There were some crazy age gap relationships on Gossip Girl between couples who were not close in age at all.

Here’s your dive into some of the most jaw-dropping age gap couples that sparked between seasons one and six.

Serena van der Woodsen and Ben Donovan.

Serena and Ben first met each other when she was a 16 year-old student at boarding school. He was already in his mid-20s at that time, presumably 25 or 26.

Of course, they didn’t start dating until after Serena was older and had fully graduated from high school, but their age gap still remains.

Nate Archibald and Diana Payne.

Nate and Diana‘s age gap was beyond obvious because there was a point in time when his best friend, Chuck Bass, believed Diana was his mother.

That being said, she was old enough to be Nate’s mother as well!

Serena van der Woodsen and Steven Spence.

Serena dipped on her Upper East Side friends and pretended to be Sabrina for a little while when she started dating an older millionaire named Steven.

The relationship didn’t last, and their age gap was a huge reason why.

Steven was old enough to be Serena‘s dad. He also had a teenage daughter named Sage who was only a few years younger than Serena.

Nate Archibald and Catherine Beaton.

Another age gap relationship for Nate was his chaotic affair with Catherine.

She was getting around with a few different guys herself, but her desire to manipulate and control Nate was beyond disturbing.

Dan Humphrey and Rachel Carr.

Dan was part of an inappropriate student-teacher relationship with Rachel while he was still in high school.

Granted, he was 18 years old at the time, but the fling they had was still totally unacceptable. She was in her mid-20s, presumably 24 or 25 years old.

Serena van der Woodsen and Tripp van der Bilt.

Serena started her affair with Tripp when she was about 19 years old and he was in his late 20s, presumably 28 or 29.

One of the more cringeworthy details of his age gap relationship is that he was already married to another woman when Serena fell him.

Ivy Dickens and William van der Woodsen.

Ivy thought her relationship with William was legitimate, but he was only using her to get back into Lily‘s life.

Nevertheless, Ivy and William definitely had a secret affair going on, despite the fact that Ivy was young enough to be his daughter.

Serena van der Woodsen and Colin Forister.

Serena started dating one of her college professors, Colin, and the relationship most certainly wasn’t built to last.

At the time, Serena was 20 years old and was in his mid to late 30s, presumably 35 or 36 years old.

To make matters worse, the power dynamic of him being a professor while she was a student was not a vibe.

Georgina Sparks and Jack Bass.

Anyone who’s finished Gossip Girl in its entirety knows that Georgina ends the show as Jack’s partner.

Somehow, two of the sleaziest characters found their way to each other! Jack was definitely old enough to be Georgina‘s father.

Ivy Dickens and Rufus Humphrey.

Ivy heavily pursued Rufus because she wanted to get revenge against Lily. Rufus played into her hand and engaged in an affair with her, even though it was super cringeworthy.

Ivy was the same age as Rufus’s kids, which serves as proof that their age gap was pretty massive.

Blair Waldorf and Jack Bass.

Blair and Jack had a one-night stand together, and it was definitely the cause of some serious drama on the show.

Blair regretted the hookup session, and rightfully so. Jack was old enough to be her father, and he was also the uncle of her one true love, Chuck.

Nate Archibald and Sage Spence.

When Nate started dating Sage, it was one of the worst things Gossip Girl writers could’ve done to his character.

Nate was already well out of high school, but he started dating 17-year-old Sage anyway.

Sure, the age of consent is 17 in New York… but morally and ethically, Nate should have ended the relationship as soon as he found out how young she was.

What do you think of these age gap romances on Gossip Girl? Let us know in the comment section!