The most awkward Awkward moments from 'Digging Deep' 

Jenna and Luke get serious in exclusive 'Awkward' trailer

EW chronicles the comedy-drama’s most uncomfortable moments. This time, we’re looking at season 5, episode 18, also known as “Digging Deep,

— but with some harsh consequences. Here are the five most awkward moments from this episode of

1. The only thing worse than a run-of-the-mill hangover is a hangover spiked with the guilt of getting your best friend fired from his job. This is the punishment Jenna, Matty, Tamara, Luke, and Sully get the morning after their ill-advised Fourth of July adventures on the golf course, but somehow, the raging headaches and stomach-turning nausea aren’t enough to dissaude them from having

drinking session that same night — this time, though, they have a mission: Win Jake back by getting him drunk. (Spoiler: It works.)

2. After spending some time apart, Sadie and Sergio have some new, uh, bedroom skills. At first, this creates a rift between the two because it reminds them that they

been with other people in the recent past, and Sadie being Sadie asks Sergio to list everyone he slept with in between. They eventually kiss and make up though — literally.

3. Good news: Jenna finally wrote a piece for Ideabin that made it on the homepage. Bad news: Ethan changed the title of the piece — which is all about Matty — from “From Lovers to Friends to Lovers to Friends (For Real This Time)” to the less civil “Your Needy High School Boyfriend is a LOSER. Dump Him Already.” Isn’t clickbait fun?

4. Jake gets his country club job back, something he’s happy about. Lissa? Not so much. She tells him she expected it was going to be temporary and that what he wants doesn’t line up with what she wants. To recap, Jake’s been fired (because of his drunk friends, no less), re-hired, and dumped in a period of 24 hours.

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5. Despite working for the internet, Jenna doesn’t understand how it works and thinks that just because Matty admittedly doesn’t read Ideabin that he won’t find out about her article. Everybody

reads it though, and Matty suddenly gets an influx of tweets and texts asking him about the story. He’s understandably pissed, even when Jenna points out that she changed his name in the story (to Marc, though — not too sneaky, Jenna). Looks like Matty and Jenna’s short-lived friendship just sunk.

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