Blake Lively as Serena Van Der Woodsen

Gossip Girl – Season 4 Blake Lively as Serena Van Der Woodsen and Ethan Peck

Sadly, we’ll be hearing “XOXO, Gossip Girl” for the last time this year. Five seasons in, and there have been tears, deaths, broken hearts and a mountain of handbags. The show brought you OMFG television – I’ve never quite been able to erase those mind-blowingly inappropriate posters from my mind. As Gossip Girls’ stellar (and glamorous!) reign comes to a close, let’s look at the best episodes from each season — good enough to re-watch.

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Season 1, Episode 1 “Pilot” — The pilot kick-started the New York based series and centered around the mysterious Serena van der Woodsen returning to Manhattan. Witty Chuck Bass and young Jenny Humphrey’s most memorable interaction (and a scary one at that) occurs at the Kiss on the Lips party. After many years and seasons, these socialites have come a long, long way from high school parties and debauchery…or maybe not.

Season 2, Episode 13 “O Brother, Where Bart Thou” — Chuck Bass reveals his humanity. This penultimate episode changes his character forever and shakes up his relationship with Blair Waldorf. Beware: Sit next to a box of tissues when re-watching and avoid runny mascara.

Season 3, Episode 15 “The Sixteen Year Old Virgin” — Jenny Humphrey is pressured to lose her virginity by Damien, a much older drug dealer. Is she ready to take the next step? Regardless of whether you’re Team Jenny, her storyline becomes a familiar one. The pressure to be older like Damien, like her brother, like all the people around her, comes to a head, and she must make a harrowing decision: am I ready or not.

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Season 4, Episode 2 “Double Identity” — While in Paris, Blair Waldorf confronts Chuck in this beautifully directed episode. Their relationship status is questioned.  Even if the events don’t unfold the way you hope, the moment they share together is worth pressing play. The episode also uses Sia’s “I’m in Here” so perfectly that you’ll most definitely need to replenish those tissues.

Season 5, Episode 24 “Return of the Ring” — The fifth season finale gives us (a little) closure in the Blair and Chuck love saga. Will they be together or will they separate? Re-watch to remember.

The final season of Gossip Girl premieres Monday, October 8th at 9pm. Apply some red lipstick in homage to the show or use it to mark your calendars because the end is near. And Gossip Girl has left a lengthy clothes trail all along the way.

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– Becca Ritchie