Why did Serena go through so many tragic breakups on Gossip Girl? Let’s face it… the girl got around!

She dated a lot of guys and we are here to break down why nearly every single one of her romances fell apart.

Aaron Rose.

It didn’t come as a shock when Serena’s relationship with Aaron ended. He spent the majority of their relationship dating other girls and acting like a total player.

Serena wasn’t sure if he was serious about her at first, and it took him a cool minute to actually become a monogamous one-woman kind of guy.

After a while, he was ready to commit to her, but his commitment couldn’t have come at a worse time.

Bart Bass’s fake death was the talk of the town at that moment, which created chaos within Serena’s immediate circle.

Plus, Serena very visibly still had lingering feelings for Dan Humphrey.

Aaron surprised Serena with tickets to Buenos Aires for the holidays, but Serena appeared turned off by the grand gesture from him because it was more overwhelming than romantic.

She later revealed to Dan that she dumped Aaron on the airplane, right after they took off for Buenos Aires. That must’ve been an awkward flight!

Nate Archibald.

Why exactly did Serena and Nate’s relationship crumble? Nate lost his virginity to Serena on a bar top at the Shepherd wedding while he was still dating Blair.

That moment planted the seed of a relationship that would always be doomed to fail.

When they reconnected with each other during a summer in the Hamptons, it seemed they made a lot of sense as a romantic couple. She even kissed him publicly in an attempt to make Catherine Beaton jealous.

When Jenny went out of her way to seduce Nate to steal him away from Serena, Jenny’s attempts were total failures because Nate only had eyes for Serena.

Still, Serena and Nate didn’t work out because Serena wasn’t exactly the best girlfriend in the world to Nate.

She was keeping him in the dark as she was trying to track down her father with Carter Baizen’s help, and it resulted in Nate feeling super insecure about the relationship.

All Serena had to do was be honest, but she struggled with that.

What really hit the nail on the coffin for Nate and Serena‘s love story was when Juliet and Jenny teamed up to sabotage Serena‘s life.

Juliet masqueraded as Serena to kiss Dan while Jenny masqueraded as Serena to kiss Nate.

Nate and Dan were convinced they both kissed her on the same evening, so Nate decided to give up on pursuing Serena forever.

Even after he uncovered the truth about Juliet’s vindictive plan about Serena, Nate was already ready to move on with his life.

Carter Baizen.

As weird as it is to say, Serena desperately wanted her relationship with Carter to work.

She took her relationship with him seriously because he went so far out of his way to help her track down her father.

Serena and Carter officially started dating in an episode called The Lost Boy, but it wasn’t built to last because his toxic past was catching up to him.

At Lily van der Woodsen and Rufus Humphrey’s wedding, Carter was approached by a couple of men who were ready to face off against him because of a super shady thing he did to a woman named Beth.

He persuaded a sweet, shy woman named Beth to marry him so her family would pay off his gambling debts with no questions asked.

After his debts were paid, he left Beth at the altar because he wasn’t actually in love with her. Beth‘s family members, including Bree Buckley, were rightfully pissed off at Carter.

Carter couldn’t have his happily-ever-after moment with Serena because he needed to go face the music with Beth‘s family members.

In the end, Carter told Serena he’d rather have her hate him than pity him right before he dipped.

Gabriel Edwards.

Everything about Serena’s relationship with Gabriel was toxic, which is why their breakup couldn’t have come sooner.

He first showed up in New York City to convince her they should be together, even though he was secretly plotting with Poppy Lifton the entire time.

He wanted to be introduced to Serena‘s wealthy friends and family members so he could swindle them out of their money.

Along the way, he developed real feelings for Serena, but that was hardly a factor based on what his initial motives were.

In the episode titled The Wrath of Con, Serena and Gabriel ended things for good.

He apologized for the scandal and explained that Poppy was pulling the strings behind the scenes the entire time. Regardless of his excuses, Serena lost interest and they were done.

Ben Donovan.

It might’ve seemed weird for Serena and Ben to start dating in the first place since he used to be her teacher when she was a teenager at boring school.

But they didn’t technically start dating until she was well over the legal age to consent.

It’s pretty obvious Serena started dating Ben because she felt guilty about the years of freedom he lost locked up in prison based on the fact that he was accused of statutory SA by Lily van der Woodsen.

That being said, it was clear Serena wasn’t just dating Ben because she was attracted to him or excited to plan a future with him.

She was literally dating him out of guilt.

They broke up in an episode titled Empire of the Son after Ben stated he didn’t think he’d ever be able to get past the trauma of what happened.

Steven Spence.

Serena had daddy issues based on the fact that her father abandoned her, so it didn’t come as much of a shock that she eventually dated someone who was old enough to be her father.

Her relationship with Steven started on a lie since she was pretending to be Sabrina in Wisconsin when it was first revealed that they were together.

Their relationship came with its highs and lows, including the fact that he had a daughter named Sage who was only a couple years younger than Serena.

He also had cringy history with Serena’s mother, Lily.

Steven dumped Serena after witnessing her get caught up in scandalous drama with Georgina and Dan at Sage’s Cotillion event.

At the time, Steven described Serena as being too immature for him.

When they ran into each other days later at a grocery store, he told her he was open to rehashing the conversation because their breakup was a little hasty. She invited him to Thanksgiving dinner.

At the dinner, Serena lied to him by saying she had rekindled her relationship with Dan.

After Steven left, Serena caught wind of the nasty chapter of Dan’s book that was written about her and realized she wanted to be with Steven instead of Dan.

But when she tried to call Steven, he ignored her call because he was already reading the nasty chapter about her for himself.

Tripp van der Bilt.

One of the shittiest things Serena did on Gossip Girl was starting an affair with a married man.

She had no business dating Tripp, but she allowed her desire and passion to fuel her instead of her logic.

Their relationship dissolved a bit more tragically than other breakups in this lineup because it came to an end in a car crash.

Tripp got into an accident and abandoned his car after moving Serena’s body to the driver’s seat so that could stay in good standing as a politician.

Serena ended up in the hospital. It seemed Tripp truly didn’t care if she lived or died.

There was no way Serena would ever be able to forgive him or reconcile after something like that.

Colin Forrester.

Serena started dating one of her college professors at Columbia. His name was Colin, but the relationship most certainly wasn’t built to last.

Do you recall how they officially broke up?

Throughout the entire relationship, Serena and Colin were butting heads over who should make a sacrifice academically.

Should he quit teaching in order to date Serena or should she drop out of his class in order to date him?

The constant push and pull was an indicator of the unfair power dynamic between them.

Colin’s cousin happened to be Juliet Sharp, and she was ready to reveal Colin and Serena‘s secret relationship to the Dean.

Even though their relationship wasn’t ultimately exposed to the Dean, Serena and Colin still decided to breakup in an amicable way so that he could focus on his career in business rather than his career as a professor.

Max Harding.

Serena and Max were never an official couple, but they did share a kiss and they had a deep connection with each other.

Max was enamored by Serena because she was the epitome of his dream girl.

He felt like dating Serena would be a massive upgrade compared to his past relationship with Ivy Dickens.

He dated Ivy while living in Los Angeles, but when he arrived in New York City to track Ivy down, Serena was the girl who captured his attention and stole his heart.

Things between Max and Serena pretty much halted after Ivy gave Serena advice about not moving too fast with Max. Serena took that advice and canceled on a date she’d already scheduled with the guy.

After that, Ivy came up with an elaborate lie about Max blackmailing her which turned Serena off completely. Max and Serena were over before they even started.

Dan Humphrey.

Serena and Dan went through multiple breakups along the way on Gossip Girl before ultimately ending up together.

Since Dan and Serena were always meant to be endgame, the show’s finale ended on their beautiful wedding day.

Serena went through permanent breakups with EVERY OTHER guy on this list, but her breakups with Dan were never serious enough to keep them apart forever.

What do you think of all these tragic reasons behind every breakup Serena had on Gossip Girl? Let us know your thoughts in the comment section below.