Even though he came across as a smug, teenage boy who thought he could take on the world himself, Dan Humphrey found himself in embarrassing moments throughout Gossip Girl.

Over the years, fans of the show have become more critical of him and the ways he interjected himself into the elite social circle.

This caused him plenty of moments he wasn’t proud of.

Stick around to see how Dan embarrassed himself around his childhood friend, Vanessa throughout the show.

Dan didn’t satisfy Blair in the bedroom

As a man, one of the most important things is ensuring your partner is taken care of in the bedroom.

After years of silent hostility towards each other, Dan and Blair finally gave each other a shot.

Blair was curious to see what life would be like with Dan by her side, and let’s just say she was less than pleased with how things turned out.

She was clearly looking for a lot more from her man, as both Nate and Chuck were generous lovers.

There were obviously some nerves coming from Dan’s side of the room, but that doesn’t negate the fact that Blair left their encounter feeling less than enthused about continuing a relationship with Dan.

The two continued to try and work things out, but they were doomed from the very beginning.

No matter what Dan did, Blair was never going to forgive him from his upbringing in Brooklyn.

She was always meant to be with someone like Chuck.

Dan, on the other hand, wanted Blair. Some fans even think she was his actual end goal, not Serena.

Dan sent negative Gossip Girl blasts about himself

Dan set himself up to be embarrassed on purpose, for the sole reason of thrusting himself into the elite he went to school with.

Dan and his sister always felt like outsiders, as they originally came from Brooklyn, and not the Upper East Side.

In order to make himself part of the group, he set up a website where people could send in “Blasts.”

These included things of himself, whom he nicknamed “Lonely Boy.”

There were multiple times Dan was shown at a low point, even in bed with Serena when he was supposed to be dating Vanessa.

Dan wasn’t afraid to throw shade to himself, as long as it meant he was getting close to the inner circle.

It takes a lot of self-hate to do these things to yourself, especially in high school.

For whatever it’s worth, the plan ended up working.

Somehow when all was said and done, his classmates and friends forgave him, some even understood why he did what he did.

This isn’t meant to encourage anyone in the real world to do this, though, as tons of fans online say Dan was a psychopath.

Dan hooked up with Ivy after all the harm she did

Dan knew he wanted Serena throughout the entirety of Gossip Girl, which makes his decision to hook up with Ivy Dickens even more questionable.

At first, Ivy pretended she was Charlie Rhodes, Serena’s cousin.

Her goal was to assist Serena’s aunt in getting more money from her mother, as she had already spent her entire trust.

When things started to go south, Ivy was exposed.

However, things took a major turn when Ivy was given all of Serena’s grandmother’s wealth when she passed away.

This rubbed the van der Woodsens the wrong was, as Ivy took it all for herself.

The craziest part of all was that Ivy still expected the family to love her and take her in as one of their own.

They didn’t, but that didn’t stop Dan from a night of pleasure with Ivy when he was upset at Serena.

Dan figured the best way to get back at his future wife was to hit her where it hurt the most, Ivy.

This was such a low blow for Dan to deliver and he ended up feeling truly embarrassed about it when he was finished with Ivy.

Dan dated Georgina knowing how awful of a person she was

It’s easy to look at a lot of the relationships throughout Gossip Girl and at least understand how they came to be.

One of the pairings that still leaves fans baffled to this day is Dan and Georgina.

The duo had dated in the past, but it was under totally different pretenses.

Dan assumed her name was Sarah and that she was a normal, level-headed girl who was kind and sweet.

However, Georgina reverted back to her old ways after trying out this new persona for a little while.

Most guys would see someone like Georgina and her true colors and bolt the other way.

Well, Dan isn’t most guys.

Instead, he took it upon himself to all out date Georgina, even after having the wealth of knowledge about who she was as a person.

Dan was acting crazy and desperate for love and attention, something he did throughout the entire run of the show.

He was willing to sacrifice it all when it came to Georgina.

Thankfully, the pari didn’t make it down the aisle.

But Georgina and Dan sure made for some intense storylines throughout the program.

Chuck stole Dan’s shoes and left him in the streets of New York City all alone

It’s strange to think that Dan might not have fully thought his plan of getting in with the elites in New York City through.

One night, when he was alone with Chuck, the pair were out and about in the city.

Chuck pulled a move in which he stole Dan’s shoes and left him alone late at night.

Even if you’re only a half hour from home and you know exactly how to get there, not having shoes and being alone late at night when you planned to be with people is a scary situation.

Dan felt alone and ashamed amidst the predicament he found himself in.

However, it feels almost as though justice was being served to Dan, without fans even truly knowing it.

For the longest time, Dan exposed secrets about the elite he went to school with and made them feel powerless and embarrassed, just as he did.

He never truly faced repercussions for his actions, even at the end of the show.

This was the one moment Dan truly felt how he made his classmates and friends feel.

It’s tough when you’re forced to taste your own medicine.

CeCe Rhodes told Dan he wasn’t good enough to escort Serena to cotillion

Another time Dan fell off his high horse was when CeCe Rhodes explicitly stated Dan wasn’t good enough to be Serena’s escort for her cotillion.

Dan was riding high on confidence and felt like nobody could bring him down at all.

His plan of injecting himself among his popular classmates was really starting to unfold how he pictured it.

However, CeCe didn’t exactly love the plan of Dan taking her granddaughter to cotillion.

What fans didn’t know at the time was that CeCe also didn’t approve of Dan’s father, Rufus, dating her daughter, Lily, back in the day.

She already had tons of preconceived ideas about Dan and the type of person he was.

Dan felt embarrassed that he wasn’t good enough to bring his dream girl to one of the biggest events of her life.

For whatever it’s worth, CeCe warmed up to Dan later on in the series.

She showed that growth is possible when you’re willing to accept it.

Dan got himself and Chuck arrested after getting in a fight

Few things in this world are as embarrassing as getting arrested and having to call someone in to pick you up.

Well, that’s just what happened to Dan and Chuck one night after Dan got in a fight.

The pair was out on the town and found themselves in a little bit of trouble.

It became crystal clear that Dan and Chuck would never get along in the show, as the few times they interacted only led to negative consequences.

Dan didn’t come from the same situation as Chuck, either.

There was no way getting arrested and spending a night in jail would negatively impact Chuck.

Dan, on the other hand, couldn’t afford to risk it.

He still decided to act selfishly and without taking a few moments to truly think about his actions.

After spending time behind bars, Dan truly understood what he did was wrong and that he couldn’t ever act like that again.

He learned his lesson the hard way, as being embarrassed in such a low and humiliating way typically changes most folks.

Dan was rejected from Tisch after Vanessa applied

If there was one thing made clear throughout Gossip Girl, it was that Dan wanted to be a writer and always leaned into his creative side.

Dan also thought he was the best writer in the world, which is the right thing to think.

However, at one point, Dan applied to Tisch to continue his education in the writing sphere.

He was so confident he’d get in that the rejection letter sent him into a state of disbelief.

The worst part of all for Dan’s ego was that he lost the spot to Vanessa, his childhood bestie.

Now, most normal people would be happy that their bestfriend was able to learn at Tisch.

But not Dan. He was so embarrassed and befuddled that he didn’t think Vanessa could get in on her own.

He was convinced she stole his work to make it into Tisch.

After talking to the admissions rep, he was given the spot, only to find out Vanessa had submitted an original piece of her own.

Dan not only embarrassed himself, but one of the people he held closest to in his life.

Sabotaging someone else because you were embarrassed you didn’t get in is a whole new level of low.

Dan and his family couldn’t afford for him to go to Yale

One of the other most prominent storylines to come up in Gossip Girl was Dan’s dream to attend Yale.

He envisioned himself at Yale’s English program, where he would learn how to captivate audiences with his novels.

Dan was given admittance into Yale, but there was one small problem.

See, Dan and his family didn’t come from the same family wealth that his classmates did.

Instead, they lived in a normal Brooklyn loft with other folks who lived a normal life.

This meant that his family didn’t have the funds to send him to Yale.

Ironically enough, going to such a prestigious private school might have hurt the families ability to get financial aid.

Dan still went to further his education at NYU, though.

Dan felt such a sense of shame and embarrassment when he found out he wouldn’t be able to attend his dream school, unlike all of his classmates.

Vanessa called Dan out by saying he changed from when they were kids

One of the most humbling and embarrassing things in this world is to be called out by someone who has known you for a long time, and them being right.

Well, Dan and Vanessa fit this bill to a T at a polo match.

Vanessa knew Dan as a fun, normal guy who wasn’t consumed with the glitz and glam of the fine life.

Vanessa saw Dan change over time, and not for the better.

Unlike everyone else in his life, Vanessa didn’t just sit by, she called Dan out to his face, telling him he changed for the worse.

Arguably the most embarrassing part of this was that Vanessa did this right in front of Serena, Dan’s dream woman.

Dan tried to deny this up and down, but he couldn’t.

Fans saw Dan’s attitude change throughout the show for the worse, especially early on.

Sadly, Vanessa’s words didn’t get through, as Dan continued down this road for the rest of the show.

What are your thoughts on Dan’s embarrassing moments? Which do you think was his worst? Let us know in the comments.