Some relationships on Gossip Girl were more toxic than others, and we just gathered the worst.

Of course, there are easy relationships to root for like the one between Chuck and Blair and the one between Dan and Serena, but what about all the toxic romantic connections viewers watched unfold through all six seasons of the show?

Here is a breakdown of the most horrendously toxic relationships each character embarked on, plus all the messy details.

Serena van der Woodsen.

Serena’s extramarital affair with Tripp van der Bilt was definitely the most toxic relationship she had on the show.

Some might argue that her relationship with Ben Donovan was a bit more toxic since he was her boarding school teacher before they started dated years later.

Others might argue that her relationship with Gabriel Edwards was the most toxic since he was willing to scam her wealthy family members out of all their money.

But ultimately, when she started the affair with Tripp, it was the worst romantic mistake. Serena made.

Tripp was married to a woman named Maureen, and she was obsessed with seeing him succeed as a politician.

He broke his marriage vows to hookup with Serena behind Maureen‘s back, turning Serena into a glorified side piece.

Then, he showed no regard for Serena’s life when he got into a car accident, moved her body into the driver’s seat, and abandoned the car for police to find.

Let’s be so for real. No other man in Serena’s life treated her as badly as Tripp.

Blair Waldorf.

For Blair, her relationships with Jack Bass and Carter Baizen are tied for being the most toxic. Blair and Jack had a one night stand, but it was incredibly sleazy when you take the fact that Jack was Chuck’s uncle into account.

Blair and Jack hooked up in secret, and Chuck felt incredibly betrayed when he later found out about it.

By the end of the show, Jack certainly prove he was capable of character development since he started treating Chuck with more respect, but the one night stand he had with Blair was still undeniably toxic and problematic.

Blair’s connection with Jack gets worse when you consider the time Chuck manipulated Blair into spending another night with Jack in exchange for the Empire Hotel.

Fortunately, Blair didn’t actually have to follow through with Jack that evening, but her relationship with Chuck was temporarily butchered.

Whatever went down between Blair and Jack was horrible, but her relationship with Carter was equally as toxic.

That’s because she only turned to Carter as a distraction while she was on a downward spiral.

Blair was sucked into the mindset of self-sabotage, and Carter weaseled his way into her bed while she was at her lowest point.

Dan Humphrey.

The most toxic relationship Dan had on the show was with Rachel Carr.

Rachel‘s approach with Dan was actually pretty sleazy, even before they took it to the next level.

Before they had sex for the first time, she was already shamelessly flirting with Dan in way that was beyond tasteless.

Rachel came across like she was holier than thou dealing with the entitled, spoiled, bratty rich kids of the Upper East Side. But, she wasn’t really that innocent.

She was supposed to be the adult in the situation, but she allowed attention from Dan to flatter her in a way that led them down the wrong road.

One social media user posted, “If it was my son and his teacher or any staff member in his school. I’d be gunning for blood. She is an adult in a position of authority. She is, at minimum, in her early twenties but most likely older. The fact that she ‘technically’ wasn’t teaching him when the affair begins is clutching at the thinnest of straws.”

Jenny Humphrey.

Damian Dalgaard is easily Jenny’s worst and most toxic boyfriend from her entire time on Gossip Girl.

He was a terrible boyfriend because at first, he acted totally uninterested in her as if he wasn’t attracted to her at all.

Then, he enlisted her help to sell drugs, which could’ve ruined her entire future. If she was arrested, she could have kissed her passion for fashion goodbye forever.

To make matters worse, he tried to pressure her to have sex with him before she was ready. He didn’t try to make it romantic or special. He told her having sex with him was a nonnegotiable.

Jenny’s entire relationship with Damian was a hot mess and it was a real hit to her self-esteem.

Nate Archibald.

Catherine Beaton was toxic a girlfriend in Nate’s life for a slew of reasons, including the fact that she was a Duchess who was fully married to another man named Lord Beaton.

On top of that, she was also having an affair with her stepson, Marcus Beaton.

She wanted to have her cake and eat it too, because she didn’t want anyone else to be happy with Marcus, even though he was in the midst of pursuing a relationship with Blair Waldorf.

One of the most toxic things Catherine did was offering to give Nate cash in exchange for sex so that she could prevent his family from going completely bankrupt. She treated him like a full-fledged male escort.

She also threatened to reveal the location where Nate’s father was hiding from the FBI if Nate ever tried to breakup with her because she was threatened by his desire to be with Vanessa.

Vanessa Abrams.

Although Chuck and Vanessa never officially dated each other in a committed relationship, they still had a friends-with-benefits fling that eventually came crashing down. Chuck was her mist toxic love interest.

This connection was toxic because Blair made a bet with Chuck to sleep with Vanessa so they could humiliate her.

If he was able to successfully accomplish that, he’d be able to have a night with Blair as well.

In the midst of the bet, Chuck realized he actually liked hanging out with Vanessa when it came to her approach to socialism and doing good deeds.

He saw that Vanessa wanted him to help her save a historical bar before it was permanently shut down.

In a later scene, Chuck and Vanessa kissed each other at an event simply to make Blair and Nate jealous.

In the episode titled The Remains of J, Vanessa and Chuck were seen getting out of bed together after having sex for the first time.

In another episode titled Southern Gentlemen Prefer Blondes, Vanessa told Dan the truth about the fact that she actually had sex with Chuck TWICE.

However, their connection started out based on a cruel bet and never amounted to anything honorable or legitimate. Talk about toxic!

Chuck Bass.

Chuck’s most toxic relationship on the show was with Alessandra Steele. He never asked her to be his girlfriend, but he continually hooked up with her because he wanted to find a way to start sabotaging Dan.

He learned that Alessandra was working as Dan’s publicist, so he knew getting closer to her would benefit him in taking Dan down.

Alessandra ended up becoming collateral damage since Chuck was never really attracted to her.

He was well aware he could have his way with her because she flirted with him at his Valentine’s Day party.

Initially, Chuck rejected her, but he later changed his mind when he realized how helpful it would be to have a woman like Alessandra in his back pocket. It was heartbreakingly toxic of Chuck to toy with her that way since she was such a kind woman.

Georgina Sparks.

Serge Ivanov was the most toxic man Georgina ever got involved with. Serge snags this title since he was exposed for being the real father of Georgina’s baby.

Viewers never got a chance to meet the Russian suitor, but we certainly heard about him as a short-lived fling in Georgina’s life.

The major detail that makes him so incredibly toxic is that he was married when he started secretly pursuing an affair with Georgina.

His scorned wife threatened to send hitmen to murder Georgina when she found out about Georgina’s pregnancy.

Because of that, Georgina went out of her way convincing Dan that he was the father of her baby as a way of trying to protect her herself.

The entire situation was out of control, and she had no business getting in bed with a powerful man who was already married to a jealous wife in the first place.

Lily van der Woodsen.

It’s hard to argue that any other man in Lily’s life was more toxic than William van der Woodsen.

In fact, the most toxic connection of all we saw for Lily on Gossip Girl was arguably her reconciliation with William.

He was a terrible husband and father the first time around because he abandoned the family leaving Serena and Eric with severe self-esteem issues.

Then later, he resurfaced and pretended Lily still had unhealed cancer so he could grow closer to her and destroy her marriage to Rufus.

William used his position as a doctor to manipulate the situation, which was beyond vindictive.

Somehow, he was able to weasel his way back into Lily‘s life and by the finale episode, they were back together. Lily deserved so much better than William!

Rufus Humphrey.

The most toxic connection Rufus had on Gossip Girl was with Ivy Dickens.

Ivy only started hooking up with him as a ploy to get revenge against Lily, and she never actually had real feelings for Rufus.

Rufus made the stupid decision to pursue a connection with her, even though she was way too young for him.

Another reason Rufus and Ivy should have never started hooking up is that Ivy also briefly tried dating his son, Dan.

Everything about Rufus and Ivy‘s connection was wildly inappropriate and strange.

Rufus’s decision to start dating Ivy was what made it damn near impossible for him to ever reconcile with Lily. He took it to the point of no return!

Lily and Ivy were feuding so hard. Rufus made it impossible to ever win Lily back when he started hooking up with Ivy.

Which of these Gossip Girl relationships was the most toxic in your opinion? Let us know your thoughts in the comment section below.