‘Gossip Girl’ Premiere: 14 Hottest Hookups From the Series’ Past 5 Seasons (GALLERY)

Lauren DiMascio / October 8, 2012

Gossip Girl Showdown
See who has the better style: Blake as Serena or Leighton as Blair.
'Gossip' Guy: Barry Watson
Serena gets a love interest on The CW show.
It’s the beginning of the end for The CW’s Gossip Girl as Monday marks the season premiere of the sixth and final season.

When we last left off, our favorite Upper East Sider Serena (Blake Lively) was passed out on a train out of town after being told to get out of both Blair (Leighton Meester) and Dan’s (Penn Badgley) lives.

Meanwhile, Blair made her final decision to be with Chuck (Ed Westwick) and the heartbroken Lonely Boy went to Rome with Georgina (Michelle Trachtenberg) to write another tell-all book about his friends.

As for the adults, Lily (Kelly Rutherford) picked Bart Bass (Robert John Burke) over the love of her life Rufus (Matthew Settle).

To prepare you for the final season of this epic series, Celebuzz is taking a look back at some of our favorite and most scandalous hookups through the years.

And if you think the hookups thus far have been good, just wait until you see Season 6…

Our friends on the Upper East Side have been somewhat of an incestuous group these past five years: Both Dan and Nate have hooked up with “frenemies” Blair and Serena, while Blair alone has been with everyone from the Prince to Monaco to the love of her life, Chuck Bass.

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However, ladykiller Chuck has had his fair share of the ladies all over the city of Manhattan too.

Season 6 seems par for the course of more delicious drama as the first two episodes show us not one, not two, but three new relationships on the Upper East Side. We can’t tell you much about who’s kissing whom, but let’s just say at least one of them will make you say, “OMG!”

The sixth and final season of Gossip Girlpremieres Monday at 9 PM on The CW.

Who do you think will end up together in the end? See the show’s hottest hookups in our gallery above, then sound off in the comments below.