Gossip Girl featured complicated friendships and families. Enemies turned friends and then turned back to enemies. High school sweethearts turned into long-time relationships. And there was enough couple-swapping to mimic the romantic scene of a small college campus.
While some relationships in retrospect didn't seem the healthiest, there were definitely big declarations of love and romantic gestures galore. We're likely to see some repeat authors (i.e. Chuck) and some small moments made big, but all are dramatic and huge declarations of love and romance in their own way.
Olivia Clears Dan's Reputation Very Publicly
Olivia, a famous actress and played by Hilary Duff, goes to NYU briefly. During her time there, she falls for resident lonely boy, Dan Humphrey. At one point, she's interviewed on Jimmy Fallon. She tries to be more causal, off-the-cuff, and ends up telling a story that doesn't depict Dan in a good light. Granted, it's not really a negative light either, but it is an awkward story to tell on national television.
She talks about their first date and how Dan came back from the bathroom with his shirt inside out, saying that he had walked into a spiderweb. Dan is ridiculed on television. However, even though Olivia worries about Dan's reaction, he doesn't take it hard. Still, she seeks to remedy it, and on her next visit on Fallon, Fallon publicity apologizes to Dan for Olivia. This is a big gesture based on how public it was. Unfortunately, this relationship didn't last long, but it was sweet while it lasted.
Lily Helps Rufus Continue A Brooklyn Tradition
When Rufus and Lily are finally together, Rufus wants to celebrate Halloween in the Upper East Side like he would in Brooklyn. He dresses up as one of the Ramones, buys tons of candy, and tells the whole building that he and Lily will be home so that children come by for trick-or-treating.
At first, Lily humors him by staying in for the night when she had wanted to attend a party. Then, she gets the same few children to dress up differently multiple times in order to give Rufus the Halloween tradition that he wants. He does realize the trick and the treat that she's doing for him. It's a warm moment in contrast to the couple's decade-long often dramatic love story.
Serena Gives Dan Snow for Christmas
Serena and Dan are a new couple at this point, and Serena wants to give Dan a good Christmas present. With help, she creates an art installation of a winter scene. There are videos of trees and snow around them. Cut-outs of snowflakes on the door and "snow" in the room.
Serena waits for Dan on a blanket in the middle of the room. This ends up being the first place where they make love, and it's so romantic that it makes us root for this couple (in the early seasons).
Blair Says Dan's Name
This may seem small, but Blair never said Dan's first name throughout the many seasons. She always called him by his last name. For Blair, Dan went from being a nobody to a pest to a trusted friend, and finally to a boyfriend. When she was going through multiple ups and downs, including a car accident and a miscarriage, he was there for her.
Finally, she decides to choose him over Chuck. So, she rushes to Brooklyn to tell him, and she calls him Dan. Alarmed and touched, he asks her to say his name again. Laughing, she says his name many times, closing the episode and starting the "official" acknowledgment of their couple status.
Chuck Makes Blair Prom Queen
Blair's old friends decide to hijack prom, cheating the election ballots to make someone else prom queen besides Blair. Knowing how much this means to Blair, Chuck catches on to their scheme and reverses it. He puts all the votes in for Blair, swapping out the others. While he and Blair aren't officially a couple at this point (she is at prom with Nate), he does care for her, and this is his way of showing it.
Chuck Asks Blair to Live With Him
Initially in their relationship, Chuck had a hard time committing to Blair. It wasn't who he was, and while he wanted her, it was really hard for him to admit that he loved her. However, once his love was declared, Chuck was all there for Blair. When Blair was having a hard time at NYU, he offers her to stay with him instead.
She resists his invitation at first, but after a particularly brutal day in the dorms, goes to his place. Cuddling with him, she asks if he is okay. Uncharacteristically sweet, Chuck replies, "I am now," as he kisses her hand.
Blair Counsels Chuck, Reminds Him of Who He is
Now, a lot of Blair and Chuck's relationship featured Blair nursing Chuck, but this is an extra special moment. Chuck has disappeared after Season 3. After an all-time low and losing Blair, who he had been planning on proposing to, he disappears to Europe, gets mugged, shot, loses his identification cards, and decides to no longer be Chuck Bass.
Blair, in a beautiful red dress, comes to him to remind him of who he is, that changing a name can't change who you are, and to become the man that he wants to be. While she says she isn't in love with him, this scene is both a moment of mercy and a huge romantic gesture.
Dan Gives Blair Her Princess Moment
Although Blair wanted to be a princess (even in high school, she perked up at the word tiara), her marriage to a prince was less than fabulous. Dan understood that she needed to have a moment to shine as a princess. He had her dress up, took her to the Met steps where she used to lunch when she was in high school, and gave her a costume-shop tiara.
Immediately, popular high school girls (like she was) swarmed to get selfies with Blair, the princess. It's a tender moment, proving that Dan knows her, and the kiss afterward is sincere and sweet.
Chuck Tells Blair He Loves Her
In the early seasons, Chuck and Blair play a game to get the other one to declare love. Blair doesn't want to be the one to say it first because she thinks that means that she has lost the game, and therefore, lost the power. However, she decides to be honest and just say it. Unfortunately, Chuck can't seem to say it back until the end of Season 2. He talks about how he ran off to Europe, but everything reminded him of her.
Go to France, he decides to pick up her favorite macaroons for her. Go to Germany, he decides to pick her favorite stockings for her. Armed with her favorite things and flowers, he finally tells her that he loves her. He's willing to say not just once, but as many times as she requests to hear it.
Dan Writes Blair As His Great Love in His Book
This was before Dan and Blair became a couple, and Serena still had hopes for Dan. Later, Dan does end up with Serena (an ending many fans question), but at this point, his friendship with Blair is blossoming into more. And the books reveals all of this. Even Serena can see it as she tells Blair, "You're the star of Dan's book."