What would romantic comedies be without the charming and insightful sidekicks who offer unwavering support for the frequently conflicted leads? The road to finding true love is seldom smooth and steady, and when our heroes and heroines need a shoulder to cry on or a soft place to land, best friends are waiting to pick up the pieces. Whether these pals use humor to lighten a situation, offer profound wisdom, or just simply a sympathetic ear and box of tissues, their role in romantic comedies is profound and greatly underappreciated.

The film genre has been one of the most successful in cinema history, gaining steam in Hollywood during the 1930s and ‘40s and remaining a staple throughout the decades, with a resurgence once again in the 1990s with classics like Sleepless in Seattle, Four Weddings and a Funeral, and My Best Friend’s Wedding. Many of the silver screen’s biggest and most gifted talents have appeared in romantic comedies, and big names like Whoopi Goldberg, Carrie Fisher, and Phillip Seymour Hoffman have taken on the supporting role of the trusty best friend for these endearing flicks.

Whether encouraging the leads to be the star of their own lives, pretending to be a psychiatrist for the sake of a juicy column, or reminding them of their goals and overall self-worth, rom-com sidekicks are truly a lively and absorbing bunch. These were the most memorable 'best friends' in romantic comedies.

Update November 10, 2023: This article has been updated with more great romantic comedy best friends and where each of the films can be streamed.

8 Delilah (How Stella Got Her Groove Back)

How Stella Got Her Groove Back
20th Century Fox

The 1998 romantic dramedy How Stella Got Her Groove Back follows the successful forty-something San Francisco stockbroker Stella Payne, who is persuaded by her spirited best friend Delilah to take a much-deserved first-class vacation to Jamaica. While there, she finds herself in a blossoming romance with the handsome young islander Winston Shakespeare, who is 20 years her junior.

What Makes Them Great

The film stars Angela Bassett and Taye Diggs as the sizzling budding couple, with Whoopi Goldberg portraying Stella’s close confidant, Delilah, who encourages her to embrace life to the fullest and reminds her gal pal that she deserves to let loose and have some fun. Delilah is without a doubt the reason Stella was able to get her groove back and provided much appreciated comedic relief for both the characters and audiences watching. For her performance as the colorful and amusing Delilah, Goldberg won the NAACP Images Award for Outstanding Supporting Actress in a Motion Picture.

Rent/Buy on Prime Video

7 Duckie (Pretty in Pink)

Pretty in Pink
Paramount Pictures

Beloved filmmaker John Hughes wrote the classic 1986 teen romantic comedy Pretty in Pink, featuring his frequent collaborator and muse Molly Ringwald, Jon Cryer, and Andrew McCarthy. The flick centers on high school senior and perpetual outcast Andie Walsh (Ringwald), who must choose between dating her childhood best friend Duckie (Cryer) or the rich-yet-kind Blane (McCarthy). Andie is completely oblivious to the fact that Duckie is head-over-heels in love with her, as she finds herself smitten with Blane.

What Makes Them Great

Duckie is devoted to his best friend and is always there for Andie, even taking her to the prom when her relationship with the other suitor deteriorates. Originally, Pretty in Pink portrayed childhood friends ending up together, but test audiences booed this ending. Even Ringwald was in favor of her character and Blane winding up together, having retrospectively said, “It didn’t make sense to have the entire movie be this Cinderella story [yet] she doesn’t get to end up with the guy she wants.”

Stream on Max

Related: Best John Hughes Movies, Ranked

6 Michelle (How to Lose a Guy in 10 Days)

Kathryn Hahn in How to Lose a Guy in 10 Days
Paramount Pictures

Donald Petrie’s 2003 box office hit How to Lose a Guy in 10 Days stars Matthew McConaughey, and hilariously follows advice columnist Andie Anderson (Kate Hudson), who decides to push boundaries and write a piece about getting a man to leave someone in 10 days. She sets her sights on advertising executive and all-around ladies man Ben Barry, who is so confident in his romantic prowess that he believes he can make a woman fall for him in 10 days. Neither party realizes just what chaos and hijinks are in store for them.

What Makes Them Great

Andie’s best friend Michelle (the always scene-stealing Kathryn Hahn) has a bit of a chaotic love life herself, which the former uses as inspiration to craft her edgy and out-of-the-box column. Michelle also memorably (and amusingly) pretends to be a couples’ therapist, encouraging the dysfunctional couple to take the next step and have Andie meet Ben’s family on Staten Island. Though a kind yet all-around hot mess, Michelle keeps her hopeless romantic mind frame and changes Andie’s outlook on love at the same time.

Stream on Paramount+

5 Arthur (The Holiday)

Arthur Abbott & Iris Simpkins in The Holiday
Sony Pictures Releasing

Nancy Meyers’ adored 2006 Christmas staple The Holiday tells the story of two lovelorn women on opposite sides of the world who decide to arrange a home exchange in order to escape their respective heartbreak during the festive holiday season. The film features an impressive cast of Hollywood heavy hitters, including Cameron Diaz, Kate Winslet, Jude Law, and Jack Black. When Iris Simpkin (Winslet) arrives in Los Angeles to get over being lovesick for her ex, she meets her charming and spirited next-door neighbor Arthur Abbott (Eli Wallach), an elderly Oscar-winning screenwriter from the Golden Age of Film.

What Makes Them Great

The unlikely friendship is everything Iris needs and more, as Arthur, poignantly reminds her, “In the movies, we have leading ladies, and we have the best friend. You, I can tell, are a leading lady, but for some reason, you’re behaving like the best friend.” The duo is supportive of one another throughout the whole picture, with Iris encouraging Arthur to overcome his self-consciousness and attend a ceremony in his honor and Arthur pointing out that she deserves nothing but the very best.

Stream on Hulu

Related: These Are the Best Nancy Meyers Films as Both a Writer and Director, Ranked

4 Marie (When Harry Met Sally…)

Carrie Fisher in When Harry Met Sally
Columbia Pictures

Rob Reiner’s iconic romantic comedy When Harry Met Sally… famously depicts the title characters who share a combative car ride from Chicago to New York in 1977, fiercely discussing whether men and women can ever be strictly platonic friends or not. The former college graduates meet once again five and then ten years later in a bookstore and attempt to stay friends without complicating their relationship with sex. Billy Crystal and Meg Ryan famously lead the flick, with Bruno Kirby and Carrie Fisher serving as the characters’ respective best friends.

What Makes Them Great

Fisher portrays Marie, who constantly pep-talks her pal while offering ridiculously funny commentary and a constant shoulder to lean on. She is a calming presence for Sally and has no problems putting the character’s woes in perspective. When Harry Met Sally is widely considered one of the best and most beloved romantic comedies of all time, and the picture’s extraordinary cast and characters remain some of cinema’s greatest.

Stream on Paramount+

3 Sandy (Along Came Polly)

Along Came Polly
Universal Pictures 

Ben Stiller and Jennifer Aniston proved to be comedy gold on the big screen when they appeared together in the 2004 hit Along Came Polly. The flick follows the risk-averse Reuben Feffer, who reconnects and falls in love with the free-spirited Polly, his former classmate. Phillip Seymour Hoffman steals the show as the washed-up former child actor Sandford “Sandy” Lyle, who, despite his best intentions, offers Reuben terrible advice that often leads to mayhem. The crude, has-been character is given his own storyline and journey for the rom-com as he comes to terms with his floundering Hollywood career.

What Makes The Great

Sandy is a dutiful side-kick who will do anything to help Reuben out of a jam, including filling in for his buddy at work by giving a sidesplitting and rousing speech about a client that is full of passionate nonsense. The Herald Sun raved about the scene-stealing character, writing, “Worth a look if you’re after easy laughs, many of which come from Phillip Seymour Hoffman as Stiller’s right-hand buffoon.” The legendary actor was iconic for his serious and intense performances but is just as magnetic and mesmerizing in funnier roles like this.

Stream on Peacock

2 Penny (The Wedding Planner)

Judy Greer & Jennifer Lopez in The Wedding Planner
Sony Pictures Releasing 

Adam Shankman’s delightful 2001 romantic comedy The Wedding Planner focuses on ambitious San Francisco wedding planner Mary Fiore, who knows all the tried and true tricks and to successfully staging a wedding; she breaks the cardinal rule, though, when she unknowingly falls for the groom of her most important and lucrative account yet. Jennifer Lopez portrays the resourceful Mary, with Matthew McConaughey starring as the handsome pediatrician and husband-to-be Steve Edison.

What Makes Them Great

Famed character actress Judy Greer is Mary’s right-hand-woman and close friend, Penny Nicholson, who constantly pushes Mary to put herself first and embrace the dreams that she rightly deserves. She is a kind and supportive cheerleader for Mary and a calming presence, stepping up for her friend repeatedly throughout the film. Judy Greer has perfected the 'best friend' role in a slew of romantic comedies, but Penny is undoubtedly her most endearing and lovable character.

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1 George (My Best Friend’s Wedding)

Rupert Everett in My Best Friend's Wedding
Sony Pictures

Considered one of the greatest and most successful romantic comedies in all cinema, 1997’s My Best Friend’s Wedding follows New York City food critic Jules as she comes to the stunning realization that she’s in love with her longtime friend Michael when he announces his engagement. The film famously stars Julia Roberts, Dermot Mulroney, Cameron Diaz, and Rupert Everett and details Jules’ frantic effort to stop the wedding and proclaim her feelings for Michael. Everett stars as Jules’ gay friend and editor, George Downes, who agrees to pretend to be engaged to her in an effort to make Michael jealous.

What Makes Them Great

George is the voice of reason in the picture, continuously reminding Jules that trying to steal Michael away from his fiancé is devious and deplorable, and warns her that it will inevitably not end well. Everett completely captured audiences by getting everyone in a seafood restaurant to boldly sing “I Say a Little Prayer” and remained a stable presence for Jules, showing up at the end to dance with and console the broken-hearted heroine. He's often the template for rom-com best friends today.

Stream on Netflix