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lives up to its name — and each week, EW will chronicle the comedy-drama’s most uncomfortable moments. This time, we’re looking at season 5, episode 8, also known as “An Indecent Promposal,” where everyone struggles with the politics of prom season. Here are the five most awkward moments from this episode of

1. Someone wants to go to prom with Cole! Except Cole ruins the moment by riffing on how lame prom is with Teo, who for some reason is with the once-happy couple when the asking goes down. Cole fixes the situation later by asking the guy to prom with a latte, but the weirdness of Cole and Teo’s playful-but-mean-spirited banter lingers on.

when Jake asks Gabby to prom by serenading her with an original song in the library. He’s confident; she’s overjoyed — but there’s no arguing that a guy walking over tables with a guitar in hand and crooning for a girl to “say yes” isn’t unbearably cheesy.

3. Post-serenade, Jake tells Gabby he’s decided to take a gap year between high school and college. She’s shocked and responds by giving him some options for ways to spend his time during that year. Jake tells her that he already has a plan: He’s going to live with his mom and his sister and make money waiting tables, an idea Gabby admits is “embarrassing.”

embarrassing. Have fun being a snob at Stanford, Gabby!)

4. Sergio is finally fed up with Sadie always making everything about her, and he tries to tell her this by saying it’s always something with her. For example, he says, “tomorrow it’s going to be about the New York subway,” (reminder: Sadie’s going to Columbia University) which Sadie replies to by saying, “I won’t take the subway!” with her characteristic as-if tone. It’s not surprising then that this “conversation” ends with Sergio officially breaking it off with her.

5. Jenna tries to back away from Matty all episode, but it comes to a head when Lyssa forces the two to slow dance together during prom rehearsal. Jenna tries to get out of dancing with him — she’s too attracted to him and so being around him is painful — but Lyssa forces the two together, causing Matty to confront Jenna about how he thinks she hates him now before he eventually storms out. If only you knew, Matty: Jenna far from hates you.

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