MTV’s Awkward 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 6, also known as “Don’t Dream it’s Over,” where T tries to win Adam back and Jenna has a stressful dream involving all her ex-boyfriends. Here are the five most awkward moments from this episode of Awkward in chronological order.
1. After the mess that was last week’s engagement party, Jenna and T decide to pop in a Sex and the City DVD and have a girls’ night in. But they soon discover this DVD isn’t actually Sex and the City: it’s the HBO show’s X-rated cousin, Sex in the Titties — and it belongs to Jenna’s dad, which they know because there’s a Post-it note to Lacey from Kevin on the packaging. Some things you just don’t need to know about your parents, most notably their porn tastes.
2. T spontaneously decides to drive to Adam’s base at 11 p.m. and declare her love for him. She’s pumped, and we know this because she straight-up jams out to Donora’s “Take My Heart” on the drive there, one she thinks she’s doing alone until a wasted Gabby pops up from the backseat. Lesson learned: Always check the car for surprise passengers before screaming along to the radio.
3. Jenna is faced to force all her exes in Sex in the City-style (tutu included) dream sequences, which might not be real, but are really, really uncomfortable. On the flipside, though, she does wake from this dream with the realization that she loves Matty and always has. If only all dreams were this helpful.
4. Once T makes it to the base (and once Gabby convinces the guard to bring Adam out by fake-crying), she presents her ex-fiancé with one of her classic mile-a-minute monologues in an effort to get him back. Unfortunately, her attempt is terribly unsuccessful. “Tamara, you took my grandmother’s ring,” Adam tells T after she finally gives him a few seconds to speak. “You are so full of s—.”
5. As No. 4 indicates, T didn’t exactly woo Adam back into her life — but at least she had Gabby and Jake there to hug her afterward. The three share a sweet moment before Jake suggests they get a room, what Gabby and T first assume is him trying to get them to have a threesome. He actually just wants to crash for a bit since they’ve all been up all night, but after the other two playfully scold him, he (jokingly — maybe) proposes they do go forward with a threesome. Teenage boys: so clueless, so hopeful.
Watch Awkward Mondays at 9 p.m. ET on MTV.