When Is Overcompensating?

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In traditional stories, knights might stumble upon a village where an enchantment has been placed to cater to the whims of one fortunate resident. At first glance, everything appears normal, but upon closer inspection, discrepancies arise. Either everyone is unusually joyful or the seasons are mismatched, signaling that someone within the town is manipulating reality unknowingly. This sensation is similar to watching A24’s college comedy on Amazon Prime Video titled “Overcompensating.” Despite its appealing nature and strong writing, the show seems set in a distorted reality, blending elements of 2015, 2025, and everything in between all at once. Several times during my viewing of “Overcompensating,” I had to pause the screeners and attempt to determine the time period in which the series was set. Was it the present? A nostalgic look back at the college years of the main actors, most of whom are millennials? Somewhere in between? Even when special guest star and executive producer Charli XCX appears onscreen, it’s unclear how famous she is. I consulted my colleagues about this, but they were equally puzzled. I searched for press releases and plot summaries for answers, but found none.

The show is designed to be relatable due to its focus on comedian Benito Skinner, aged 31, who grew up as a secretly gay football star in Idaho. He openly discussed his college years filled with parties at straight men’s homes and encounters in fratty bathrooms adorned with posters of popular celebrities like Megan Fox and Kate Upton. The show mirrors Skinner’s life experiences, creating a character named Benny, also from Idaho, who shares the same obsession with Megan Fox, as evidenced by a poster in his dorm room and fantasized conversations. However, unlike Michael Bay, Benny is more of a fan of Jennifer’s Body (2009) and other pop culture icons such as Brendan Fraser from George of the Jungle (1997), Lucky-era Britney Spears, and Glee. These preferences suggest a millennial upbringing that aligns with Skinner’s assumed experiences at age 18. Additionally, when Benny gets drunk at karaoke, he reveals his true feelings by singing Nicki Minaj’s “Super Bass,” released in 2010 and promoted as a single in early 2011. Therefore, it can be deduced that the show is set around 2011, providing a slightly nostalgic atmosphere, reminiscent of the style seen in Lady Bird.

The show, although set in a fictional university called Yates, does not shy away from incorporating contemporary elements such as modern phone interfaces, references to recent technology like Spotify Wrapped, and even mentioning popular chefs like Alison Roman. However, some of these elements seem anachronistic when you consider their actual timelines. For instance, Alison Roman’s fame didn’t skyrocket until mid-2018, yet a character in the show seems to be aware of her by name earlier than that. Similarly, while toxic masculinity is a persistent issue, the humor about frat culture appears to respond to current discussions on inclusion, suggesting references to modern dialogues about sensitivity and welcoming attitudes towards new members.

In the series “Overcompensating,” DiMarco’s character’s girlfriend, portrayed by Mary Beth Barone, who is a friend of Skinner in real life, appears as a cool blonde but secretly adores the Twilight saga. While trying to reconnect with an ex-friend who has become a lesbian, she casually mentions Kristen Stewart, which prompts several queer girls in the background to simultaneously stand up, reminiscent of dogs reacting to a high-pitched noise. This joke is amusing, but it also marks the breakdown of the “Overcompensating” continuum: The storyline requires accepting that someone who was a teenage fan of Twilight (released between 2008 and 2012) is now interacting with queer women who idolize Stewart as an openly gay icon (since 2017), all while being the same age (18-22).

Indeed, it’s plausible that some queer women were aware of Stewart’s sexuality before she publicly came out or simply admired her aura. It could be possible that Malone’s character got into Twilight movies late and those girls got into Stewart early. However, the mental gymnastics required to believe this storyline are considerable, and I often find myself questioning whether any characters in Overcompensating have ever seen the 2016 film Certain Women or were early admirers of Lily Gladstone.

Performing acrobatics with Charli XCX, the pop star and executive producer of “Overcompensating”, is far more tiring compared to other acts. Charli, aged 32, is a friend of Skinner’s and is responsible for most of the show’s music selections. In one episode, she appears as herself, expressing her dislike for performing her hit song “Boom Clap”, which was released in 2014. This contradicts the idea that “Overcompensating” is a period piece depicting millennial life, since Charli would be several years past the release of that song.

Interestingly, the show doesn’t fully transport Charli into the present. At her concert, she doesn’t perform any songs from “Brat”, but rather “I Love It” (which became popular due to its inclusion in “Girls” in 2014), “Boys” (released in 2017), and “Boom Clap”. This setlist seems to hark back to when Charli was touring with Taylor Swift around 2018. You can also hear a faint echo of “Girls Night Out”, released in 2018, as a kind of hidden reference. However, would a sorority girl from that year be so enamored with Charli as to attempt drug theft for her? Charli has been a favorite among pop fans for years before “Brat”. Is it significant that a gay man might be obsessed with her? Yes, perhaps, given the nature of Charli’s fandom. But then, what does this imply about the straight love interest? And how do we reconcile “Party 4 U” (released in 2020, re-released in 2025) playing during the end credits?

The inconsistency in the show can be dismissed by acknowledging that high-school and college TV shows have traditionally portrayed teenagers as if they were older individuals. Shows like Riverdale, Buffy, and even those from the era of Aaron Spelling, such as Greek, have followed this pattern. However, what makes Overcompensating unique is that it explores pop culture alongside its portrayal of queer identity. The character Benny, for instance, represents a young man grappling with conflicting societal messages about his identity. He’s presented as an overachiever, influenced by both the traditional masculine fraternity culture, which encourages repression, and his fascination with more progressive music and films, which promote self-expression.

In simpler terms, you could say that on Overcompensating, the show’s exploration of pop culture is closely tied to its portrayal of a character coming to terms with his queer identity. Benny, who is an overachiever, struggles with conflicting messages about how he should live in society from both traditional masculine groups and more progressive influences.

The show “Overcompensating” portrays a character named Benny who struggles with his identity as a queer individual in a world where others have had relatively easy coming-out experiences (represented by the character Owen Thiele, who serves as a mentor figure). Benny has built up a tough-guy image for himself and takes advantage of a girl he pretends to date for popularity. The show delicately handles this complex dynamic while incorporating humor reminiscent of “American Pie.” However, the ambiguity about the time period creates tension since a character’s closet experience is heavily influenced by the culture they’re immersed in. This means that characters from different eras, like the college kid hiding his love for Nicki Minaj and “Glee” during the second Obama term versus today’s college student embracing Charli among the zoomers, would have distinct experiences due to the differing social climates at those times. It is unclear exactly which time period this show is set in, as both scenarios are possible and intriguing. The characters in each scenario are unique and interesting but navigate different socially-encoded programming.

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2025-05-16 01:54