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That Awkward Moment (2014) Plot Summary & Timeline

That Awkward Moment (2014) movie poster

That Awkward Moment is a 2014 comedy and romance film directed by Tom Gormican, running 1 hour 34 minutes. This page retells the whole story in 642 words (about 3 minutes to read) and covers 13 key events in order, 4 characters, where and when it is set and 2 themes. Looking for the cast, ratings and where to stream it? See the movie page for That Awkward Moment.

to read the plot summary
3 min
key events in the timeline
13
characters profiled
4
themes explained
2
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That Awkward Moment (2014) movie poster
Released
Runtime
1h 34m
Director
Tom Gormican
Genres
Comedy, Romance
Original language
English
No spoilers

What Is That Awkward Moment About?

The premise of That Awkward Moment in 360 words, with nothing given away. The full story follows below.

In the bustling rhythm of New York City, three close‑knit friends drift through their thirties with a shared love for spontaneity and a penchant for avoiding anything that feels too permanent. Jason works at a publishing house, juggling design deadlines with a carefree charm, while his best friend Daniel balances his own creative pursuits with a laid‑back outlook that mirrors Jason’s. Their world is a mix of coffee‑shop chatter, downtown bars, and the endless possibilities that a city that never sleeps seems to offer.

When their longtime companion Mikey announces that his marriage is unraveling, the trio is forced to confront the idea that commitment—whether to a career, a friendship, or a romance—might be inevitable. In response, they make a lighthearted yet earnest pact to remain “commitment‑free,” a promise that feels both rebellious and comforting against the backdrop of a city where everyone seems to be searching for something deeper. This agreement becomes a quiet framework for their interactions, shaping the way they talk about love, loyalty, and personal growth.

Even as they cling to their pact, each man begins to notice sparks beyond their usual circle. Ellie appears as a captivating presence in one of Jason’s urban haunts, her wit and intelligence hinting at a connection that could challenge his resolve. At the same time, Daniel finds himself drawn to the sophisticated Chelsea—a friend whose confidence and allure suggest possibilities that extend beyond casual banter. Meanwhile, Mikey’s own lingering feelings for his estranged partner Vera linger in the background, adding an undercurrent of unanswered questions. The film’s tone balances clever comedy with genuine heart, letting the awkward moments and unspoken tensions linger just long enough to keep the audience curious about where these tentative bonds might lead.

Set against a cityscape that feels both intimate and expansive, the story explores the delicate dance between friendship and romance, the fear of losing one’s freedom, and the unexpected ways life nudges us toward intimacy. With witty dialogue, relatable anxieties, and a light‑hearted yet sincere atmosphere, the characters hover on the edge of change, inviting viewers to wonder whether their commitment‑free promise will hold up when love quietly knocks on their doors.

Full plot

What Happens in That Awkward Moment?

The complete story of That Awkward Moment, from the first scene to the last, in 642 words (about 3 minutes). Spoilers throughout.

Spoilers ahead

As Jason settles onto a bench in New York City, his reflective voiceover transports viewers back to the roots of his situation. He shares his realization that every romantic relationship eventually hits a turning point – that moment when one partner yearns for greater commitment. For Jason, this is often the harbinger of the end for any potential romance. This insight arises from his desire to hold on to the thrill of casual encounters, which he has come to cherish.

Moving ahead, we find Jason in his routine at a publishing house, working alongside his dependable friend Daniel on book cover designs. They are joined by their colleague Mikey, a former doctor now navigating life as a husband after receiving an unexpected divorce request from his college sweetheart, Vera. To commemorate this significant shift in Mikey’s life, the group heads to a local bar to celebrate his newfound freedom.

As they socialize, Daniel’s glamorous friend Chelsea attempts to distract Mikey from his marital woes. It is during this outing that Mikey meets “Glasses,” while Jason finds himself drawn to Ellie, connecting instantly after amusingly sabotaging another suitor vying for her affection. Though Mikey finds a promising lead with Glasses, he hesitates to take the next step, focusing instead on unraveling his complicated situation with Vera.

Jason’s chemistry with Ellie intensifies, leading him to take a leap forward – only to awkwardly retreat from her apartment after misinterpreting the circumstances, mistakenly believing she is a sex worker. As time goes by, Jason and Daniel traverse the intricate landscape of romance, embarking on distinct journeys with Ellie and Chelsea respectively. The tension runs high as they tiptoe around their earlier agreement to remain unattached, shrouding their relationships in secrecy. Meanwhile, Mikey rekindles his desire for Vera, culminating in a passionate encounter at the hospital that reignites the flames of their romance.

As Thanksgiving nears, the dynamics among the friends become increasingly fraught. Jason grapples with the decision of whether to honor Ellie’s invitation to her father’s funeral while wrestling with his reluctance to commit fully. Mikey’s dinner with Vera turns introspective, prompting her to confront a painful truth: her feelings have waned. Daniel finds himself caught in the turmoil of his evolving emotions for Chelsea.

The holiday meal soon transforms into a confrontation stage where buried secrets resurface and bonds weaken. Ultimately, Jason opts out of attending the funeral, leading to a strain in his relationship with Ellie. Mikey’s interaction with Vera acts as a wake-up call, pushing him to recognize the reality of their situation. Daniel’s underhanded actions come to light, leaving his connection with Chelsea in disarray.

In the aftermath, the friends must grapple with the consequences of their actions. Mikey reaches out to “Glasses” to explore a new romantic avenue, while Daniel crosses paths with Chelsea once more, potentially mending their bond. However, Jason finds himself in a stasis, yearning for Ellie, who is now absent from his life.

Fast forward two months, and Mikey and Daniel join forces to help Jason navigate his path back to Ellie’s heart. They motivate him to seize the moment during her book readings, hoping to rekindle their romance. Nevertheless, fate intervenes, and a crowded reading room leaves Jason feeling perplexed. Undeterred by the odds, he dares to improvise a heartfelt reading that intertwines their shared journey and concludes with a fervent request for a fresh start in Gramercy Park.

As the story circles back to the beginning, we find Jason waiting patiently in Gramercy Park, anticipating Ellie’s arrival. Time seems to stretch as the serene ambiance envelopes him, each passing hour marked by the quiet lapping of leaves. Finally, Ellie takes her place beside him on the bench, and he breaks the silence with a casual “So…”, opening the door to a potentially enlightening conversation that may unravel the complexities of their intertwined lives.

Timeline

That Awkward Moment Timeline: Every Key Event in Order

13 key events in the order they happen, from “Jason's Reflection” to “A New Beginning”. 7 events name a place, across 5 locations.

  1. 1

    Jason's Reflection

    In New York City, Jason reflects on his romantic experiences and the inevitable turning points in relationships. He realizes that the desire for greater commitment often signals the decline of casual encounters, which he values.

    Where:New York City

  2. 2

    Work at the Publishing House

    Jason is shown at his job in a publishing house where he collaborates with his friend Daniel on book cover designs. They also work with their colleague Mikey, who is struggling with a recent divorce request from his college sweetheart, Vera.

  3. 3

    Celebration at the Bar

    To celebrate Mikey's unexpected new phase of life post-divorce, the friends gather at a local bar. This outing becomes a pivotal moment as they seek to support each other and distract Mikey from his heartbreak.

    Where:Local Bar

  4. 4

    Meeting Ellie

    At the bar, Jason meets Ellie and experiences an immediate connection. He comically sabotages another suitor, showcasing his playful side and signaling the beginning of a deeper relationship with her.

    Where:Local Bar

  5. 5

    Mikey's Hesitation

    Despite meeting someone new, Mikey continues to grapple with his feelings for Vera, missing a chance at moving on. His focus remains on resolving the complexities of their past relationship rather than pursuing Glasses.

  6. 6

    Awkward Retreat

    As Jason's bond with Ellie deepens, he makes an awkward exit from her apartment after misjudging the situation. He mistakenly believes Ellie is a sex worker, causing a rift before their relationship can truly blossom.

    Where:Ellie's Apartment

  7. 7

    Emotional Conflicts

    As Thanksgiving approaches, tensions rise among the friends as they each navigate their feelings. Jason contemplates attending Ellie's father's funeral, while Mikey's dinner with Vera forces him to confront the reality of their dwindling relationship.

    When:Thanksgiving

  8. 8

    Confrontation at Thanksgiving Dinner

    The holiday meal becomes a battleground of unresolved feelings, where Jason's absence from the funeral strains his connection with Ellie. Mikey realizes Vera's feelings have diminished, and Daniel faces the consequences of his actions regarding Chelsea.

    When:Thanksgiving

  9. 9

    Aftermath of the Confrontation

    The fallout from Thanksgiving leads to significant changes in the friends' dynamics. Mikey reaches out to Glasses, while Daniel tries to reconnect with Chelsea; however, Jason finds himself stuck, longing for Ellie, who is now distant.

  10. 10

    Support from Friends

    Two months later, Mikey and Daniel team up to help Jason reclaim his connection with Ellie. They encourage him to attend her book readings, where they hope he can express his true feelings and initiate a fresh start.

Show the other 3 events of That Awkward Moment
  1. 11

    Heartfelt Reading

    During one of Ellie's readings, Jason seizes an opportune moment to share a heartfelt reading that intertwines their journey together. This bold move is intended to rekindle their romance and signify his willingness to commit.

    Where:Reading Room

  2. 12

    Waiting in Gramercy Park

    As the story comes full circle, Jason waits in Gramercy Park, filled with anticipation for Ellie's arrival. The tranquility of the park surrounds him as he reflects on the journey that led him to this moment.

    Where:Gramercy Park

  3. 13

    A New Beginning

    Finally, Ellie joins Jason on the bench, marking a pivotal moment in their relationship. Jason breaks the silence with a casual remark, opening the door for a potentially transformative conversation about their future together.

    Where:Gramercy Park

Characters

Who Are the Main Characters in That Awkward Moment?

4 characters, among them Jason (Michael B. Jordan), Daniel (Miles Teller) and Mikey: who each one is and the part they play in the story. 2 of them link to the actor’s page.

  • Michael B. Jordan as Jason (Michael B. Jordan) in That Awkward Moment

    Jason (Michael B. Jordan)

    Played by Michael B. Jordan

    Jason portrays a complex individual grappling with his fears of commitment, often retreating from deeper connections in favor of casual encounters. His journey reflects a struggle to balance the thrill of romance with the desire for something more meaningful. As he navigates his relationship with Ellie, his character evolves, revealing a deeper longing for love.

    • 💔 Heartbreak
    • 🏃‍♂️ Commitment Issues
  • Miles Teller as Daniel (Miles Teller) in That Awkward Moment

    Daniel (Miles Teller)

    Played by Miles Teller

    As a dependable friend, Daniel provides comic relief and insight into the romantic struggles of his companions. He grapples with his own feelings for Chelsea while attempting to support Jason and Mikey. His character reflects the challenges of maintaining friendships against the backdrop of evolving romantic relationships.

    • 👫 Friendship
    • 🎭 Complexity
  • M

    Mikey

    Mikey is a character in transition, navigating life after an unexpected divorce. His emotional journey reveals the struggles of balancing past love with the potential for new connections. Through his experiences, he learns about acceptance and the pursuit of happiness, adding depth to the narrative's exploration of relationships.

    • 🔄 Change
    • 💔 Heartbreak
  • E

    Ellie

    Ellie serves as the romantic interest of Jason, representing his ideal connection amidst his fears of commitment. Her character embodies strength and vulnerability, challenging Jason to confront his emotions. Through their interactions, Ellie becomes a catalyst for Jason's growth, prompting him to rethink his approach to love.

    • 💫 Romantic Interest
    • 🦋 Growth
Setting

Where and When Is That Awkward Moment Set?

That Awkward Moment is set in New York City and Gramercy Park (Modern Day). Here is why the time and place matter to the story.

When

Modern Day

The events of the film unfold in a contemporary setting, reflecting the complexities of modern romantic relationships. This time period showcases the challenges of commitment and connection in an era characterized by casual dating and shifting social norms. As friends navigate their romantic entanglements, the story captures the essence of love and heartache in the present day.

Where

New York City, Gramercy Park

New York City serves as the vibrant backdrop of the film, known for its bustling streets, diverse culture, and dynamic relationships. Among its many green spaces, Gramercy Park stands out as a serene oasis, offering a quiet escape from the city's hustle and bustle. The park is famous for its exclusivity and lush landscaping, making it the perfect setting for pivotal moments in Jason and Ellie's relationship.

  • 🏙️ City
  • 🌳 Park
Themes

What Are the Themes of That Awkward Moment?

2 ideas the story keeps returning to, among them Love & Commitment and Friendship.

  1. 01

    Love & Commitment

    The film explores the theme of love and commitment, particularly the struggles individuals face when transitioning from casual relationships to deeper connections. Characters grapple with their desires for intimacy while fearing the vulnerability that comes with commitment. This tension ultimately shapes their encounters, leading to moments of both growth and heartache.

  2. 02

    Friendship

    Friendship plays a crucial role in the narrative, serving as a support system for the characters in their romantic pursuits. The camaraderie between Jason, Daniel, and Mikey showcases how friends navigate life's challenges together, even as they face their own relationship dilemmas. Through shared experiences, they ultimately learn about loyalty, trust, and the complexities of love.

Tone & mood

What Kind of Film Is That Awkward Moment?

Light in tone, with steady pacing and a straightforward story, going by the plot summary.

Tone
Light
Pacing
Steady
Story
Straightforward
Intensity
Medium
Ending
Happy

A witty and fast-paced romantic comedy about three friends navigating the awkwardness of modern dating in New York City, blending humor with heartfelt moments about loyalty and love.

  • awkward
  • witty
  • bromantic
  • flirtatious
  • mischievous
  • hopeful
  • bachelor lifestyle
  • friendship pact
  • fear of commitment
  • secret relationships

Content notes: sexual content, nudity.

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6 films close to That Awkward Moment in story and themes that have a full plot summary here: Friends with Benefits (2011) and Date and Switch (2014) lead.

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FAQ

That Awkward Moment Plot Questions

5 quick answers about That Awkward Moment, taken from the plot summary, character guide and setting on this page and the film’s credits.

What is That Awkward Moment about?

In the bustling rhythm of New York City, three close‑knit friends drift through their thirties with a shared love for spontaneity and a penchant for avoiding anything that feels too permanent.

Read the full plot summary

When and where does That Awkward Moment take place?

That Awkward Moment is set in New York City and Gramercy Park (Modern Day). The events of the film unfold in a contemporary setting, reflecting the complexities of modern romantic relationships.

The setting explained

Who are the main characters in That Awkward Moment?

The story follows Jason (Michael B. Jordan) (played by Michael B. Jordan), Daniel (Miles Teller) (played by Miles Teller), Mikey and Ellie.

All the characters

What are the main themes of That Awkward Moment?

The summary picks out 2 themes: Love & Commitment and Friendship.

The themes explained

Who directed That Awkward Moment?

That Awkward Moment (2014) was directed by Tom Gormican and runs 1 hour 34 minutes.

Tom Gormican’s films

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