7 Best Miles moments from Overcompensating

Prime Video’s new comedy drama, Overcompensating, has quickly become one of the most talked-about shows since its premiere on May 15, 2025. Created by Benito Skinner, Overcompensating narrates the story of Skinner’s character Benny and his friends Carmen (Wally Baram) trying to fit in at their college and also learn to be comfortable in their own skin.

Benny is closeted and tries to find out about his s*xuality after he gets attracted to one of the guys named Miles (Rish Shah) at the university. While Benny initially freaks out and avoids talking to him, even after Miles approaches him a couple of times, the two later become good friends. There are many moments that resulted in Benny developing a crush on Miles due to his behavior toward him. Here’s a list of the 7 best moments of Miles from Overcompensating that make him one of the popular characters of the show.

Disclaimer: This entire article is based on the writer's opinion. Reader discretion is advised.

7 Best Miles moments from Overcompensating

7) The coffee shop scene (Season 1, Episode 2)

The awkward and meet-cute scene of Benny and Miles in the coffee shop is one of the best early scenes of the two in Overcompensating. After meeting in the film introduction class that Benny followed Miles into, where they both lied about their favorite movies being Godfather and Godfather II, they met in the coffee shop.

They both use the names of each other’s favorite films to break the ice and then introduce each other, and they also later decide to meet at the Rockbar club for a party. It appears from the first meeting that Miles wants to become friends with Benny but is afraid of his feelings toward him.

6) Miles hugs Benny (Season 1, Episode 3)

Benito Skinner and Rish Shah in Overcompensating | Image via Amazon MGM Studios

In episode 3 of Overcompensating, after Carmen is taken to the hospital due to the accident with the beer bottles, Benny is alone and eats pot brownies after being forced by Peter. High on the pot brownies, Benny finds Miles at the tailgate event.

While he is high, his fear of being judged by others remains, and a highly emotional and high Benny asks Miles for a hug. Miles doesn’t understand the reason but still gives him a hug, which is a lot for both of them, as Benny has only avoided talking to Miles until then.

5) Miles reveals he hasn’t seen The Godfather (Season 1, Episode 2)

While bringing back Benny’s fake ID, which he had left at the party, in episode 2 of Overcompensating, Miles finds Benny watching The Godfather. Benny admits to him that he hasn’t watched it before, prompting Miles to reveal the same.

Miles then asks Benny about his actual favorite movie, which he reveals to be Megan Fox’s Jennifer’s Body, which coincidentally happens to be Miles' favorite as well. This was one of the early conversations between the two that suggested that they might become good friends.

4) Miles and Benny finish the first task to join the F&G club (Season 1, Episode 4)

The first step toward Miles and Benny’s relationship happens when they are left in the woods for their competition to join the F&G club. In episode 4 of Overcompensating, all the freshmen boys are left in the woods and are required to find their way back to their campus.

While Miles has no idea how to navigate through the woods, Benny helps him as he reveals that he is a Boy Scout. Benny gets over his awkwardness with Miles as they talk, making this one of the most important scenes of Miles and Benny in Overcompensating.

3) Miles pulls Benny out of his imagination about everybody judging him (Season 1, Episode 3)

Benito Skinner and Rish Shah in Overcompensating | Image via Instagram: overcompensating

In the Overcompensating episode 3, Benny gets nervous as he goes out to have lunch alone. He begins thinking that everyone was looking at him and judging him for eating out alone. This fear of Benny keeps on alarming him through the series as he is still closeted and fears someone outing him.

While he imagines everything bad, Miles comes and sits with him, pulling him out of his imagination. Although he unintentionally helps Benny, who still leaves Miles alone due to his own feelings, leaving Miles feeling the same way about being judged by the whole cafeteria.

2) Miles takes care of Benny (Season 1, Episode 4)

Rish Shah in Overcompensating | Image via Instagram: rishshah

Being a part of the F&G club was not as easy as finding their way back to campus from the woods. The boys find out about this later when they are ordered to eat raw fish in episode 4 of Overcompensating.

Since Miles is a vegetarian, Benny helps with the raw fish eating challenge. However, it doesn’t go well for him as he gets sick. After they attend the Charlie XCX concert, Miles helps Benny up, takes him to his dorm room, and takes care of him. Miles is grateful to Benny as he helped him out during the competition, and so he wants to make sure Benny is ok, which makes Benny’s feelings for him stronger.

1) Miles tries to talk to Benny (Season 1, Episode 5)

Episode 5 is regarded as the most crucial episode of Overcompensating, as Benny finds out that Miles is interested in girls. In the subsequent episodes, Miles tries to talk to Benny several times, but Benny turns him down every time. However, Miles doesn’t give up as he even talks to Carmen to know how to talk to Benny.

While Miles’ s*xuality is not revealed in this season of Overcompensating, Benny assumes him to be straight and begins avoiding him. Miles, still unaware, tries his best to talk to his friend even if he refuses to talk to him.