Nate Archibald‘s love life was always interesting to keep up with on Gossip Girl.

His girlfriend list was pretty chaotic since he ended up dating women who were old enough to be his mother and he even dated one girl who was way too young for him in the final season!

Out of all his relationships, the four most serious connections he had were with Vanessa Abrams, Serena van der Woodsen, Blair Waldorf, and Jenny Humphrey.

Nate didn’t end up with anyone in the finale of Gossip Girl, but if he were to have concluded things with a soulmate, which leading lady should he have been with?

Nate and Vanessa.

Nate and Vanessa‘s relationship was easy to root for since it seemed they genuinely had each other‘s best interests at heart.

Visually, they looked great together as a super aesthetically pleasing couple.

Some highlights between them? Nate encouraged Vanessa to take the SAT to open up the possibilities for her to attend college.

When Jenny sabotaged her with a see-through dress at a public event, he took Vanessa’s side and made sure she felt safe.

When she admitted she stole his letter to Jenny, he forgave her.

There was a lot to admire about their relationship. But they also had their fair share of negativity.

Unfortunately, he didn’t treat her the best when he canceled their summer travel plans without talking to her about it first. As a reminder, he chose to pursue an internship with his grandfather instead.

Nate and Serena.

Nate and Serena might’ve had an awesome love story to reflect on if it didn’t start on such a shaky foundation.

He had a crush on her while he was dating her best friend, Blair.

Instead of breaking up with Blair to pursue a relationship with Serena, he cheated on Blair with Serena at the Shepherd wedding.

It led Serena down a terrible spiral that ultimately resulted in her dropping out of school to enroll in a private boarding academy.

When Blair found out about the infidelity, she was crushed.

Years later when Nate and Serena tried dating in an official boyfriend/girlfriend way, their relationship was heavily tested due to Jenny’s attempt to seduce him.

Nate never cheated with Jenny, but things still didn’t work out between him and Serena.

Ultimately, Serena realized she still had feelings for Dan and those feelings were blocking her from going all in with Nate.

Nate and Blair.

Nate and Blair started dating each other in kindergarten, which means they were in each other’s lives for a VERY long time.

They were childhood sweethearts who stayed together through the night of their senior prom.

On the night of their senior prom, they decided to break up, but then later, they reconciled to see if they could possibly make it work.

But the passion between them was nonexistent, which meant they were grasping at straws trying to reignite any sort of flame.

Blair was a fiercely loyal partner to Nate who would’ve supported him in every way, but it’s clear that she was ultimately meant to end up with Chuck.

Plus, the whole time Nate and Blair were together, he seemed to have a wandering eye for Serena.

Nate and Jenny.

There was a big chance that Nate and Jenny could have had a successful relationship if Jenny wasn’t constantly showcasing her immature side.

There were pockets of time when Nate was wholeheartedly interested in Jenny, but when she did dumb things like sabotaging Vanessa‘s dress, she revealed herself to be someone Nate didn’t exactly want to be involved with.

Nate showed up like a white knight to protect Jenny from getting photographed by a sleazy photographer at one point.

He also rescued her from getting sexually assaulted when she was drugged by an evil model named Agnes.

But still, a long-lasting romantic relationship between Jenny and Nate never seemed to be in the cards based on some of petty decisions she made.

So, who was the possible person for Nate to end up with?

The answer is pretty clear! Nate should have ended up with Vanessa or Jenny.

If the actress behind the role of Vanessa (Jessica Szor) didn’t part ways with the show early, there’s a huge probability Nate and Vanessa’s characters would’ve ended up together in the finale episode.

There wasn’t a chance for Vanessa and Nate’s characters to reconnect or reestablish their love for each other since Vanessa left Gossip Girl at the end of the fourth season.

If the actress behind the role of Jenny (Taylor Momsen) hadn’t exited the show early, Jenny and Nate could have had a happily ever after moment. Taylor left the show to focus on her rock band, The Pretty Reckless.

If Jessica stayed on as Vanessa or if Taylor stayed on as Jenny, one of these leading ladies would’ve likely ended the show as Nate’s wife!

Who do you think Nate should have ended up with, when taking all of his most serious ex-girlfriend’s into consideration? Let us know your thoughts in the comment section.