He’s Just Not That Into You (2009): A Star-Studded Rom-Com Exploring Love and Miscommunication

Released on February 6, 2009, He’s Just Not That Into You is a romantic comedy-drama directed by Ken Kwapis, adapting the bestselling self-help book by Greg Behrendt and Liz Tuccillo. Boasting an ensemble cast including Jennifer Aniston, Ben Affleck, Scarlett Johansson, Drew Barrymore, and Bradley Cooper, the film weaves interconnected stories of love, rejection, and modern relationships in Baltimore. Produced by New Line Cinema and Flower Films, it grossed $178.8 million worldwide against a $40 million budget, despite mixed reviews with a 40% Rotten Tomatoes score. Celebrated for its relatable characters and sharp dialogue, yet critiqued for its uneven tone, He’s Just Not That Into You remains a notable entry in the 2000s rom-com resurgence. This article explores the film’s origins, creative team, plot, production, critical response, and lasting legacy.

Origins and Inspiration

He’s Just Not That Into You began as a 2004 self-help book by Greg Behrendt, a consultant on Sex and the City, and Liz Tuccillo, a writer for the series. Inspired by a Sex and the City episode where Miranda learns a man’s lack of follow-through signals disinterest, the book offers blunt dating advice for women, encapsulated in its title. Its candid approach—urging readers to recognize when a partner isn’t invested—struck a chord, selling over two million copies and prompting a film adaptation. New Line Cinema acquired the rights, with Drew Barrymore’s Flower Films producing and Ken Kwapis, known for The Sisterhood of the Traveling Pants (2005), directing.

The film diverges from the book’s advice format, crafting a narrative around multiple characters navigating love’s complexities. Screenwriters Abby Kohn and Marc Silverstein, with input from Tuccillo, transformed the book’s concepts into a mosaic of interlocking stories, blending humor with emotional depth. The project attracted a stellar cast, leveraging the star power of Aniston, Affleck, and others to appeal to a broad audience during the rom-com boom of the late 2000s, alongside films like The Proposal and Valentine’s Day.

Plot and Structure

Set in Baltimore, He’s Just Not That Into You follows nine characters whose romantic lives intertwine, exploring themes of miscommunication, commitment, and self-worth. The film’s ensemble structure, reminiscent of Love Actually (2003), weaves multiple storylines:

• Gigi (Ginnifer Goodwin): A naive single woman obsessed with decoding men’s signals, Gigi misinterprets dates until bar owner Alex (Justin Long) offers blunt advice, sparking an unexpected attraction.
• Beth (Jennifer Aniston) and Neil (Ben Affleck): In a long-term relationship, Beth pushes for marriage, while Neil resists commitment, leading to a breakup and eventual reconciliation.
• Janine (Jennifer Connelly) and Ben (Bradley Cooper): Married but strained, Ben’s affair with aspiring singer Anna (Scarlett Johansson) threatens their stability, while Janine grapples with betrayal.
• Anna and Conor (Kevin Connolly): Conor pines for Anna, who is drawn to Ben, creating a love triangle marked by mixed signals.
• Mary (Drew Barrymore): A marketing exec navigating online dating, Mary connects with Conor, finding clarity amid romantic confusion.

The film uses Gigi’s journey as a narrative anchor, with Alex’s advice echoing the book’s mantra: if a man isn’t calling or committing, “he’s just not that into you.” Intertitles and mock-interview segments with unnamed characters punctuate the stories, offering humorous insights into dating pitfalls. Set against Baltimore’s urban backdrop, the film blends comedic mishaps—like Gigi’s awkward voicemails—with poignant moments, such as Beth’s realization of Neil’s devotion. The 129-minute runtime balances each arc, though some critics found the sprawling cast diluted emotional depth.

Creative Team and Cast

Directed by Ken Kwapis, whose TV credits include The Office and Freaks and Geeks, He’s Just Not That Into You showcases a polished yet accessible style. The ensemble cast is a major draw:

• Ginnifer Goodwin shines as Gigi, bringing earnest vulnerability to her misguided romantic quests.
• Jennifer Aniston delivers a grounded Beth, balancing strength and longing in her push for commitment.
• Ben Affleck portrays Neil with quiet charm, grounding the film’s emotional core.
• Bradley Cooper and Jennifer Connelly add complexity to Ben and Janine’s crumbling marriage, with Cooper’s pre-Hangover charisma standing out.
• Scarlett Johansson sizzles as Anna, embodying temptation and ambition.
• Justin Long steals scenes as Alex, blending cynicism with warmth.
• Drew Barrymore, also a producer, offers a relatable Mary, while Kevin Connolly adds humor as the lovesick Conor.

Cinematographer John Bailey captures Baltimore’s vibrant streets and cozy interiors, enhancing the rom-com aesthetic. The soundtrack, featuring The Ting Tings’ “Fruit Machine” and Corinne Bailey Rae’s “I’d Like To,” complements the film’s upbeat tone, with Keb’ Mo’s cover of “You Really Got a Hold on Me” underscoring key emotional beats. Costume designer Shay Cunliffe outfits the cast in 2000s chic, from Gigi’s quirky dresses to Anna’s sultry looks, reflecting their personalities.

Production Details

Development began in 2007, with filming taking place in Baltimore and Los Angeles in 2008. The $40 million budget supported a high-profile cast and urban settings, with Flower Films ensuring a female-driven perspective. Kwapis aimed for a balance of humor and heart, drawing from Sex and the City’s witty realism while avoiding sitcom clichés. The script underwent revisions to flesh out the book’s concepts into character-driven stories, with Barrymore’s input shaping Mary’s arc to reflect the rise of online dating.

The film’s PG-13 rating allowed mild innuendo and language, appealing to a wide audience. Challenges included managing the ensemble’s schedules and ensuring each storyline felt cohesive. Kwapis used Baltimore’s distinct neighborhoods—like Fells Point and Mount Vernon—to ground the film’s setting, contrasting the characters’ emotional chaos with a vibrant cityscape. Post-production included trimming subplots to maintain pacing, though some fans later called for an extended cut to restore minor scenes.

Critical Reception and Controversy

He’s Just Not That Into You received mixed reviews, earning a 40% Rotten Tomatoes score based on 179 reviews. Critics praised the cast’s chemistry and the film’s relatable premise but criticized its sprawling narrative and uneven tone. The New York Times’ A.O. Scott called it “a likable mess,” noting its charm but faulting its lack of focus, while Entertainment Weekly’s Lisa Schwarzbaum gave it a B+, applauding its “shrewd observations” on dating. Ginnifer Goodwin and Justin Long earned praise for their authentic dynamic, though some felt the star-heavy cast overshadowed quieter moments.

Controversy arose over the film’s adaptation of the book’s feminist-leaning advice. Some critics, like The Guardian’s Peter Bradshaw, argued it softened the book’s bluntness, presenting women as overly hopeful romantics, particularly in Gigi’s arc. Others, including fan discussions on X from 2009, defended the film’s nuanced portrayal of relationships, appreciating its acknowledgment of both genders’ dating struggles. The mock-interview segments divided audiences, with some finding them insightful and others gimmicky. Box office success—$178.8 million worldwide—proved its commercial appeal, peaking at #1 in the U.S. during Valentine’s Day weekend.

Themes and Interpretation

The film explores modern romance through themes of miscommunication, self-worth, and the search for connection in a digital age. Drawing from the book’s central thesis, it critiques the tendency to overanalyze romantic signals, urging characters like Gigi to value themselves over unreciprocated affection. The ensemble structure highlights diverse relationship dynamics—marriage, infidelity, casual dating—reflecting the complexities of love in the 2000s. Beth and Neil’s arc champions commitment without societal pressure, while Ben and Janine’s story exposes the pain of betrayal.

The film’s Baltimore setting adds a grounded, everyman quality, contrasting the glitz of typical rom-com locales like New York. Its 2000s context, with references to MySpace and flip phones, captures a transitional era in dating technology, embodied by Mary’s online struggles. Some critics, like Variety’s Todd McCarthy, saw it as a feminist critique of chasing uninterested partners, though others felt it leaned too heavily on rom-com tropes, resolving conflicts too neatly.

Legacy and Reappraisal

Over a decade later, He’s Just Not That Into You enjoys a nostalgic cult following, particularly among fans of 2000s rom-coms. Its ensemble format influenced later films like Valentine’s Day (2010) and New Year’s Eve (2011), cementing the multi-narrative trend. The film’s relatable themes resonate with audiences navigating modern dating apps, as seen in X posts revisiting its advice in the context of Tinder and Bumble. Streaming on platforms like Max and Netflix, it remains a go-to for romantic comedy fans, with Goodwin and Long’s chemistry often cited as a highlight.

The film’s cultural impact lies in its popularization of the phrase “he’s just not that into you,” which entered the dating lexicon, sparking discussions on self-respect and relationship clarity. While no sequel was produced, the book inspired a 2009 TV special and ongoing self-help discourse. Reappraisals, like a 2019 Vulture article, praise its ensemble cast and realistic portrayal of dating woes, though some note its dated gender dynamics. The Blu-ray includes deleted scenes, such as extended Gigi-Alex moments, fueling fan interest in a fuller cut.

In the rom-com genre, He’s Just Not That Into You stands out for its ambitious cast and attempt to modernize self-help advice for the screen. While not as iconic as When Harry Met Sally, its blend of humor, heart, and star power ensures its place in the 2000s rom-com canon.

Conclusion

He’s Just Not That Into You (2009) is a vibrant, if imperfect, romantic comedy that captures the messy realities of modern love. Directed by Ken Kwapis and anchored by a stellar ensemble, it transforms a self-help book into a tapestry of interconnected stories, blending humor with poignant insights. Despite mixed reviews for its sprawling narrative, its commercial success and cultural resonance—evident in its lasting catchphrase—underscore its impact. Available on streaming platforms, the film offers a nostalgic escape for fans of rom-coms and those pondering the complexities of relationships. For deeper exploration, viewers can revisit the original book or join online discussions on X, where its dating wisdom continues to spark debate.