Spotted: The Top Ten O-M-G Pairing On The Upper East Side!

Pregnancies! Prisoners! Princes! Just when you thought everyone on Gossip Girl was done swapping partners, here’s a list of this year’s most perfect (and pathetic) pairings.

-Kimberly Lamontagne

Chuck Bass & Raina Thorpe

Mr. Bass found his female equivalent in Raina. Equally skilled in the business world and the bedroom, Raina came back to Manhattan with her daddy; a former associate of Chuck’s father. Long story short Raina said bye-bye as Bass proved once again to have his priorities in disarray.

Nate Archibald & Raina Thorpe

It wouldn’t be the first time Nate and Chuck pursued the same woman. After Chuck and Raina break up, Chuck enlists the help of Nate to help win Raina back, but the plan backfires when a flame ignites between Raina and Nate. After a crazy hostage situation involving Blair and Raina’s father, Raina says ciao to N and heads back to Chicago.

Serena van der Woodsen & Ben Donovan

Who doesn’t love a good ol’ jail bird, right? If John Waters’ 1990 classic Cry-Baby taught us anything, it’s that. Serena sure has had her run of gentlemen callers, but the prisoner boyfriend was a new low. To be fair, he was wrongly accused. And, it was kind of Serena’s mom’s fault he was locked up to begin with. Okay, so he wasn’t the worse guy in the world, but Dan was so obviously crushed by Serena and her convict love interest. GG Flashback: Ben a.k.a. Professor Donovan was an English teacher at Serena’s boarding school, which is where she developed an appreciation for him.

Blouis: Blair Waldorf & Prince Louis Grimaldi

Prince, or not, his royal highness, Louis needs to get lost. The two of them as a couple makes even less than a binomial theorem. The Prince of Monaco met Blair while she was vacationing in Paris with S. Unfortunately for us, her little European souvenir stumbled into New York City after her. They’re engaged, and she’s pregnant, (Editor’s note: Chuck and Blair had sex while Louis and her were dating). Oooh, what will 2012 have in store? An adoption, and Louis left at the alter is what we’re asking Santa for.

Dair: Blair Waldorf & Dan Humphrey

Will Dan and Blair dare to see how their feelings fare? Constantly bickering the pair eventually became confidantes, culminating in a kiss. They are equal parts smart, sexy and sweet when they’re together. Now, that sounds like a recipe for romance.

Nate Archibald & Diana Payne

On the prowl, and back to his cougar-ish ways, Nate fell for British beauty, Diana. Lying, sneaking around and scandal ensued. Come to think about it, it’s almost the same storyline from his previous old[er] lady lover, Lady Catherine Beaton. At least, Nate got a job and a promotion with his latest affair. Ding-dong, the witch is gone, Diana has disappeared, but for how long?

Chuck Bass & Dan Humphrey

From The Matrix and marijuana emerged the unlikeliest of bromances. From season one to five, Lonely Boy and Chuck we’re barely considered frenemies. Fists and fights were their only forms of interaction, but not anymore. The pair are pals now.

Ivy Dickens/ “Charlie Rhodes” & Max Owens

From zilch to rich, these nobodys clawed their way to the top and into our hearts. (Not! Well sorta..) Charlie is one conniving creature, but we feel for her. The small town couple moved from Florida to California to pursue their dreams, before being intercepted by Serena. S dragged Charlie to New York leaving her boyfriend behind.

Serena van der Woodsen & Max Owens

The Rhodes girls have more in common than just blonde hair and good looks; they have similar taste in men. As luck should have it, Max and Serena met on the streets of Manhattan. How serendipitous! Blissfully unaware of the impending love triangle trouble, S & M began a courtship. It ended quite dramatically when Max outed Charlie and he she lied her way out, yet again.

Nate Archibald & Ivy Dickens/ “Charlie Rhodes”

While it was all a ploy to get Diana jealous, sparks flew between these two. There lies potential here. (pun intended) After she clears out the skeletons in her new Upper East Side digs, we hope to revisit this coupling again in 2012.

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