Blair Waldorf and Jenny Humphrey were worlds apart but more alike than they cared to admit. Throughout Gossip Girl, the two fashionistas scheme with and against each other. These two revel in the Upper East Side's scandalous drama and prove themselves to be the fiercest queens ever to rule the corridors of Constance Billard.
Like every other Gossip Girl duo, Blair and Jenny were friends one minute and enemies the next. Little J tried to emulate her Manhattan role model in season 1 before coveting the crown for herself. Queen B often worked to humiliate her successor, but the two manage to work out their differences... most of the time. Blair and Jenny were great enemies, but could they have been better friends?
Friends: They Both Love Fashion
Both Jenny and Blair display a flair for fashion throughout the series. Blair rules as Constance's queen of style before going to work with her mother. Jenny, too, works with Eleanor Waldorf as she strives to make it as a fashion designer.
The Queens of Constance were united by shared hobbies and common interests. Had they put aside their differences earlier, the two could have crafted a new fashion empire in New York City.
Enemies: Blair Banished Jenny From Manhattan
Jenny spirals during season 3 as she struggles to balance her Brooklyn identity with her duties as Queen of Constance. After a damning encounter with Chuck, the blonde draws the ire of Blair, who banishes her from the city.
Blair is heartbroken by the revelation of Jenny and Chuck's night together. Rather than trying to sympathize with her, Queen B makes it clear to Jenny that she isn't welcome in Manhattan anymore.
Friends: Worked For Waldorf Designs
Blair and Jenny's love of clothes leads them to pursue careers with Eleanor Waldorf. Both women intern with Blair's mother at different points in the series as they attempt to carve out a name for themselves in the glamorous world of fashion.
The flashforward in the series finale "New York, I Love You XOXO" shows that Jenny and Blair returned to Eleanor's to collaborate on a clothing line, putting aside their differences and becoming professionals.
Enemies: Jenny Slept With Chuck
Unfortunately for Little J, she did the one thing Blair could never forgive: sleep with Chuck. Jenny hits a low point at the end of season 3 when she seeks solace with Chuck after the young billionaire breaks up with Blair.
Jenny reveals the truth to Eric and it isn't long before the news reaches Blair. The preppy socialite is devastated by Jenny and Chuck's actions and makes it clear any friendship they had was destroyed by Little J's actions.
Friends: Blair Made Jenny Queen Of Constance
On the other hand, the only thing that means more to Blair throughout Gossip Girl than Chuck is her social status. Blair meticulously guards her legacy as Queen B of Constance. In season 2, the only contender she deems worthy of inheriting her position is Jenny, the new queen of the Upper East Side.
Like Blair, Jenny was an exceptional schemer who knew how to navigate the social politics of Constance. Blair trusted that she would make a worthy successor and gives her new power by handing her the crown.
Enemies: They Humiliated And Schemed Against Each Other
Throughout most of the series, Jenny and Blair play a game of cat and mouse with each other. Season 1 features a naïve Jenny doing everything she can to impress Blair, while the devious socialite pushes Jenny to extremes by humiliating and scheming against her.
Little J fights back against Blair's tyranny, proving she can be just as deceitful as her idol. They may have reconciled in the finale, but their history is rife with backstabbing and betrayal.
Friends: Jenny Looked Up To Blair
Initially, Jenny looks up to Blair as a role model, envying her glamorous life as a rich Upper East Side teen. In her own twisted way, Blair tries to take Jenny under her wing by teaching her the cruel realities of the world she covets.
It would have been fascinating to see more of Blair as Jenny's mentor throughout the series. The two had brilliant chemistry as enemies, but true friendship could have made them unstoppable forces in the city.
Enemies: Blair Looked Down On Jenny
Throughout the show, Blair was many things: Queen of Constance, ambitious social-climber, and a confessed classist. Blair makes no secret of her disdain for Jenny and Dan's Brooklyn background and considers herself above them due to her upbringing.
Little J may have looked up to Blair but Queen B looked down on her. The two were never truly on the same page as long as Blair refused to see Jenny as an equal.
Friends: Both Bore The Crown Of Constance
Whereas Serena often breezed through the dramatic daily events of her life, Jenny and Blair were forced to work harder to maintain their influence. Both bore the crown of Constance and understood the weight and responsibilities it came with.
Blair and Jenny had to present a perfect image as queen and were dethroned in various humiliating ways. Their shared experience of struggling to rule could have brought them closer together than Blair and Serena.
Enemies: Only One Can Be Queen
The crown brought them together and the crown tore them apart. Ultimately, Jenny and Blair were too competitive to reconcile their differences and rule together. Both had different ideologies and were at odds with each other for most of the series.
Blair wanted to be the best at everything she did and often saw Jenny as her competition. In turn, Jenny could never trust Blair and was capable of committing spiteful acts. The glamorous Upper East Siders became friends by the series finale, but their relationship wasn't without its rocky moments.