The Romantic Comedy Character with Your Enneagram Type

I was born in the ‘80s, which means that romantic comedies were a pretty big deal during my childhood and teen years. My weekends were often spent in a crowded theater watching Meg Ryan check her AOL inbox for a letter from Tom Hanks, Julia Roberts run away from the altar one too many times, and Alicia Silverstone’s “Cher Horowitz” fall in love with her former step-brother (a little weird maybe?).

With that in mind, I thought it would be a fun experiment to try to find iconic romantic comedy character with each of the nine Enneagram types. Do you relate to the characters I picked for you? Do you have another suggestion? Let me know in the comments!

Not sure what your Enneagram type is? Take our free questionnaire here

Estimated reading time: 16 minutes

The Romantic Comedy Character with Your Enneagram Type

Let’s start with the Enneagram Ones – Lucy Kelson and Sally

Average Enneagram One Characteristics: Ethical, strict, detail-oriented, responsible, critical, organized, judgmental, fear of being “evil” or corrupt.

What do these two characters have in common? Both types are concerned with issues of morality and strive for perfection in their lives. They’re both detail-oriented, driven, and hard-working.

Sally lives with a whole lot of “should’s” and “ought’s” in her life. She’s hard-working, attentive, critical, and embraces rules and perfection. Sure, she has a funny and warm side, but she’ll also send her food back if it isn’t exactly to her specifications. She judges people who are casual about sleeping with other people, and she loves everything to be organized, just right, and pristine. This need for perfection and this tendency towards critical behavior is characteristic of the average to unhealthy One. While they can be kind and good people, they can also be nitpicky, self-righteous, and judgmental. Although, to be fair, sometimes Harry deserved all the judgment he got.

Lucy Kelson, like Sally, is all about doing what’s right and moral and good. She wants to make a difference in the world; whether that means working as a pro bono lawyer for the Coalition for the Homeless or lobbying to protect soon-to-be-destroyed landmarks, everything about her is in pursuit of a higher ethical calling. She’s idealistic, determined, and sometimes a bit rigid. Everyone, particularly her employer, George Wade, rely on her for her keen judgment and sense of responsibility.

Find out more about Ones: Escaping the Trap of Resentment for Enneagram Ones

Enneagram Twos – Annie Reed and Cher Horowitz

Average Enneagram Two Characteristics: Generous, Attentive, Warm, Supportive, Overbearing, Need to Be Appreciated

Annie Reed from Sleepless in Seattle is honestly a little scary. And I kind of hate to use her as the Two Enneatype, because she’s such an odd character. But oh well. Here we go.

Learning of widower, Sam Baldwin’s, grief over the radio, she’s driven by an almost instinctual desire to heal his pain, seeing it as her mission to bring him happiness again. And then things get weird and obsessive. She tracks him down across the country, writes him a letter about how they should meet atop the Empire State Building, and falls hopelessly in love with him even though she’s never met him and is engaged already. Everything she does is guided by her heart, and sometimes this means that she blurs the lines between assistance and deranged meddling, showcasing the unhealthy Two’s challenge in balancing their need to be needed with respect for others’ autonomy.

Cher Horowitz, on the other hand, embodies the Two’s fear of rejection and desire to be seen as indispensable, albeit in a more lighthearted and playful way. She immediately sees how people “need” her and jumps in to “help.” Whether this means matchmaking, giving makeovers, or comforting her father, she genuinely wants to make a positive contribution in people’s lives. That said, at the same time she can be wildly immature and even manipulative when she doesn’t get her way or feels unappreciated. She also tends to be overly dramatic and can fall into the trap of using flattery to get what she wants. Like most Twos, she wants to be seen for the generous, selfless person she aims to be and it makes her furious when she feels misunderstood (“Like Josh thinking I was mean was making me postal.”) Overall, if you’re looking for an exaggerated and comedic version of a 2 (2w3 to be exact), Cher’s your woman.

Also, sorry Twos, both these examples are unhealthy versions of your Enneagram type. You might enjoy finding the Marvel Woman with Your Enneagram Type more.

Enneagram Threes – Stella Payne and Jerry Maguire

Average Enneagram Three Characteristics: Ambitious, Success-Oriented, Image-Conscious, Adaptable, Concerned with Efficiency, Fear of Being Worthless

Stella Payne from How Stella Got Her Groove Back is the quintessence of a successful and ambitious Enneagram Three. She’s a high-powered stockbroker who has dedicated her life to achieving success and recognition in her career. But sometimes she takes on too much and doesn’t give herself a chance to have fun, take a break, and let loose. Everyone in her life realizes this is a problem and pressures her to change. Enter a vacation to Jamaica and the attention of a young, attractive Taye Diggs! Stella’s tendency to “lose herself” in achievements and work is a chronic problem of the average to unhealthy Three. In the end, Stella realizes sometimes she’s got to make mistakes, experiment, and figure out who she really is, not just what she can accomplish.

I’m pretty sure when you saw Jerry Maguire’s name, you also automatically heard “Show me the money!” in your own brain. At least I did. Charismatic and driven, Jerry is a sports agent living on the edge of success and excess. He’s charming, witty, ambitious, and tireless. Like most Threes he can work relentlessly to get his goal and is concerned with the image of success. In fact, he’s so focused on “succeeding” in everything that he winds up losing track of what he really wants and how he really feels. His famous line, “Show me the money,” while initially a call for financial success, ironically becomes a plea for real value and respect in his personal and professional relationships. Like Stella, Jerry’s story is tale of a Three’s evolution from pursuing external validations to seeking genuine self-worth, meaning, and fulfillment.

Find out more about Threes: The Enneagram 3: The Achiever

Enneagram Fours – Tom Hansen and Sam

Average Enneagram Four Characteristics: Introspective, Romantic, Sensitive, Dramatic, Self-Absorbed, Fear of Being Ordinary

Sam from Love, Actually is really the most likeable character in the entire movie. If you don’t like Sam, we have a problem. He’s in love and it’s destroying him. Not making him happy, filling his heart with sunshine and rainbows, it’s making him miserable. If there isn’t anything more Four than that, I don’t know what it is. He’s introspective and consumed by his feelings for Joanna, despite the obstacles in his path. This determination to pursue his heart’s desire, regardless of the practicality or likelihood of success, is one quality of the Enneagram 4 type. Sam’s willingness to put himself in a vulnerable position, go against the norm, and express his emotions is a strength of the Four and can ultimately lead to deep connection and fulfillment.

Tom Hansen from (500) Days of Summer is a textbook example of an average to unhealthy Enneagram Four, particularly in how he navigates the arena of love and relationships. Driven by a deep-seated envy, Tom constantly compares his own romantic experiences to an idealized version of love, one that is often glorified in cultural narratives and societal expectations. His imagination and his feelings drive him. Even when life seems mundane and empty, he hopes that with the discovery of “true love” the missing puzzle of his identity and meaning will be filled. Like many average to unhealthy Fours, Tom believes there’s a lack inside that he can only fill by finding “the one.” Tom’s quest for fulfillment through romantic encounters is anchored in the hope that having what others appear to enjoy will bring him the happiness he craves. Unfortunately, this sets the stage for inevitable disappointment. Real people don’t match idealized visions and imaginations, and Tom grapples with the stark contrast between his romanticized ideas and the messy, imperfect reality of love. In the end, Tom realizes that personal growth and honesty with himself and his worldview is the key to happiness.

Find out more about Fours: The Enneagram 4: The Individualist

Enneagram Fives – Jamie Bennett and Ellie Chu

Average Enneagram Five Characteristics: Analytical, Observant, Private, Intense, Curious, Fear of Incompetence

Jamie Bennett from Love, Actually is probably the sweetest Enneagram Five we’ll see in a romantic comedy. On top of that, he’s one of the only characters in Love, Actually who doesn’t have a pretty messed up romantic fixation. He retreats to a quiet haven in France after a heartbreak, delving into his writing and eschewing all social interactions (minus some shy nods and gestures with his housekeeper, Aurélia.) Jamie’s approach to life is reflective and deeply introspective, preferring the company of his thoughts and a blank page to write on over social interactions. This solitude becomes his workshop for understanding himself and the world around him. When Jamie does discover that he has feelings for Aurélia, in typical Five fashion he attempts to learn her language, Portuguese, first. He won’t even risk attempting to show her he has feelings for her until he can prove his competence in understanding her language.

Ellie Chu from The Half of It has the intellectual, curious nature of the Enneagram Five. Like most Fives, Ellie keeps a wall around her to protect herself from anxiety or potential failure. But when she gets the job of ghost writing love letters on behalf of her thickheaded classmate Paul Munsky, Ellie’s world transforms. They are both in love with the same girl, Aster Flores, but Ellie is not willing to reveal her feelings. She examines love and its complexities first narratively, through writing for Paul, before acting on it in real life. It’s almost as if the intellectual exercise of writing about love frees her from the fear of expressing herself. Like many Fives, Ellie is more comfortable in the world of the mind and imagination rather than the world of action. But as The Half of It progresses, we see her start to take more risks and grow in confidence to pursue her own independent goals.

Discover more about Fives: The Enneagram 5 – The Investigator

Enneagram Sixes – Jack Callaghan and Anna Scott

Average Enneagram Six Characteristics: Loyal, Engaging, Responsible, Anxious, Suspicious, Fear of Being Without Support

While You Were Sleeping is probably my mom’s #1 favorite movie of all time. I can’t think of this movie without remembering childhood evenings, curled up on a blanket on the floor, laughing as Sandra Bullock’s “Lucy” bumbles through one impossible situation after another. Jack Callaghan, the older brother of Peter Callaghan (who’s in a coma for most of the movie,) is a wonderful representation of the Six Enneatype. When he first meets Lucy, the movie’s main character who pretends to be engaged to Peter, Jack is understandably skeptical and suspicious. As an Enneagram Six, he’s naturally cautious and anxious, especially when it comes to his family. Like most Sixes, Jack has the dependability, responsibility, and pragmatism of the Six. He demonstrates this through taking on the family business and stepping up to support everyone while Peter is in a coma. But as the story unfolds, we see Jack’s loyalty and dedication extend beyond just his family, as he starts to fall for Lucy and stands by her when she needs him most.

Anna Scott from Notting Hill showcases another facet of the Enneagram Six personality: the struggle with self-doubt and the longing for a stable, supportive environment. Despite her glamorous life as a famous actress, Anna is inherently anxious and insecure, searching for something real in a world filled with superficiality. Her vulnerability and the rollercoaster of emotions she experiences in her relationship with William Thacker spotlight the Six’s quest for security and fear of abandonment. But even with all her acclaim and fame, Anna still has the grounded nature of the average to healthy Six. After all, who can forget her line “I’m just a girl, standing in front of a boy, asking him to love her.”

Discover more about Sixes: The Enneagram 6 Loyalist

Enneagram Sevens – Vivian Ward and Yas

Average Enneagram Seven Characteristics: Enthusiastic, Fun-loving, Spontaneous, Scattered, Optimistic, Fear of Being Deprived or in Pain

Vivian Ward has not had an easy life; growing up in an abusive home, she’s had to learn to forge her own way and not depend on anyone but herself to survive. But like a typical Seven, she doesn’t let the knocks of life keep her down for long. Her spontaneous and opportunistic nature shines through from the moment she steps into Edward’s car, turning a business transaction into an adventure of a lifetime. While there are definitely some moral problems with Pretty Woman, Vivian’s character is impossible not to love. She brings compassion, lightness, and joy into the lives of others, and encourages Edward to see the world beyond his billion-dollar empire. Despite her circumstances, Vivian remains bright, enthusiastic, and full of dreams for the future.

Yas, from Rye Lane, is a free-spirited Maverick, doing whatever she can to ease her own broken heart, and the heart of her newfound friend, Dom. In typical Seven fashion, Yas is always on the go, constantly chasing new experiences and trying new things. She encourages Dom to take new risks and embrace a spirit of adventure, yet underneath her dynamic, bold exterior is someone who, like many Sevens, has a more vulnerable interior. She just tries to mask this by always seeking out new distractions and excitement. Her fear of being deprived or in pain drives her to avoid facing her inner struggles, constantly keeping herself busy with a million different things.

Find out more about Sevens: The Enneagram 7 Enthusiast

Enneagram Eights – Kat Stratford and Tracy Lord

Average Enneagram Eight Characteristics: Direct, Self-Confident, Decisive, Protective, Confrontational, Fear of Being Controlled or Vulnerable

Kat Stratford from 10 Things I Hate About You was a symbol of edginess and rebellion back when I was 16-years-old. I think every young Thinking-Judging girl (or Feeling-Perceiving girl, for that matter) found in her some sort of kindred spirit. She embodies the fierce independence and resilience of the Enneagram Eight. Fearlessly outspoken and unapologetically herself, Kat refuses to conform to anyone’s expectations. Her confrontational nature sets others on edge, but it also masks a deep-seated vulnerability and a desire to protect those she loves. She was duped once, and it’s NEVER going to happen again. But for Kat, part of her growth lies in learning to let down her defenses and allow herself to be open and vulnerable, which is an important step for growth for all Eights.

Tracy Lord from The Philadelphia Story is another strong Eight character. Like Kat, Tracy refuses to let anyone control or manipulate her. She’s argumentative, direct, confrontational, and magnetic. Unlike many women in her time, Tracy wasn’t afraid to speak her mind. She’s fiery, intense, and runs on instinct. Eights are known for this. They are part of the Body triad and trust their instincts to guide them. They guard their true nature, putting on a tough front (Tracy does the same. When people try to get to know her, she retorts with lines like “Oh, we’re going to talk about me again, are we? Goody.”) But underneath her strong exterior lies a deep fear of being vulnerable and controlled. This fear is what drives her to push people away and maintain control over every aspect of her life.

Read This Next: The Enneagram 8 – The Challenger

Enneagram Nines – William Thacker, Patrick Verona, and Kathleen Kelly

Average Enneagram Nine Characteristics: Peaceful, Receptive, Comforting, Complacent, Optimistic, Fear of Loss and Separation

William Thacker, from Notting Hill, epitomizes the Enneagram Nine’s desire for a peaceful and uncomplicated life. He’s a humble bookstore owner in London with an affable, good-humored personality. Like most Nines, he’s accepting, calm, and unhurried. Despite the whirlwind romance that unfolds, William’s initial resistance to disrupt his tranquil life highlights the Nine’s aversion to conflict and change. However, his character arc demonstrates the growth of a Nine, as he steps out of his comfort zone to pursue love, showing that even the most peace-loving individuals can courageously chase what truly matters to them.

Patrick Verona from 10 Things I Hate About You, at first glance, might not seem like a typical Nine due to his rebellious exterior. However, he’s surprisingly patient, calm, and easy-going once people get to know him. He doesn’t want to bother anyone else, and he doesn’t want to be bothered. While he’s initially presented as a one-note angry outsider, this isn’t his true personality. He and Kat are both outsiders, and while Kat shows others a more bristly, angry, reactive, intense side of herself, Patrick’s aura is more playfully rebellious, charming, and “chill” for lack of a better word. He’s not lashing out at people; he’s doing his own thing, even if that thing means lighting a cigarette with a bunson burner. He hides beneath his rebellious exterior as a way to be left alone and unbothered, not as a way to get back at anyone in particular.

Kathleen Kelly in You’ve Got Mail has that comforting, warm presence that Nines are famous for. Owner of a small, cozy bookstore (maybe bookstore owner is the ideal job for a Nine?), Kathleen creates a welcoming space for her customers and her employees. Throughout the film, her struggles with change and confrontation demonstrates the challenges Nines face when their peaceful existence is threatened. She admits to “freezing up” when the opportunity for a critical comeback presents itself. She struggles to reveal her true feelings; staying in a loveless relationship because maybe it’s more comfortable, or she doesn’t want to deal with a nasty breakup. But as the story progresses, we see her growth, as she learns to stand up for herself and assert her desires.

Find out more about Nines: Seven Struggles of the Enneagram Nine Type

What Are Your Thoughts?

Do you relate to the characters with your Enneagram type? Are you unsure what your Enneatype is? You can take our questionnaire to find out. But let me know if you resonate with these characters or if you have other suggestions! I’d love to hear your thoughts.

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