to become stale, and their stories were more and more incredible and wacky, so audiences stopped responding to them as much.

In the last few years, and thanks in large part to streaming, the genre is making a comeback, giving new voices their chance in the rom-com world, and that’s creating films and love stories that are much weirder, quirky, surprising, and more fun than what we’re used to. That’s a way to keep improving, evolving, and changing the genre, while still telling stories about interesting people falling in love. Here are 10 quirky romantic comedies from the last five years for you to fall in love with.

The Half of It (2020)

What if they made Cyrano de Bergerac, but modern and with a queer twist? That’s what The Half of It is, in a sentence. This time, Ellie Chu (Leah Lewis) says the words to jock Paul Munsky (Daniele Diemer) so he can talk to Aster (Alexxis Lemire). The problem is, Ellie also falls in love with her.

An Entertaining Love Triangle

This is a great romantic comedy, but it’s also an incredible story about friendship, second-generation Americans, and discovering queer identity. The three actors in the love triangle are great, creating unique characters who are all interesting in their own right, and the surprising friendship between Ellie and Paul, perfectly rendered by Lewis and Munsky, makes this movie one of a kind.

The Lovebirds (2020)

Every couple has a moment, some years in, when they might be getting a bit tired of their routine together and must decide if they'll go all the way, or break up for good. That’s the moment Leilani (Issa Rae) and Jibran (Kumail Nanjiani) are in when they get mixed up in a murder mystery. That’s how The Lovebirds starts.

Great Chemistry Between the Leads

For a movie with a murder mystery, this is a laugh-out-loud kind of film, with both Rae and Nanjiani being as funny as ever, and making their characters' arcs almost as important as the funny moments. This quirky couple has their problems, but when things become serious, they’ll do anything for each other. The movie also earns points by showing a unique moment in relationships where things might start getting stale, and being more about re-falling in love than about two unknowns who meet for the first time.

Always Be My Maybe (2019)

In Always Be My Maybe, Ben (Randall Park) and Sasha (Ali Wong) reconnect after 15 years, and although it’s weird at first, they get back to their old rhythm as friends and start spending a lot of time together. That makes them start wondering if maybe now is the time for something more.

An Inclusive and Fun Comedy

The film is one of Netflix’s best romantic comedies, and the script, co-written by the two leads and Michael Golamco, is pretty incisive about love, romance, and hangups from the past, creating a great, funny, surprising movie. The film includes an incredible, crazy Keanu Reeves cameo, and makes some fun of the celebrity chef culture, while also showing as much heart as possible.

The Map of Tiny Perfect Things (2021)

The Map of Tiny Perfect Things is a time-loop story where Mark (Kyle Allen) is trapped, taking advantage of everything he already knows is going to happen. Things change when he discovers he’s not alone in the loop, and Margaret (Kathryn Newton) is in the same situation as him, so they start to hang out and discover many tiny, perfect things happening around them.

A Teenage Time Loop Rom-Com

This is a quirky love story, but it’s also a movie about grief and letting go, which is a surprise at first, but makes the loop idea much more understandable. The two leads work great together, and the many tiny, perfect things are as cute as they come. The loop idea also gives the romantic story some very different ingredients to play with than a teenage rom-com usually would, making it unique, and surprising.

Plus One (2019)

In Plus One, Alice (Maya Erskine) and Ben (Jack Quaid) are two single friends, who decide to go together to every wedding they have that year and help each other hook up with other people by being each other’s wing-person. As they spend more time together, they start to enjoy each other’s company much more than anyone they meet at those weddings.

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Unexpected Chemistry from the Leads

Erskine and Quaid don’t scream quirky rom-com when you think about them, but here, they work perfectly together, both in the dramatic, but especially in the comedic and romantic moments, making for an easy couple to root for. The film also shows why these two should do more romantic comedies, as they’re charming, lovely, and funny.

Happiest Season (2020)

Happiest Season is all about Abby (Kristen Stewart) and Harper (Mackenzie Davis), a couple who go back to their hometown for Christmas. Abby wants to propose, but when she discovers that Harper still hasn’t come out to her parents, things change.

An Instant Christmas Classic

This is a great queer rom-com, that’s also the perfect Christmas movie, full of unique, quirky characters, including the two leads, or Kristen Stewart’s sister’s characters in the movie; Alison Brie, and especially, Mary Holland (who co-wrote the script with director Clea DuVall). All the actors are great, including Aubrey Plaza, while Stewart and Davis prove they make the perfect couple for this breezy, unpredictable romantic story.

Long Shot (2019)

As weird ideas for a romantic comedy go, Long Shot is a strange one. Journalist Fred Flarsky (Rogen) is hired by an old teenage crush, Charlotte Field (Charlize Theron) to be her speechwriter while she runs for President of the United States.

An Unexpected Acting Duo

Rogen’s character might be a bit weird, but Theron and he work surprisingly well as a couple, and the actress shows she should do more comedies, as she’s more than good at them (this might’ve been the greatest comedic discovery since Rose Byrne in Bridesmaids). The story has heart, some romance, and many jokes, so it’s a shame it didn’t work better at the box office, as it should’ve been a slam dunk.

Sh*thouse (2020)

Sh*thouse is all about Alex (Cooper Raiff), a freshman in college who is feeling lonely and lost there, when he meets Maggie (Dylan Gelula), someone as lonely as him, but just a bit less lost. They talk, spend time together, laugh, have awkward moments, and something real starts to happen between them.

An Underrated College Movie

Written, directed, and starring Cooper Raiff when he was 23, this is one of the most underrated college movies of all time, and it’s a pretty naturalistic one. It’s obvious Raiff loves the Before trilogy, as the story here has some of the same patterns of starting to talk to someone and, little by little, story by story, feeling like you know them and that you fit together in your beliefs, ideas, and ways of looking at the world. Even then, Raiff (and Alex) is a quirky, strange guy, and the movie shows it, as the weird title is a perfect example of that.

Palm Springs (2020)

Palm Springs tells the story of Nyles (Andy Samberg) and Sarah (Cristin Milioti), who are trapped repeating the day of Sarah’s sister’s wedding over and over again. While being looped on the same day, they do some shenanigans, have fun, dance, fight, and fall in love.

An Even Better Time-Loop Rom-Com

It’s one of the best Groundhog Day knockoff movies, and one that uses the repeating day in even darker, crazier, ways than the Bill Murray film ever did. What also makes this movie great is how it gives autonomy to Sarah, as the second part of the film is all about her, all the time, as she wants to stop being in this loop. The two actors are great, and their chemistry is off the charts; there are many laugh-out-loud moments, and the film is surprisingly sweeter than it looks at first sight, making for a great quirky romantic comedy to watch.

Rye Lane (2023)

In Rye Lane, Dom (David Johansson) and Yas (Vivian Oparah) have both just been broken up with, although he shows his sadness much more than she does. When they meet in a unisex bathroom and spend their whole day together, the sadness starts to change and fade away.

Why Rye Lane Is the Best Quirky Romantic Comedy of the Last Five Years

The chemistry between the actors is great, as they’re the perfect yin and yang, and the direction by first-time movie director Raine Allen-Miller is perfect, setting the film's tone, themes, and visual language. Rye Lane shows a 21st-century love story in the south of London (not the classical Notting Hill or any other rich neighborhood), with a smart, fun script, and supporting characters who look like they’re living their lives normally while helping the romantic protagonists. The two lead characters are as quirky and weird as they come, and yet they fit together perfectly, and that’s the dream.

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