TV Romance
10 Most Romantic ‘Gossip Girl’ Episodes, Ranked
“Hello, Upper East Siders,” Kristen Bell purred as the voice of Gossip Girl. In between the backstabbing, feuds, and affairs, love stories unfolded. And, boy, did we ship them.
Although many couples didn’t exactly have the healthiest relationships, they’ve still become iconic over the years – we’re looking at you, Chuck Bass (Ed Westwick), and Blair Waldorf (Leighton Meester).
Swooning away through the six seasons, the main characters went from declaring war on each other to making out the next. To remind yourself of all the grand romance sprinkled throughout its run, scroll down below and read about some of the best romantic episodes in Gossip Girl’s history.
10. "Cross Rhodes" (Season 5 Episode 16)
This might be a controversial pick. Some think Dan Humphrey (Penn Badgley) and Blair should have gotten a real shot, while others loathed this coupling. Yet, even the ones who disapprove can still see that, for a moment in time, this couple could have really been something.
Dan finally realized that he was wrong about Blair, and the enemies-to-lovers plot was set in motion. They actually were an intellectual match, but Dan getting introduced to Blair through her best friend, Serena, as her boyfriend made this situation slightly iffy.
But, then again, Nate Archibald (Chace Crawford) and Serena van der Woodsen (Blake Lively) did sleep together when he was still in a relationship with Blair, so the lines were constantly being blurred on the Upper East Side.
Dan and Blair getting closer makes this a swoonworthy episode worthy of this list. And, yes, I still believe that Dan should have picked Blair over any other woman on the show. Obviously, Blair had a stronger connection to her soulmate Chuck, but Dair had so much potential.
9. "The Unblairable Lightness of Being" (Season 1 Episode 18)
Dorota Kishlovsky (Zuzanna Szadkowski) and Vanya (Aaron Schwartz) were never supposed to be main characters, yet fans of Gossip Girl still became obsessed with the couple.
It is a rare occurrence for two characters to have that much chemistry that they become one of the most beloved items in the series. Dorota and Vanya did just that.
Their wedding was one of the most celebrated nuptials in the show’s fictional world. Blair becoming her maid’s maid of honor was a nice twist that also showed just how loving and loyal she could be.
8. "Inglorious Bassterds" (Season 3 Episode 17)
Okay, hear me out. Serena and Nate should have been endgame. Their chemistry was unparalleled, yet it was never fully explored — not in the way it should have been.
They were so compatible and matched each other’s energy. Nate was slightly kinder and less selfish than Serena, but she really was his one true love.
The perfect man for the model-like main character was Nate (or Carter Baizen, but that’s not important for this entry.) This episode was one of the times that Serena actually did something for someone other than herself. Many of those times, it was for Nate. So, it’s not surprising that she succeeded in throwing him a surprise party.
7. "Valley Girls" (Season 2 Episode 24)
Okay, was this technically allowed? No. But, was it adorable? Yes.
Chuck made sure that Blair’s wish of becoming prom queen was fulfilled by rigging the competition. This became clear when Penelope (Amanda Setton) announced that Blair won and Dan asked, “Who even voted for her?” To this, Chuck confidently responded, “Me. About 150 times.”
With a glowing smile, Blair accepted the crown, for which she owed Chuck a thank you. But he didn’t need it. All he wanted in that moment was to see her shine.
This was one of the earliest indicators that Chuck did have a good heart and that he truly cared for Blair.
This episode also deserves to be praised as the Lily backstory was quite intriguing. What a shame that the retro spinoff never happened.
6. "The Goodbye Gossip Girl" (Season 2 Episode 25)
Dramatic? Yes. Romantic? Also yes. Not only did Chuck go all across Europe to get Blair all of her favorite items, but he also told her that he loved her for the first time ever.
Another romantic plotline that occured in the episode was Rufus (Matthew Settle) and Lily’s (Kelly Rutherford) engagement. Having been each other’s first love, their complicated relationship was the healthiest one Lily ever had. When the two reconnected through their kids, it was like no time has passed at all.
Sparks were flying whenever they were in the same room, and they gave the kids a run for their money. Once they truly decided to give it a go, a whole bunch of things went wrong. However, for a while, Rufus and Lily were absolutely perfect. This was one of those moments.
5. "Summer Kind of Wonderful" (Season 2 Episode 1)
So, let’s talk about an iconic (and very steamy) episode, because “Summer Kind of Wonderful” truly was that girl. In tow with the Vitamin Water product placement, the Hamptons White Party, and insane fashion statements, this season premiere was packed with drama.
The core five characters had an eventual summer. Nate was hooking up with an older woman, Catherine Beaton (Mädchen Amick), Blair picked up a random guy in Europe, who turned out to be Catherine’s step-son, Chuck was trying to win Blair back, Dan had a wild literary summer, and Serena had been lonely.
After a few misunderstandings, Dan and Serena still found their way back to each other. In one of Dan’s most selfless acts, he walked into her world of glitz and glamour just to make her understand that he would do anything for her.
And then there was Chuck and Blair’s “three words, eight letters, say it, and I’m yours” moment. Simply legendary.
For the Nate and Serena shippers, we didn’t forget about that kiss at the White Party, which was set to Lady Gaga’s “Paparazzi.” Swoon.
4. "O Brother Where Bart Thou" (Season 2 Episode 13)
Eleanor Waldorf (Margaret Colin) started off as a pretty terrible mom, but when Cyrus Rose (Wallace Shawn) walked into her life, she changed for the better. He wasn’t exactly who Blair had wanted to whisk her mom away, but Queen B eventually became enamored with the charming guy. However, when she heard they were about to get married, she got scared.
Thinking that her mom might abandon her for a new life with Cyrus, Blair was ready to sabotage it. Unsurprisingly, the lawyer loved Blair and saw her as a daughter.
This episode didn’t just capture the feeling of romantic love, but also a love of found family.
Sure, the funeral of Chuck’s dad, Bart, also happened in this 45-minute stretch, which put a somewhat negative energy into the plotline, but he was a pretty bad dude after all.
3. "Roman Holiday" (Season 1 Episode 11)
The blossoming love of Dan and Serena was in high gear during the holiday-themed episode of Season 1. Having to work with a budget, Serena didn’t know what to buy for her boyfriend.
Not impressed by money, Dan wanted something sentimental. Luckily, with the help of his best bud Vanessa (Jessica Szohr), she knew what to do – make a snowflake installation to create a night Dan would always remember. Dan was impressed by Serena’s way of finding a budget-friendly gift that touched him deeply.
Living in a hotel, she was craving some holiday cheer, so Dan snuck a Christmas tree into her home to surprise her. This episode was truly one to remember (and take inspiration from.)
2. "The Return of the Ring" (Season 5 Episode 24)
Did anyone actually believe that Dan and Blair were going to end up together? I sure didn’t, but Dan appeared to think that might’ve been the case. So, when Blair ended up choosing Chuck over him, he was in for a rude awakening.
Blair loved Chuck so much that she was willing to drop everything, support him, and get married to him in an instant. Chuck and Blair were always soulmates. They had a twistedness that only they could match, with an adoration that compared to no other, Blair and Chuck were always meant to be together.
1. "Double Identity" (Season 4 Episode 2)
The most romantic episode of Gossip Girl didn’t even take place in New York City. In the aftermath of Chuck and Jenny’s hookup being exposed, Chuck and Blair went their separate ways. A drunken Chuck was shot in Prague and saved by Eva (Clémence Poésy). He attempted to leave Chuck Bass behind for good because he was so ashamed of how he’d hurt Blair.
After months apart, Blair and Chuck came face to face at the Gare du Nord. Blair walked up in that stunning Oscar de la Renta gown. This scene between Blair and Chuck only lasted four minutes, but it was enough to go down as one of the best in the show’s history.
Blair convinced Chuck to not run away forever. “Your world would be easier if I didn’t come back,” he said. A visibly emotional Blair responded, “That’s true. But it wouldn’t be my world without you in it.”
Blair and Chuck always got the greatest romantic lines. Even in the midst of heartbreak, their sweeping romance overpowered everything. Meester and Westwick were just astounding in this scene. And to top it all off, there’s the inclusion of Sia’s “I’m in Here.” Absolutely epic. No notes. Romance lovers, this is how it’s done.
