15 moments in 'Gossip Girl' that were intended to be serious but turned out to be comedic gold

Early on the first season, Gossip Girl posts that Serena has lost all her friends and her potential boyfriends.

Serena sees the blast while going through old photos of her, Blair, and Nate on her phone.

But what may have been a moment to sympathize with Serena's newfound loneliness became laughable. Instead of just deleting the photos, Serena threw her phone into the trash.

The start of Blair's season-one downward spiral began with her performing a striptease at Chuck's club opening.

Gossip Girl's narration during the scene, as well as Chuck's reaction, make it clear that this worrying moment is out of character for Blair.

But watching Blair try to sensually remove her headband just makes the entire scene comedic.

When Serena and Dan start dating, Vanessa is uncomfortable with their relationship and jealous of Serena.

The two girls hang out for the first time when Dan brings Vanessa to Blair's birthday party, and Vanessa and Serena end up in a "Guitar Hero" battle.

After a lengthy sequence of party guests enthusiastically cheering Serena on while she plays "Free Bird," Vanessa steps up to challenge her back with "Cherry Pie." But before she starts, she spills a secret Dan was keeping from Serena about his mother.

Serena and Dan get into a fight over this, but it's hard to care about the tension immediately after watching Serena perform dramatic hair flips while pretending to play the guitar.

On season one, Serena and Blair are presented as debutantes at the annual cotillion.

Near the end of an episode full of drama, Chuck eggs Nate on and makes him think Carter Baizen has a thing with Blair. After sufficient prodding, Nate punches Carter in the middle of a dance.

Blair's dress is ripped when they start fighting, so she quickly walks away with Serena. But Carter and Nate can still be seen flailing on the ground in the background during the ridiculously long fight scene.

Blair decides that her biggest hurdle to getting into Yale is beating Nelly's SAT score.

To sabotage Nelly, Blair plays a Flo Rida song after hearing that Nelly's boyfriend broke up with her at a Flo Rida concert.

Blair then sets up a conversation between Nelly and her ex that causes the girl to get no sleep and spend the night before the SATs sobbing.

The situation is extremely cruel to Nelly, but knowing that a single Flo Rida song is her undoing is hard not to laugh at.

On season two, Jenny moves in with Agnes after fighting with her dad, and the two start designing a fashion line together.

But when Jenny decides to do it on her own, Agnes kicks her out, grabs all of Jenny's designs, and sets them on fire.

Jenny and Agnes are still arguing before Agnes lights the match. But instead of physically trying to stop her, Jenny just watches her work go up in flames while yelling, "What did you do?"

But it's hard to take the whole scene seriously with dialogue like Jenny screaming, "Are you insane?" and Agnes responding, "Yes, I'm insane, Jenny."

After Dan finds out his father and Serena's mother had a child together, he confesses the news to Vanessa while they're at Dylan's Candy Bar.

His decision to reveal this huge secret in the middle of a crowded candy store is already odd. And the entire scene feels more like an ad for Dylan's Candy Bar, with serious dialogue about the secret sibling added in.

The store's logo is visible in every shot of the scene, and Vanessa keeps mentioning the candy they have available by name as she talks about how amazing the selection is.

Tensions are high during the school production of "Age of Innocence" on season two.

Nate is jealous of Vanessa's interactions with the director, Julian, and Blair is trying to figure out who sent Gossip Girl a tip about her.

Nate ends up breaking character and ranting about Julian and his family's financial problems, which prompts everyone else on stage to air out their grievances with each other as well.

The moment is theoretically humiliating for everyone involved, but it's fun to watch as the usual drama unfolds with the main characters in period costumes.

Serena's mother, Lily, has a complicated past that includes multiple husbands and a serious relationship with Dan's father, Rufus.

During the second to last episode of season two, viewers find out more about Lily through flashbacks of her time in California in the 1980s.

The episode occurs during a rough period of her relationship with Serena in the present day and is intended to show how similar she and her daughter are.

But it's hard to take it seriously. The flashbacks have a noticeable filter over them, feature upbeat outfit montages, and are inexplicably intercut with present-day moments that remind viewers what the show looks like when it isn't trying to launch a failed spinoff attempt.

Not even their own high-school graduation could keep the students from reading a Gossip Girl post.

In the middle of the ceremony, Gossip Girl posts to call Nate the "class whore," Dan the "ultimate insider," Chuck a "coward," Blair a "weakling," and Serena "officially irrelevant."

Every student seems utterly shocked, even though they've read far worse blog posts about themselves.

The beeps of phones going off in the middle of graduation — combined with a close-up of Serena's tassel pinned directly to her hair sans cap — make everyone's misery comical. And afterward, the adults in the room act like absolutely nothing happened.

Dan starts dating famous actress Olivia Burke when they're both at NYU on season three.

At the beginning of their relationship, Nate shows him her "Endless Nights" movie trilogy, which includes sex scenes where Olivia pretends to orgasm. After watching, Dan is too intimidated to have sex with her, fearing that he won't live up to her vampire love interest.

The two are able to overcome this, but it's hard not to laugh at the incredibly cheesy fake-movie scene.

On season three, Vanessa and Blair compete to give the freshmen toast at NYU.

Before the toast begins, Vanessa tricks Blair into arguing with her. Blair tells Vanessa she thinks she's superior to her and admits to manipulating and lying to Chuck to steal the toast.

But Vanessa reveals that the entire speech was being picked up by the microphone she was holding, and everyone at the event overheard Blair's insults.

Blair's inability to see the microphone that was barely hidden behind an awkwardly placed bag is the least plausible secret recording since the webcam moment in "High School Musical."

Dan decides to create a modern version of "Snow White" that uses Lady Gaga songs on season three — the singer even makes a cameo on the episode.

Olivia walks onstage singing an offkey rendition of "Love Game." But she doesn't make it through the whole song because she's heartbroken after realizing Dan is in love with Vanessa.

She picks up on this during the threesome they had on a previous episode but doesn't show her hurt feelings to Dan until the performance.

It's a bizarre setup for one of the most ridiculous moments on the entire show. Plus, it's even more amusing knowing that Hilary Duff, who plays Olivia, is a far better singer in real life.

"Gossip Girl" has plenty of memorable Thanksgiving episodes, but season three's stands out for its odd choice of background music.

Before dinner even starts, Jenny confronts Eric over sabotaging her at the cotillion, Serena's affair with a congressman is revealed, and Blair accuses her mother of being pregnant.

While everyone is arguing, Jason Derulo's "Whatcha Say" plays at a bizarrely loud volume for several minutes.

It's difficult to take any of the dinner conflicts seriously when the song is on.

Georgina comes back to New York at the beginning of season four with an infant she claims is Dan's son.

Dan and Georgina co-parent for a brief moment before Georgina disappears and leaves Dan to care for the baby himself.

Of course, the baby isn't Dan's at all, and this plotline is completely ignored after just a few episodes.

Dan suddenly believing he's a teen father should be more emotional than funny. But watching Georgina hold a baby and act maternal is so out of character that all their scenes together become comedic.