What to read, watch, and listen to if you lovedThat Awkward Moment
Tom Gormican · Film · 2014
If you loved That Awkward Moment, start with Insecure (Issa Rae, 2016) — a series on the same thread. Below: 4 books, 4 series and 2 podcasts, each matched to That Awkward Moment across media.
If you enjoyed the messy, high-stakes navigation of modern dating and friendship in That Awkward Moment, these picks will resonate.
Books on the same thread
Something Borrowed
Emily Giffin · Book · 2005
Shares a thread with That Awkward Moment: Coming of Age.
Much like the secret relationships central to That Awkward Moment, this story explores the complicated moral dilemmas and fallout that occur when close friendships collide with romantic entanglements.
The Third Wheel (Diary of a Wimpy Kid, Book 7)
Jeff Kinney · Book · 2012
Shares a thread with That Awkward Moment: Coming of Age.
The desperate, often clumsy maneuvering to avoid being the odd man out mirrors the frantic energy of the pact made by the protagonists in That Awkward Moment.
Modern Romance
Aziz Ansari, Eric Klinenberg · Book · 2016
Explores: Digital dating culture, Paradox of choice, Sociology of relationships.
This deep dive into modern mating rituals provides the sociological context for the same confusing, commitment-phobic landscape that Jason and Daniel struggle through in That Awkward Moment.
Three Men in a Boat
Jerome Klapka Jerome · Book · 2010
Explores: Friendship, Leisure, British Culture.
The camaraderie of these three men on their journey mirrors the core male bonding dynamic that keeps the characters tethered together throughout That Awkward Moment.
Series on the same thread
Friends
Marta Kauffman · Series · 1994
Shares a thread with That Awkward Moment: Coming of Age.
The reliance on a close-knit circle of friends to navigate the pressures of adult life in the city perfectly echoes the support system found in That Awkward Moment.
Insecure
Issa Rae · Series · 2016
Explores: Black female friendship, modern dating, career struggles.
The racy tribulations and awkward experiences of the protagonist mirror the chaotic, often messy path to maturity that the main characters face in That Awkward Moment.
How I Met Your Mother
Carter Bays · Series · 2005
Shares 2 threads with That Awkward Moment: Coming of Age, Romantic Comedy.
The nostalgic, flashback-driven focus on the evolution of a close group of friends mirrors the coming-of-age journey experienced by the male leads in That Awkward Moment.
The Office
Greg Daniels · Series · 2005
Explores: Office life, Everyday life, Eccentric characters.
The focus on the cringeworthy interactions and eccentric personalities of everyday life captures the same comedic tone of social blunders found throughout That Awkward Moment.
Podcasts on the same thread
Conan O’Brien Needs A Friend
Team Coco & Earwolf · Podcast · 2026
Explores: parasocial relationships, professional intimacy, self-deprecating humor.
The humorous, self-deprecating exploration of professional intimacy and the search for authentic connection reflects the underlying tension between loneliness and friendship seen in That Awkward Moment.
The Secret Patreon
Podcast
Explores: Male Friendship, Improv Comedy, Current Events Commentary.
The focus on unfiltered male friendship and conversational humor provides a similar dynamic to the banter shared between the friends in That Awkward Moment.
Keep exploring
Common questions
Is That Awkward Moment about a group of friends?
Yes, That Awkward Moment follows three best pals named Jason, Daniel, and Mikey. After Mikey goes through a divorce, the trio forms a pact to remain single and avoid commitment while navigating their casual dating lives in the city.
What is the main conflict in That Awkward Moment?
The central conflict in That Awkward Moment arises when the three friends accidentally fall into serious relationships. Despite their initial pact to stay unattached and carefree, they find themselves forced to hide their new romances from one another to maintain their agreement.
Why do the characters in That Awkward Moment make a pact?
The characters in That Awkward Moment make a pact to avoid commitment and remain single after their friend Mikey experiences the end of his marriage. They decide to focus on having fun and enjoying their carefree, unattached lives together as a group.
How does the plot of That Awkward Moment begin?
That Awkward Moment begins with Jason and Daniel enjoying their lives as unattached men. The dynamic changes when they welcome their friend Mikey back into their circle following the collapse of his marriage, leading them to collectively agree to avoid serious relationships.